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Since launching SHH early last year, we’ve published 62 issues from interviews with hundreds of Customer Success leaders. And over that time we’ve heard some common themes — for example, a movement towards building a repeatable and shared framework around CS, building strategic (not reactive) teams, and the importance of influencing company-wide decision making.
So this week, we’re rounding up 6 lessons we’ve learned from interviews for this newsletter.
And before we dive in: I know there’s a ton of Customer Success content out there to sift through, so we’re always aiming to keep you focused on the topics that matter. Thank you for continuing to learn and help drive the function of Customer Success forward with us.
“One of things that I've leaned on to justify CS Ops is if as a CS leader you want me to make data-driven decisions then I need someone who can help me access that data. So if you start playing that out and say, ‘Let's use data, make better decisions, reduce churn by X percent— and what does that translate to dollarwise a year from now?’ The result is usually pretty shocking. Suddenly you look at that number compared to the salary of a CS Ops person and it becomes clear that it’s totally worth the risk to get even a fraction of that.”
—Beth Yehaskel, Revenue Optimization and Customer Success Architect at Winning by Design in Issue #54: 10+ CS Ops Questions Answered
“To scale, you need efficient processes; to develop efficient processes, you need good data; to get good data, you have to build the system that delivers it to you. It’s very hard to have one of those functions without the other — for example, it’s difficult to productively analyze data without having a part in selecting the data that’s available. CS Ops bundles those three functions: systems integration, business analytics, and process improvement.”
—Lea Boreland, Finance and Operations Lead at Column in Issue #26: Building CS Ops at Quorum, Aruba, and Pipedrive
“CS Ops can set you on a really solid track if you work well with them, but you don't want to underestimate or undervalue their impact. You don’t just toss ideas over and say, ‘Figure it out, Ops.’ You won't like what comes back to you if you do and whether you admit it or now, it will be your fault when goals aren’t met.
If you instead align on business goals and strategically plan with the CS Ops team, your path will be clearer. CS Ops has an incredible ability to power the team’s effectiveness towards a business goal.”
—Jeff Justice Williams, Enterprise Lead of CS at Box in Issue #53: Lessons From Running CS Ops at Zoom, Gainsight, Stack Overflow, & More
“When managers develop a winning culture, they build a team that’s fast, effective, and able to weather any storm—and the manifestation of a high-caliber culture starts with the onboarding process.
One of the pivotal changes we’ve made to our process is to plan the first week of work for the new hire. We have it all outlined in one document (linked here) that we share with them before their first day. It also includes an onboarding checklist, role expectations, software they may need access to, and key meetings and workflows. This plan alone helps new hires feel like they’re set up for success and able to quickly integrate with the team.”
—Clint Kelson, Sr. Manager of CS at CaptivateIQ in Issue #27: It's Time to Give Your Onboarding Process a Tune-Up
"The best way for Directors and VPs to ensure the success of all CSMs is to have clear expectations of the role from the beginning. We start with answering these 5 questions to clarify the role:
— Brett Andersen, VP - Client Success at Degreed in Issue #32: Tactics for Onboarding and Developing CS Talent
“The combination of clear data and the stories that tie to individual data points to provide context is very powerful in the boardroom. As a board member, we will go out and talk to existing customers, but it is not part of our day to day. Bringing those conversations into the room, along with the data and the case studies, is incredibly helpful to create the kind of discussion that you want to generate to both show the impact your CS function is having, and also to make it a focus area for the company as a whole.”
—Mackey Craven, Partner at OpenView in Issue #57: How CS Becomes MVP of the Executive Team
“Human beings, including CFOs, are motivated by stories. Tell the story. If a new deal comes in, but it’s actually an older customer who wasn’t a fan but the CSM got them engaged and turned it all around, tell that tale. Share the story that the Salesforce order doesn’t.
—Nick Mehta, CEO of Gainsight in Issue #57: How CS Becomes MVP of the Executive Team
“I found that the single best thing to do as a CCO was to build street cred—particularly with Sales. And building street cred meant getting engaged with deals. Every CS leader in existence should spend a significant part of their day being an executive sponsor for important accounts and actively involved in deals. We have a responsibility to help drive revenue for the company. If your job is solely to run focus groups and do journey mapping, I just don't think that you'll be able to make a real impact on the business and you won't be taken seriously as a real strategic leader. Get off your ass, stop managing CSMs, and start helping Sales close deals."
—Jeb Dasteel, CCO at Oracle (2008 - 2019) in Issue #60: Oracle’s First CCO on Why You Need to Help Close Deals
“Some of the most overlooked ways to improve the relationship between Sales and CS are:
—Emilia D’Anzica, Founder of GrowthMolecules in “How to Fix Sales & Success Friction (Hint: It’s Not Having CS Report to Sales)”
“One of the ways we’ve brought the customer-centric mindset to everyone in the company is to send out a weekly email to all employees that highlights one customer story. We share an example of how one customer is benefitting from our products and services. And we try to tie it to something that’s going on in the world; if there’s a big movie coming out and our products were used in the process of producing the movie, we’ll highlight that. It helps people instantly connect with the story and feel proud of what we’re doing.”
—Jon Herstein, CCO and SVP of CS at Box in Issue #15: How Box brings the customer to the forefront of their company
“Here’s how we bring the customer into the heart of our business. Instead of having a customer join us only once a year during SKO, we try to absolutely blow that up. We have a “customer takeover” once every six weeks where we give the Town Hall over to our customers. We assign certain CSMs to be responsible for hosting the event. As part of that, we always ask the customer, “What's it going to take to ensure that you stay with us long-term?” And I want them to be really explicit, to give us the cold hard truth of what it’s going to take.
This has proven to be very successful and it's given the company a greater sense of ownership. We’ve put the customer in a position where all of our people are listening. Our team members are engaged, they bring follow up questions, and they truly want to know more about that customer’s experience.”
—Pat Phelan, CCO at GoCardless in Episode #31: Bring Customers Into The Heart of Your Business, Literally
“Customer Success needs to be a strategic initiative of the company, and it can’t be a group that’s buried in Sales, Services, or Support. When you do have Success embedded in another team, CS begins to take on the behaviors and metrics of those organizations and can end up missing out on the point of “customer success” entirely. If it’s truly a strategic initiative—meaning one that’s reported to the board—then Customer Success will have the executive team’s support, it will have a defined and separate budget, and it will be equally aligned to other departments. If any one of those three things are missing, that’s a big red flag.”
—Jennifer Dearman, SVP of Global CS and Operations at Udacity in Issue #28: 5 Prerequisites for Scale with Jennifer Dearman
“I fundamentally believe that a product is nothing without the users and customers who are willing to pay for it. Therefore, the group that’s the closest to the customer—most often Customer Success—should hold an equal level of power at the executive level to Sales, Product, and Marketing.
I’ve seen too many organizations make the mistake of moving their Customer Success unit where it doesn’t have a voice at the executive level. Or, they turn it into something of a servant of the Sales or Product team. It’s such a mistake, particularly in SaaS: leaders in tech have a plethora of products with overlapping features to choose from, and they’re under great pressure to pick the right products and make sure they’re not overpaying or double paying. Companies need to make sure their products are being used by their customers and are being seen as valuable in order to survive. Customer Success is the “how”—and it needs to report to the CEO in order for the CEO to have a pulse on the experience customers are receiving.”
—Eleanor O’Neill, EVP of CS at Spacemaker AI in Issue #6: Why Customer Success should report to the CEO
DISCUSSION
What Are The Best Ways To Fail At Customer Success?
Here’s a post from Nick Mehta that’ll bring a smile to your face: “If a CEO wants to pretend they are focused on CS but really do nothing, where should they start?” Highly recommend reading through the comments.
CULTURE
What I Learnt After Unpacking One of My Best “Customer Experience” Moments
Here’s a fun exercise: consider the best customer experience you’ve encountered in the past few years and break down why it was so impactful. Director of CS at Chargebee, Manish M, did this and came up with a 2017 Qantas flight where his seat was broken. The company proceeded to go far above what was expected to make up for this loss. And what Manish realized is that “the lowlights sometimes provide us the greatest opportunity to turn around the customer sentiment and make it a truly memorable one.” Mistakes happen. What matters is how we react once they do.
COMMUNICATION
How Do You Check In Without Saying “I’m Checking In”?
Mitch Howe, CSM at Hivebrite, turned to the LinkedIn CS community to ask for advice about how to reach out to an unengaged customer with more value than an awkward “just checking in” email. This is a good thread to share with your team.
Success Happy Hour is a weekly newsletter for Customer Success leaders. Each week we feature one digestible piece of advice or a framework from a top Success leader, along with the best resources from that week. Subscribe here.
Hi everyone — Nick here. I’m taking over SHH to share an interview that digs into a hidden opportunity: the partnership between Customer Success and Developer Relations.
Developer Relations can feel like a distant, ambiguous team. But the truth is, for platform or developer-focused companies specifically, the DevRel team is out there actively working with developer communities, partnering with teams to build integrations for your product, and submitting feedback to your Product team. Not partnering with them is a missed opportunity to leverage their knowledge and relationships. And at the very least, partnering with DevRel will help you understand what they’re submitting to Product that may be prioritized over your customers’ requests.
I interviewed Bear Douglas (Director, Developer Relations at Slack) and Teresa Nesteby (Developer Support Manager at Slack) for this topic. We covered:
Here’s their perspective.
Developer Relations is becoming an increasingly important priority for platform and API-driven companies. But it’s also a role that can be interpreted very differently depending on what a company does and where DevRel sits within the org structure.
"Developer Relations (DevRel) is an interdisciplinary role that sits in a border space between product, engineering, and marketing.”
-Bear Douglas, Director of Developer Relations at Slack
DevRel responsibilities in API-driven companies
In API-driven companies (think Twilio, Stripe, SendGrid), DevRel tends to act more as a go-to-market function — recruiting developers to use the platform — and is usually nested within Marketing. A lot of the team’s work is around outreach, customer education, webinars, and talks. And their KPIs tend to be based on things like top-of-funnel growth, community engagement, conversions of new developer customers, or expansion within those customers.
DevRel responsibilities in platform companies
In platform companies like Slack, Facebook, or Twitter, DevRel tends to be grouped within Product or otherwise strongly tied to Partnerships and the Business Development organizations. You can think of the DevRel team in these companies as the ones advocating for the platform with developers, and advocating for developers with the Product team. They provide the training, materials, and consulting when individuals or teams want to build an integration for the product. And they feed back real-world bugs and feature requests to the Product team.
“Ultimately Developer Relations is responsible for your platform’s developer experience.”
-Reto Meier, Developer Advocate at Google
At Slack, our DevRel team has team members with specific areas of focus: some people are focused on writing API documentation, some build tools or integrations for developers, and others run feature alphas and betas for the Product team. Each group is evaluated on hitting KPIs in their specific focus areas. For example, team members focused on API documentation are measured on delivering high-quality documentation on time. (For more on how teams are measured, here’s an article on how DevRel career ladders work at Slack.)
Editor’s note: since Bear and Teresa’s backgrounds are with platform companies (reporting into Product), that’s where we focused the rest of the interview.
Some companies, like Slack, have a Technical Customer Success Manager team (aka “Technical Architects”) and a DevRel team. In most cases, Technical CSMs are focused on contract-based work with specific customers — and their focus generally surrounds “administration“ work. DevRel teams are focused more on scale than helping customers one-on-one; they’re creating lots of enablement materials, webinars, etc., that help developers build integrations on the platform.
Here’s how a CS leader might think about a useful partnership between the Developer Relations team:
If I were to share a couple of pieces of advice with CS leaders, I’d say this:
CSMs want the product to be sticky, and what better way than to embed additional integrations and use cases, however technical they may be, in the customer’s existing workflows?
The best CSMs are willing to get deep with technical speak but at the very least, CS teams should consider DevRel as a resource to pull in when those discussions go beyond their technical knowledge. Then on an ongoing basis bring DevRel in to train CSMs on the new integrations and other areas of the product they’re working with, and how they might be used with certain types of customers.
THE ROLE OF THE CCO
Say Goodbye to the Tactical CCO — Here’s What Strategic CCOs Focus On
"If you want to influence Sales, help them close deals. Period." This thinking helped Jeb Dasteel, who pioneered the CCO role at Oracle, pave the way for other strategic CCOs to know how to approach their role. In this piece he goes deep on how top CS leaders can move from being tactical to strategic, including focus areas, key metrics, and common pitfalls.
MEETINGS
QBRs and EBRs Are Things of the Past
Russ Dury, CS Lead at Zeplin, makes the case that too many business review meetings focus on the company and not the customer. “Why do you think your customers skip EBRs with you?” This article is a good reminder that customers are busy and if your meetings with them aren’t tailored around their objectives, you might as well not waste their time.
COMMUNICATION
Nonviolent Feedback
When giving feedback, are you using words like I like it, this is good, awesome—or the reverse, bad, sucks, lazy? In this piece, Zef Hemel calls this “violent feedback.” He argues to remove subjective language from your feedback and instead state 1. the observation, and 2. the impact of the observation.
SELLING
The 4-step Secret to Upselling
Annie Gray, Director of CS at LiveHelpNow, with some useful tips for CSMs to build trust while upselling. Consider passing this quick read along to your team.
Success Happy Hour is a weekly newsletter for Customer Success leaders. Each week we feature one digestible piece of advice or a framework from a top Success leader, along with the best resources from that week. Subscribe here.
There are a few distinct handoffs in a typical B2B company: when a customer is handed from Marketing to Sales, and Sales to CS. When product specs are handed from Product to Engineering. Each of these handoffs are well documented and given plenty of attention.
But there’s a distinct handoff between CS and Product too, involving customer feedback on the product. And in the world of SaaS, this handoff is too often treated haphazardly: feedback is “handed off” in google sheets, in Slack, in one-off meetings.
All that’s to say, the Product <> CS partnership needs some shaping up if we’re to get Product to prioritize our customers. So to help us know how to be more intentional, we held a roundtable with Megan Bowen (CCO at Refine Labs), Jeff Justice Williams (Enterprise Lead - CS at Box), and Nick Paranomos (CPO at ‘nuffsaid) on this topic.
Here’s a summarized version of the highlights from that conversation. If you want to watch the recording instead:
Q: What practical steps have you taken in the past to have an equal amount of influence relative to your other peers on the e-staff and, more specifically, equal to the Chief Product Officer?
Jeff: I'd say that the first step is for CS to have a formal seat at the table. There are a lot of companies that don’t have that space open for CS to be able to present what the post-sale experience looks like at depth, the same way that Sales does for the pre-sales flow.
If you don't have someone at that top level, then there's a gap. So if your company has a CPO, but the highest level of CS leadership is a senior manager, it’s likely there's an innate disconnect on the executive team’s visions and how their organization plays into the customer journey.
Another situation that is very common, which is more misleading, is when the highest CS leader has a bloated title (think VP or Director) but they're really acting as a player coach. This is a disservice across the board internally and to the customer, and it makes it very hard for us to have a true voice in the journey.
If CS and Product are going to have a peer-like relationship, the company has to have a CS leader who is vision-bound and forward-looking. And both the CS and CPO leaders have their hands on the customer journey.
So for me, bottom line, the first step is to give CS a genuine seat at the table.
Megan: One way to build an equal amount of influence at that level as a CS leader is to have the mindset that you are the CEO of the business. You’re thinking “what is actually the most important problem that needs to be solved in the business as a whole?” You’re not just focused on your own department.
If you can look at the business from a 30,000 foot view, see areas we’re missing out on or the biggest pain points across the customer experience, then build a business case around improving that—that’s when you get invited to the exec meeting. That’s when you have an opportunity to drive the agenda.
Nick: I think the one thing that CS leaders can do—and I don’t think most people are tracking this right now—is you need to make your CFO, your best friend. Start learning the language of the CFO and the metrics they care about and how they think about the business. Because what I've seen with the most powerful members of the executive team is they start with a metric that matters, and then they have causal metrics that the team can affect and take action on.
So for example, the CMO has marketing qualified leads. They've got channels with funnels and they can tweak what they do with those funnels. Every meeting they come and say, “this is how we affected that KPI.”
It's the same thing with the CRO—dollars closed. And the CPO—usage. Both the CRO and CPO know what levers to pull that have downstream effects on their KPIs.
But many CCOs aren’t there yet. We’ve got NRR as our outcome, but we’re using things like NPS and CSAT which aren’t leading indicators of NRR. It’s very difficult to create a causal relationship between NPS and NRR.
Instead, what I typically recommend for companies that I've worked with in the past is this: think about your customer journey, break it down into risk stages, and think about the actions needed from all teams across that journey to move the needle on my end metric.
Q: How have you seen success in developing a comprehensive health score that takes all team metrics into consideration? And how much ownership does Product have in this process?
Megan: For a meaningful health score, there are three main things you need to take into consideration:
So it starts by thinking about those three buckets and then figuring out based on your business, your context, your product, what makes sense to measure against that. I think it needs to be quantitative, but there should be a little bit of qualitative input.
Now, what I will say is that after creating lots of “too sophisticated” health scores with all kinds of criteria, what I've actually found as most effective is a system for flagging at-risk accounts. Basically, it’s identifying signals that things are off for a customer. If they’re not logging in, sure, that’s a flag. If they’ve logged 50 support tickets in the last 30 days. If you survey them at the end of the onboarding process and they don’t feel they’re fully onboarded yet. Those are all at-risk indicators, and acting on those has been more meaningful to move the needle on churn.
Nick: Yeah. One thing I’d say is, look, product usage is my job. If any Product leader out there is telling you that usage is on you, they're dead wrong. My job is to make sure that the product is good enough that people are using it. If they're not, that's on me. That's what I'm held accountable to. So for organizations that have product usage as a core metric for CS performance, that is the first place to start—we need to agree that that's on Product.
Second, I hear a lot of the churn reasons coming from Customer Success, sharing things like “my champion left,” “we lost budget,” “it wasn’t a good fit.” Those things are not helpful to me. What I want from CS leaders is to collect better data. I don’t want to know once a quarter after a QBR if the customer is happy or not. I need an automated way to know if each champion is doing well and how they feel about that product.
So Megan, to your point, I need to know how you feel about your support interactions. I need to know how you felt about onboarding. Did my sales team over-sell you? Does the product meet your expectations? How do you feel about your service level and our response time? The thing is, if usage is going well, we may still have a problem. If it's not going well, we definitely have a problem.
I need to focus on the “we may have a problem” part and I need better data to inform what’s going on. So what I typically recommend is setting up some sort of automated survey that's specific to different areas of the account during the onboard, engage, and renew stages, where we can actually get data about the customer’s experience.
Q: Nick, who is the best partner within Product to work with every day? Is it the CPO or someone on their team?
Nick: Well, first the CS leader and the CPO have to align on what process we're going to use to include customer data in Product’s decision making.
The CPO probably doesn’t want anything to do with it after that because their team is making the prioritization decisions. So the CPO and CCO need to agree on a process where somebody from CS is representing the customer voice in sprint planning meetings for each team that’s working on those areas of the product.
And in order for anything to get prioritized, we need the voice of the customer in that meeting. So whether it's a CSM, or a CS manager, or even a director of CS that sits in these meetings, depending on your company size, that's where the ongoing partnership needs to happen.
Q: And what needs to be included from CS in order for Product to effectively make a prioritization decision?
Megan: I think a lot of teams struggle to present information within the context of the customer’s pain points, and the opportunity to be gained (or what could be lost) from a dollars perspective. That’s the only way you’re going to effectively influence change in the organization.
That’s often hard for CS leaders because as you get promoted and come up through an organization to a leadership position, that is not something that you’ve had to learn as you lead up to your new position. So they have to figure it out on the go.
Apart from that, I’d also add that it’s dangerous for Product teams to make decisions in a conference room because they think they know what’s best. I’m not saying you should do exactly what the customers say, but their perception is their reality. And if that’s not part of Product’s decision making process, they’re missing an important part of the puzzle.
Jeff: That level to level forum, between the Product team and the Customer team, is key. It means your ICs are engaged, your executives are engaged, and Product isn’t making decisions in a conference room.
One final thing I’d say is if you have an attachment to that old algebraic adage, CS (Customer Success) = CX (Customer Experience) x CO (Customer Outcomes), and if you’re putting your Marketing, Sales, Customer Success, and Product team next to that conversation, you’re on the right path. Align team members, align goals, and constant communication. There is no over-communication between the Product and the CS teams. It's just about intentionality and presence.
LEADERSHIP
My Leadership Document—2021 Edition
Here’s one to bookmark. This excellent list of Subbu Allamaraju's leadership beliefs and behaviors is filled with noteworthy advice like “To create a high performing team, you must help others grow as leaders,” “set unarguable goals,” and “use your expertise to ask better questions to promote thinking but not to dispense opinions.”
ALIGNMENT
The Intersection of Customer Success and UX
Kim Oslob, Sr. Director of Customer Engagement at MeasuringU, offers her perspective on the benefits of having CS and UX more closely aligned.
LEARNING
A Guide To Customer Exit Interviews
In this post, Anita Toth shares a blueprint for how to think about, plan, and conduct a customer exit interview. As she smartly points out, “as [customers] prepare to leave, you have a rare opportunity to find out why.”
Success Happy Hour is a weekly newsletter for Customer Success leaders. Each week we feature one digestible piece of advice or a framework from a top Success leader, along with the best resources from that week. Subscribe here.
It was 2008 when Jeb Dasteel was named Chief Customer Officer at Oracle, after leadership roles in Sales, Consulting, and “Customer Programs” at the company for 10 years. “I didn’t know a single other CCO at the time,” he recalls. “Everything we did, we had to make up as we went. Trial and error. We did some smart things and some dumb things, but by and large, we were successful and learned a lot along the way.”
Jeb left Oracle in 2019 and now advises CCOs on how to refine their customer strategy. He notes that especially in the past two years, he’s impressed with the quality of modern CCOs — but CS leaders still have gaps to fill to become an established member of every executive team.
Nuffsaid co-founder, Nick Paranomos and I interviewed Jeb on how Customer Success leaders can become more influential executives. Here’s an excerpt from our conversation. (You can also read the full interview here.)
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Chris: Here’s a controversial statement that I’d love for you to react to: The CCO will never be a strategic member of the executive team unless they own a number that matters for the business.
Jeb: I agree with that in a lot of ways. I've talked to so many people who would argue that the CCO has to report to the CEO and they cannot have a quota responsibility. I tend to agree on the CCO needing to report to the CEO, but I don't think it's absolutely essential. If you are a great leader by influence you can be under the CMO, the CRO, or the head of Service delivery and still be highly effective depending on the culture of the organization. The worst thing you can do is create the perception that the CCO’s job is somehow apart from the day-to-day objectives of the rest of the company.
I disagree with the idea that CSMs cannot be responsible for renewal revenue. For many organizations, it works really well. I don't buy into the idea that CCOs should be disconnected from the business in not having some of those strains and pressures. There is a middle ground.
When I was the CCO at Oracle, I had the latitude to fail fast—to take risks that I knew were iffy, but to keep it under the radar and completely screw up and try it again. I would not have been able to do that had I had quarterly quota attainments. However, I did feel tremendous responsibility to help Sales sell. I was deeply involved with the Sales teams every single day.
Chris: So in a world where you're a head of CS, and your Sales peer is a dictator, your Product peers or Engineering peers are egotistical maniacs, your Marketing person’s head is always in the clouds, and somehow you're supposed to drive the resources of the organization, how does one level up their influence on the executive team with those peers?
Jeb: Here’s what I did. I managed by influence rather than trying to have line authority over everyone. Of course I had my own team, but the whole purpose of the team was to influence the rest of the organization, drive change, experiment and try things out and then deploy them where they best fit. But the purpose was never to own—and definitely never to be in competition with the rest of the organization
I found that the single best thing to do as a CCO was to build street cred—particularly with Sales and Engineering at Oracle. And building street cred meant getting engaged with deals. I would not have been successful at Oracle doing anything as a CCO had I not actively engaged with the Sales organization to close deals.
There shouldn’t be a CS leader anywhere in existence that doesn't spend a significant part of their day being an executive sponsor for important accounts and being very actively involved in deals and issue resolution. We have a responsibility to help drive revenue for the company.
If your job really is to run focus groups and do journey mapping, I just don't think that you'll be able to make a real impact on the business and you won't be taken seriously as a real strategic leader.
Chris: That might be the best advice I've heard in a month, which is if you want to drive influence at the executive level, help close the deals.
Jeb: Exactly. Get off your ass and get on an airplane. And I'll tell you what, this was by far the most rewarding part of my job. Even after essentially 100% of Oracle's products became available as a cloud service and we had CHROs, CMOs, and CFOs as customers, the principal person I worked with for 21 years when I was at Oracle was the customer’s CIO. If I knew 100 CIOs around the world, I always felt a responsibility to maintain those relationships, advocate for those customers, and help drive business because of those relationships.
So I made it my job to be, and I know this term dates me, the human Rolodex for the top 100 CIOs in the world. Because my job was to know them and have a relationship with them so I could call them and have a conversation. There were so many times where the rep or the strategic account manager requested that I call the CIO because they didn’t have that relationship. I would also become an executive sponsor for many of those customers.
Now, I couldn’t be an executive sponsor for every account, but I could get on airplanes four or five days a week, cover a lot of area, and be a valuable resource by putting myself in the position of doing a warm handoff and setting the relationship up for success.
I believe every CCO should operate that way. There's literally no substitute for engaging with customers.
Chris: How can a CS leader know if they’re too tactical and not strategic enough? Are there any common pitfalls that would reveal a leader is being too tactical?
Jeb: There are two dimensions here. There's tactical versus strategic and process versus results. I think you're too tactical if you're more process-oriented than you are results-oriented. And the symptom that reveals being too process-oriented is that you're not focused on the results for your own organization by focusing on your customer's results.
To me, there are two litmus tests to understand if you are an effective CS leader:
1) Whether you are actively engaged with the Sales organization to drive business.
2) Whether all the customer feedback being collected and analyzed is being actioned upon.
If it's a “no” to either of those two, if for example feedback is just fodder for interesting conversation, it’s a complete waste of time. And actually, it’s worse than a waste of time—it's counterproductive. You will be labeled as a person who does some “interesting stuff,” but never delivers any real outcomes or results.
MANAGEMENT
The 25 Micro-Habits of High-Impact Managers
Here’s a list packed with tips on how to become the manager your team needs. A few of my favorite pointers include “Think of yourself as the team captain, not the head coach,” “Spot chances to send kudos up the chain,” and “Reserve time for thinking outside the box.”
CROSS-FUNCTIONAL PARTNERSHIPS
What Product Wishes Every CSM Did
Tanuj Diwan, Head of Product at Surveysensum, points out some areas CS teams can focus on to create a better partnership with Product.
CULTURE
Why It’s Difficult to Build Teams in High Growth Organizations
Here’s an article on two core challenges of scaling a team: team structure, and culture. The author reminds us to put in place some ways to reinforce culture at scale, when the “newbies” outnumber the veterans.
RELATIONSHIPS
What To Do When A Customer Wants to Cancel A Contract
Jason Lemkin, founder of SaaStr, with this quick list of what you can and should do when a customer wants to leave. It’s difficult but “remember that by the time a customer asks for their money back—it's too late. All you can really do is make them leave as happy as possible.”
Success Happy Hour is a weekly newsletter for Customer Success leaders. Each week we feature one digestible piece of advice or a framework from a top Success leader, along with the best resources from that week. Subscribe here.
In her new book, Onboarding Matters: How Successful Companies Transform New Customers Into Loyal Champions, Donna Weber offers a blueprint for delivering a world-class onboarding experience.
This week’s newsletter features an excerpt from the book, where Donna highlights the importance of a customer enablement content strategy for customers and gives a step-by-step plan for building out this motion at your company.
No matter how much your customers love them, your CSMs still shouldn’t be the ones delivering training. The 2020 Customer Onboarding Report reveals that most respondents are yearning for courses to lead customers to quick wins. They are desperate for self-paced content to scale onboarding and enablement for both new and existing users.
At Ace Analytics, we leveraged courses, documentation, help articles, and other customer enablement offerings to expand the reach of the onboarding program and the CSM team. We plugged the right content for the right users into the right parts of their onboarding and adoption journey through a learning management system and email campaigns. The impact: well-trained customers were more likely to renew and had higher Net Promoter Scores.
Companies that hire me also find a correlation between well-trained customers and higher adoption and renewal rates. At a company that provides software for accountants, the renewal rate for trained customers is 50 percent higher than for untrained customers. At a company that provides process automation software, trained customers are over 150 percent more likely to renew, with 50 to 70 percent higher annual contract values. While this is impressive, both companies suffer from having a small percentage of customers in the well-trained category. This drives home how important it is to scale customer enablement: You have to widen your reach. Single CSMs training an individual, or even small groups of people, to use the product won’t impact your business bottom line.
When it comes to customer enablement, there’s a huge opportunity to profit from the useful approach mastered by the professionals in Customer Education. Customer Education scales Customer Success to onboard and enable your users in four ways: with a one-to many model and with offerings that are repeatable, role-based, and hands-on.
1. One-to-many model. While Customer Success is usually a one-to-one or a one-to-few approach, effective training is designed to be a one-to-many approach. Courses are developed for repeatable delivery, provided by many instructors, and attended by multitudes of customers. Once seld-paced courses, or tech-touch, enter the picture, the reach scales exponentially, with little to no cost for each additional person enabled.
2. Repeatable content. Instead of having each CSM creating unique classes for individual customers, dedicate resources to design and develop repeatable content that enables customers along their lifecycle. A benefit of this approach is that customers receive a consistent experience, so the success of the learning is not dependent on the particular CSM assigned to them.
3. Role-based. Rather than "drinking from a fire hose" to learn the whole product at once, people take the specific courses designed for their unique roles, at the appropriate points in their customer journey. A best practice is to modularize learning and to provide just-in-time enablement.
4. Hands-on. What most CSMs call training is not actually training. A high-level product overview and demonstration as part of onboarding doesn't provide the effect it should. A more effective approach is to provide hands-on, interactive training that is specific to the work people do in your product. Interactive courses are especially important because when customers retain what they learn, they no longer lean on CSMs for training.
Customer self-sufficiency reduces the load on both Support and CSMs, allowing all teams to manage more accounts as your company grows. The more specific, interactive, and hands-on the training, the more users retain what they learn, and the less internal teams need to continue supporting customers on basic tasks and “How-to’s.”
Rather than waiting until you have a team of curriculum developers and instructors, start scaling with these simple approaches.
1. Assign a resource. Instead of directing each CSM to do their own thing to enable customers, move content development responsibilities to one or a few team members to build re-usable content. Is there someone on the team that usually jumps in to build content? If so start with them. There might be a CSM you dedicate to building content for the whole team, or assign as your first Customer Education resource. Take what they build and share it across the team.
2. Talk to CSMs. Understand where customers need help, focusing on general use cases that can be used across multiple users.
3. Talk to Support Agents. Review the top ten "how-to" cases logged and create simple training modules so customers can help themselves rather than log support tickets.
4. Talk to customers. Find out what customers need to learn and how they want to learn it.
5. Apply the 80/20 rule. When developing content, apply the Pareto Principle, or the law of the vital few. With a "less is more" approach, produce content to increase customer skills, rather than increase customer knowledge. This means you show users the main routes, or "highways," they need to reach their destination, not every possible side street.
6. Build a few basic courses. Pick a role and a use case or two that you gathered from interviewing CSMs and Support agents. Remember to specify what users need to do in your product, not just your product features.
7. Produce "cheap and cheerful" courses. Keep production values simple, especially if your product is constantly changing. Don't spend much time on high production quality unless you know your customers demand it.
8. Set up a process. Help CS and Support teams explain where and how to point customers to existing, standardized courses, so they don't have to build and provide the content themselves.
At what stage should you invest in a dedicated Customer Enablement resource? As soon as possible. Customer training and enablement are that important. If customers don’t know how to use your software, they won’t adopt it, and they won’t renew their contracts. Start simple and assign a resource to handle initial course development and delivery. Your education resources can grow as you bring in revenue. When you charge for training, which we’ll cover in the next chapter, you can invest the revenue into building the team and developing a robust training offering.
Use your Customer Success teams for what they were hired: strategic, high-value tasks, specific to each customer. Moving CSMs out of ad hoc, repeatable tutoring and coaching keeps them focused on building stellar relationships with their accounts. Building repeatable ways to onboard and enable new and existing customers means you have a greater impact with your onboarding program. Keep it simple and improve as you go. You can’t afford to wait.
As you build customer onboarding and enablement content make sure you don’t create a tangled jungle that customers have to wade through to find what they need because odds are when customers struggle to find information to use your product effectively, they won’t adopt your product, get value from it, or renew. Also, a content jungle will negatively affect your company due to the added costs by employing expensive resources to fill the gaps, duplicating content, and using overlapping tools and systems.
Avoid content jungles by coordinating your content strategy:
1. Consider forming a “content council” with representatives from every group that creates content to take inventory of customer-facing material and uncover gaps where there’s no content.
2. Rather than building every new enablement approach from scratch, curate from different teams. Curating allows you to quickly drive users to product adoption by leveraging what’s already available. When you know what needs to be conveyed to customers, then parse out who creates each deliverable and in which format. The priority is to divide and conquer, rather than replicate.
3. Build learning pathways. Show users the progression of content in context of a visual, role-based learning path, easily accessible on your website.
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Big thanks to Donna for allowing us to publish this chapter. Be sure to check out the full book here.
LEADERSHIP
Managing Up - Lessons from Scaling Teams at Credit Karma and Lyft
An excellent, clear-eyed look at what it means to effectively manage up. Some gems from the piece: “Many professionals already know that empathy is extremely important when managing down; however, they seem to forget this lesson when it comes to managing up.” And “When faced with a difficult situation, effective upward managers package the problem in a way that makes it easy for their manager to provide help.”
STRUCTURE
Do SMBs Need Customer Success? 100% If You Also Have Sales Involved
Jason Lemkin, founder of Saastr, makes the case that if your product is complex enough to have a Sales team, you need Customer Success too. Onboarding a customer with “A wiki, some self-service Q+A, and a bunch of bots” is not enough.
CAREER
10 Lessons from 10 Years in Customer Success
Brett Matthews, Customer Success Director at Salesforce, helps us level-up by condensing his experience into a list of learnings. I enjoyed reading all of his advice, and especially points #5 (“Enable Success Within Customer Success”) and #6 (“Know Where to Put Your Calories”).
Success Happy Hour is a weekly newsletter for Customer Success leaders. Each week we feature one digestible piece of advice or a framework from a top Success leader, along with the best resources from that week. Subscribe here.
I believe the psychology of the customer’s emotional experience is a building block for Customer Success. By definition, the “customer experience” is the sum of every interaction a customer has with your business. So the emotional experience is a lot like psychology: it’s how these interactions are translated into thoughts, feelings, and behavioral responses.
“After I began practicing Customer Success I realized that, in a way, we are the customer's psychologist.”
In life, everything is personal and driven by emotions, especially in business. So to fully understand the psychology of the emotional experience and why that understanding is a building block within Customer Success, let's start by breaking down psychology. Psychology is focused on four main goals: to describe, explain, predict, and change the behavior of others. Effective psychologists identify needs and drive confidence through transparency. The same can be said in CS: we need to describe, explain, and predict outcomes for our customers. And we need to use transparency to develop trust with customers.
To accomplish this, we need to identify the right emotion or sentiment our customers display and also understand what drives or triggers a positive emotional experience. Then we can use this information proactively in our day-to-day interactions. Effectively implementing and using these understandings is a key element of moving from reactive to proactive CS mode.
There are a few reasons why understanding a customer’s emotional experience throughout their journey is important for those practicing Customer Success.
“Effective psychologists identify needs and drive confidence through transparency. The same can be said in CS: we need to describe, explain, and predict outcomes for our customers.”
Without identifying and measuring emotions, it would be impossible to evaluate your customers as individual personas and accurately assess account health and relationships.
My team uses six pillars to set the tone of our customer relationships and as a guide for nurturing positive emotional experiences. Utilizing these elements gives us a chance to set positive experiences from scratch.
These six elements are aligned closely to basic human psychological drivers. Therefore they apply to Customer Success and wherever there are human connections and emotions involved.
In the last year, it’s been critical for my team to track and measure a customer's emotional state. After I saw Ziv Peled’s relationship coverage model, I had an “aha” moment. I realized that while we were a mature CS organization by many standards, with well-defined processes and risk assessment, we were only looking at the account level. We treated accounts as one flat unit—a vague thing while ignoring the fact that different personas behind the account should design the health of an account.
We didn’t recognize that each persona has a different perspective, experience, relationship strength, personality, and internal relationships to manage. The bottom line is that it's a subjective ecosystem that should be treated as such. And we weren’t doing that.
Armed with this insight, I knew we needed to analyze customer relationships differently by giving dedicated attention and weight to each one of the personas by implementing a relationship model. To create an accurate picture of customer health, my team of CSMs track two areas. The first is relationship strength. I have CSMs go through each of their customers and rate the relationship on a scale of four levels.
The second dimension of our relationship model is gauging sentiment. We have a simple model of three levels: positive, neutral, and negative. We test the emotion the customer feels towards our brand, product, and service on this range.
Measuring these two areas and being able to see them on a dashboard has given us a very complex and holistic way to assess the real risk of an account. Along with developing a more accurate picture of customer health, using a relationship model will build more long-term relationships where customers will serve as growth agents and ambassadors.
Equally as important, having a relationship model in place will allow you to know exactly where to put more focus and give you precious time when something goes wrong. Why? Because when you measure your relationships by persona, you are reducing your chances to be surprised.
MANAGING YOURSELF
Bad Execution vs Good Execution
Julie Zhuo, author of The Making of a Manager, simplifies what “good” and “bad” execution looks like in 10 tweets. One example: “Bad execution is picking two—time, quality, or cost. Good execution is thoughtfully choosing the scope such that things are built on time, on budget, and at a high level of quality.”
DECISION OWNERSHIP
I Want to Hire Someone My Team Said “No” to on the Debrief
“Committee-driven decisions are almost always conservative… Especially for decisions that could carry lots of downsides - like hiring the wrong person - group decision making can result in most of the ‘maybe’ cases turning into a ‘no’.” I’m a fan of Gergely Orosz’s writing, he’s always thoughtful. Here, he shares his thinking on how to manage disagreements on hiring.
FOCUS
How the Best CEOs Use ‘Thinking Time’—According to an Executive Coach
All of these points could be applied as a busy CS leader: talk to customers (“If you already have a good relationship with your customers’ executives, you can smooth the way when issues pop up with one phone call”), build your talent bench, become a thought leader.
PERSPECTIVE
How Zendesk Adapts Best Practices in Product to Customer Success
Here’s Teresa Anania’s take on measuring the impact of CS and why they focus so heavily on Time to Value
Success Happy Hour is a weekly newsletter for Customer Success leaders. Each week we feature one digestible piece of advice or a framework from a top Success leader, along with the best resources from that week. Subscribe here.
Wayne McCulloch just published The Seven Pillars of Customer Success. His new book outlines an adaptable framework for building a strong Customer Success organization and is packed with detailed examples of how companies have put his seven pillars to the test.
This week’s newsletter highlights an excerpt from the final chapter of his book where he shares predictions about the future of Customer Success—and makes the case for why “reporting to Sales” won’t be part of that future.
You can read the rest of his predictions and more by ordering the book here.
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The future of customer success begins with finding its rightful place in the organization: doing so will directly impact the function’s effectiveness. Correctly placing CS within your organization will unleash its full power.
Customer success (or more specifically, the owner of the customer journey) should report directly to the CEO. I notice a lot of nondigital-native companies develop customer success functions within their organizations under sales. This is a mistake; this trend prevents the CS function from fulfilling its obligation and reaching its true potential.
You tend to find CS reporting to Sales in larger, traditional companies more often than in young, modern ones (or younger companies with digital native leaders). Leaders in traditional companies are extremely experienced experts in their industries but often have little to no experience with the SaaS and cloud-based tech movements. Considering customer success is a function born of those movements, the disconnect is easy to see.
In the next 4 sections, I’ll dive into the origins of this disconnect and 1) how the pre-subscription era mindset led to the common practice of CS reporting into sales, 2) what organizational complications develop alongside this org structure, 3) the “death spiral” that can occur for both teams when CS sits under sales, and 4) the huge benefits of having customer success report to the CEO.
This trend, having CS report into Sales, isn’t happening intentionally—it’s happening as a result of a pre-subscription era mindset that simply isn’t as effective in today’s subscription-model world. In the pre-subscription era, the head of sales ruled the roost. They were the person responsible for the majority of the company’s revenue and was thus a very powerful person in the organization. Back then, all revenue was tied to sales (and a little piece from services or support functions). It didn’t matter if it was new customer acquisition, retention, or expansion. Before subscription-based business models, sales got credit for it all.
But all that started to change when the subscription economy arrived. Suddenly, customers no longer needed to pay a massive amount up front. Instead, they were asked to pay monthly. This transactional change also inspired a change in the way customers expected to see value. In the past, it would take years to implement software and drive to adoption. Today, customers expect to see value on day one. If they don’t, they will cancel their subscription and go somewhere else.
Land and expand is the motion of increasing sales. Older companies and executives try to shoehorn sales hunters into farmers missing the true value of a customer success organization. It’s not about selling more licenses (traditional sales model); it’s about exposing value and helping customers achieve their desired outcomes. This comes from CS management.
And these changes caused business leaders to have to put more emphasis on retention, which if you think back to the very first chapter of this book, was the first wave of customer success. Customer success was born to focus on retention so sales could focus on new customer acquisition.
In the first wave of CS, when the function was a baby, there were no complications in the way it was structured because no one noticed a problem. But what do you think happened when companies started to grow? What do you think happened when CS started to own more revenue than sales from retention?
It resulted in a massive complication. “I’m the head of sales or chief revenue officer. I should own all the revenue. CS should report to me.” Traditionally, sales owned all the revenue, and seeing larger revenue dollars sitting under a different department looked weird—and ruffled a few feathers. But over time, if a business is successful, expansion and retention revenue will increase proportionately faster than new business revenue. It’s just math.
Salesforce, for example, renews more than $20 billion in revenue each year, but their new customer acquisition revenue is much smaller than that. They can’t sell $20 billion in new revenue annually. Customer success has the job of retaining revenue from customers who have been using the platform for 20 years. It’s just easier to retain $20 billion in revenue than it is to newly acquire it.
So it’s also no wonder a lot of CEOs place customer success under sales. Sales has traditionally been responsible for all revenue and CS works to retain revenue, so tying the two together makes sense and can seem like the simplest org structure option. Another reason why CS commonly sits under Sales is because this practice may lessen confusion around expansion. As much as people want it to be, expansion is never black and white and it’s hard to draw a solid box around ownership of expansion.
These are the reasons why a lot of CEOs place CS under sales, but I’m here to tell you that’s all wrong! Customer success should report directly to the CEO (or at least a CCO).
I’m not alone in this thinking either. Dave Kellogg (who previously worked at Salesforce) wrote an article about this. He claims that when CS reports into sales, it’s detrimental to both teams. You want sales to focus on sales. When CS reports under sales, the sales team gets sucked into account management issues such as renewal challenges and transactional expansion conversations.
The idea seems collaborative, but it’s actually destructive. Sales is a really, really hard job, and I challenge anyone who thinks otherwise to put themselves in a salesperson’s shoes. Try to sell
against your competitors and live off your commission check. Sales is hard, and you need your salespeople to focus on it without any distractions. New ARR has to be their metric of success.
Customer success suffers, too. When the function sits inside sales, it forces the CS team to be support oriented (like it was in the past) rather than growth oriented. CS exists today because the old way of doing things needed improvement. It was created to fill in the product gaps. But as you’ve seen in each of the pillars, CS has grown into a growth engine. When the CS team reports under a sales organization, they are pushed into a support role. They aren’t empowered to expand business or identify advocates.
When a CSM isn’t driving value, they are more likely to handle support issues themselves. They want to create value somewhere, so they work tirelessly, with restricted resources, until they get the job done. This creates a death spiral. On the other hand, when a CSM is responsible for expansion, they are more likely to behave in a way to help expand an account rather than retain an account.
When you build compensation plans and operational models correctly, CS will flip major expansions over to sales, and sales will flip incidents and insights back to customer success. This means CS will find sales opportunities and share them with sales, and sales will find areas of improvement and share those insights with CS. You don’t want your farmers competing with your hunters and vice versa, do you?
Another advantage of separating the two is that it creates another professional avenue for your sales professionals. Instead of closing three deals a day, they can have access to 10 to 20 customers with transactional expansion opportunities. Once they learn the ins and outs of how customers operate, they can transition back into a sales role. Keeping the teams separate creates an easy and beneficial way to rotate employees around the company.
Separating your CS and sales team creates an internal system of checks and balances. Oftentimes, salespeople are tempted to book new business they know won’t renew.
“I know you don’t have any support people and can’t afford this $200,000 product, but I’m going to help you out. I’ll sell it to you at an 80% discount.”
The salesperson is motivated by new ARR. If they need $40,000 to get to their number, they’re going to make that deal every time. They are incentivized to close new business. We’re telling them to do this.
Regardless of the lack of renewal, a smart SaaS company doesn’t want that customer’s business anyway. They will inevitably be the customer who is always in trouble and always calling support for help. These are the customers that escalate issues and create a lot of noise inside the organization. There is nothing about this situation that’s good.
Customer success is measured on gross churn and has a strong incentive to call the sales team out when they make deals like this. “This isn’t a smart deal for us. This customer isn’t going to renew, and they aren’t equipped to manage the product internally. They’re going to cost us money. We need to pass.” Separating the teams creates a natural checks-and-balances system and suddenly you’ve got two executives at the same level having a conversation about what’s best for the company, not what’s best for the individual team.
When CS and sales each report to the CEO, Sales can stay focused on new customer acquisition and CS can focus on growing customers.
INTERVIEWING
Your Customer Success Interview Blueprint
Maranda Dziekonski, SVP of CS and People at Swiftly, shares the interview plan she’s been using and refining for the past 7 years. Complete with the qualities to look for within each section of the hiring process and exercises to assess a candidate's ability to succeed at your company, it’s worth the bookmark.
CULTURE
How to Build a Customer-First Culture
Hubspot’s CCO, Yamini Rangan, defines what it really means to put the customer first. Apart from learning about the values and practices HubSpot has in place, I enjoyed reading the story about Tesla’s customer philosophy to “make them talk about you at dinner tonight.”
SCALING
The Judicious Imposition of Structure
Here’s Executive Coach Ed Batista, with a thoughtful piece on why larger companies need more structure. Plenty of examples in there worth reading, but I found his tips on “the leader’s calendar” and how that evolves at scale especially useful.
Success Happy Hour is a weekly newsletter for Customer Success leaders. Each week we feature one digestible piece of advice or a framework from a top Success leader, along with the best resources from that week. Subscribe here.
This week we launched the first ever magazine for Customer Success. It's titled 2.0. And the inaugural issue explores how successful CS leaders elevate their role by giving customers a seat at the decision making table.
So for this week’s newsletter, we’re highlighting a section from the magazine—my Q&A with Dione Hedgpeth (Chief Customer Officer at Sumo Logic). Dione has led an incredible career: she ran Support and Services at Mercury Interactive for 10 years, building their first CSM team back in 1999 when, as Dione says, “there was no one to copy but Salesforce.” She led Customer Success at Pano Logic, Precise Software Solutions, and then Apptio before joining Sumo Logic as their Chief Customer Officer.
Dione recognizes how increasingly important Customer Success has become over her career. “20 years ago when we were doing support and services, no one really cared,” she says. “But now in SaaS, customers are the lifeblood of the company. It’s been incredible to see how this role has evolved and grown over time.”
In this interview, Dione shares how Customer Success leaders should think about designing and advocating for their organization and where she sees the function of CS headed. To read the full interview with Dione (+ interviews and advice from CS leaders at Box, GitLab, Gong, and Gainsight), grab a copy of the 2.0 magazine.
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Chris: It’s interesting, you really have been doing the equivalent of Customer Success for 20 years even if it wasn’t called that. What are some mistakes you’ve made around team structure that you’ve learned from and wouldn’t repeat?
Dione: One mistake I’ve made and have seen other people make is trying to create the org structure first. Doing this doesn’t make sense—you have to look at the product and the go-to-market motion, then break that down into all the activities needed to drive that motion. Once you have all the activities, you determine what skills are needed to drive those.
And then once you have the skills, look at how often those skills happen. Are they daily activities, or are they activities that happen once a quarter? Because then you can design a team around the core activities, and determine who will own the activities that aren’t happening as often.
We have to break down the work first so the roles and org structure become obvious. But I’ve seen people starting with the org structure and roles first—they decide they’re going to have a CSM or an AE or a CS Engineer before considering the motion and activities that truly need to be filled. It’s backward.
Chris: Can you give other leaders advice on how to advocate for Customer Success as a function within their company, and specifically when advocating for budget?
Dione: My opinion is that the data should speak for itself.
And what I mean by that is, I don’t think there’s some magic percentage of revenue that should go towards existing customers versus new ones. Some CS teams should be at 20% of revenue and some at 5% depending on the complexity of the motion and what it takes to drive the motion.
The work a CS leader needs to do when they first come in is to actually break down the activities and count the hours. The level of investment will vary based on what work needs to be done. The math is obvious to you after you’ve mapped that out. Finance people don’t care about your stories, they don’t care about your feelings or how busy your people are. They want to see a work breakdown structure and a capacity model.
So that’s always the first thing I do when I join a company: I partner with finance and partner with my team to break down the activities, then roles, we need.
I’m also a big believer in doing a journey map because you can’t break down the activities until you get cross-functional alignment on what the desired customer experience is. I’ve brought in a consultant twice now to help us run the journey mapping session with sales and product people, and people really close to the customer. We break down the activities, then we break down the hours, the skills, and the roles. We have finance work with us on the numbers, the capacity plan—and you’re done. Advocating for budget is an exercise around data.
Chris: You’ve seen this industry evolve for 20 years. How do you think the role of Customer Success leadership will evolve in the next five years?
Dione: I have so much I could say about that topic. But speaking broadly, what often frustrates me is how nascent this industry is. With Sales leaders, there’s a methodology that exists. There’s a funnel, there’s velocity in the funnel; the revenue engine is mature in Sales.
Customer Success is no different. It’s just no different. That’s why, for me, doing the journey mapping, breaking down the activities, having phases, measuring the velocity, it’s what’s needed to have a mature CS revenue and retention engine. Customer Success leaders need to be thinking about their funnel. Right now it feels like while it’s evolved a lot over the past 5 years, it’s still so new, people aren’t thinking of it like that. But I believe it’ll look different in the future.
STRATEGY
How to Drive Over 100% NRR With SMBs
Jason Lempkin highlights data from PagerDuty, Box, and Shopify to make the case for launching a second core product earlier.
CULTURE
We Need to Talk About Your Q3 Roadmap
“Your coworkers—and maybe you, too!—are at the end of their rope...and as the product roadmap chugs along, something’s gotta give. And I think it’s going to be your [timelines].” Here’s Lara Hogan with a timely message, and tips for helping teammates get the breathing room they need.
PROCESS
Managing a Customer Success Team, With Boaz Maor
Boaz Maor, CCO at talech, shares a list of principles for managing a growing CS team. Here’s one that stuck out: “early on, over invest. You simply have to make those early customers successful, even if you can’t create an ROI analysis to back up the investment. The success of growing, expanding, and scaling out depends on that early success.”
Success Happy Hour is a weekly newsletter for Customer Success leaders. Each week we feature one digestible piece of advice or a framework from a top Success leader, along with the best resources from that week. Subscribe here.
CS Operations is an up-and-coming role within Customer Success. If we’re to get up to speed and create CS Ops roles within our companies that are focused and effective, we ought to learn from how other teams are doing it. That’s why this week, I’ve enlisted the help of CS Ops experts to answer 15 common questions about their role, function, and more.
Note: I recently posted this question on LinkedIn. Click here to see what other CS leaders had to say.
“No matter what, even if Customer Success is sitting under Sales, CS Ops needs to sit squarely with the broader Customer Success team reporting to CS leadership. This is crucial for proximity, visibility, and awareness of the deep nuances of what's happening within the post-sale motion.” —Jeff Justice Williams, Enterprise Lead of Customer Success at Box
“CS Ops is best suited to sit with people who have very similar skillsets so they can collaborate and load-balance between different roles. So having CS Ops within the CS team allows Ops to really focus on the top needs and understand those needs in detail for the CS org.” —Seth Wylie, Head of Customer Success Operations at Gainsight
“Not necessarily intentionally, but when CS Ops reports into Sales it always seems to come secondarily to the needs of the Sales team and the Sales Ops activities. Having CS Ops report into CS and being very close to the leadership there has consistently been the best way I've seen it work.” —Beth Yehaskel, Revenue Optimization and Customer Success Architect at Winning by Design
“One of things that I've leaned on to justify CS Ops is if as a CS leader you want me to make data-driven decisions then I need someone who can help me access that data. So if you start playing that out and say, ‘Let's use data, make better decisions, reduce churn by X percent— and what does that translate to dollarwise a year from now?’ The result is usually pretty shocking. Suddenly you look at that number compared to the salary of a CS Ops person and it becomes clear that it’s totally worth the risk to get even a fraction of that.” —Beth Yehaskel, Revenue Optimization and Customer Success Architect at Winning by Design
“I like having enablement (training, marketing materials, etc.) under the CS umbrella because that role needs to know the specific tools, processes, workflows, and data that are relevant to the CS org. Having the enablement team really tightly tied into Customer Success makes sense.” —Marco Innocenti, Senior Leader of Customer Success Operations at Zoom
“This is a struggle for Ops in general. When my previous boss said he would love to get a better sense of what a performance-based bonus would look like for the CS Ops team, I didn't know where to start. When I spoke with Sales Ops and Finance, they were just sort of like, ‘Eh, we kind of do a thing.’ So I don't have a great system for that. I think that there are things you could use like MBO’s, an internal NPS, etc. But I carry a little bit of a chip on my shoulder about performance-based bonuses. I just prefer the salary approach. We've leaned towards that, but every employee at Gainsight also has a company-wide bonus that's part of their comp.” —Seth Wylie, Head of Customer Success Operations at Gainsight
“I've seen companies look for their first CS Ops hire when their CSM team matures from reactive to proactive—shifting from firefighting and triaging to proactively guiding customers along a specific path to achieve key milestones that enable value realization. CS Ops then partners with CSM leaders in designing, operationalizing, and continually evolving these proactive strategies.” —Sonam Dabholkar, Director of Customer Success Operations at Gong.io (201-1,000 employees, 51-200 team members in CS)
“It can often depend on whether your company uses a low or high-touch model and average customer value. If it is a low-touch model, a CS Ops person could be your first CS hire. That person could build customer communication automation and reporting, and then from there hire CSMs to start engaging where the opportunity warrants the investment. In a high-touch model, I think it is still wise to hire one CS Ops person from the start, but that often is not seen as the highest and best use of funds at that stage. If your company does not hire CS Ops from the start, here are a few signs you need the function:
"Scalability and bandwidth issues of frontline CSMs are both key indicators of the need to introduce repeatable and potentially automated processes. If there is a need to build or buy third-party tools to support is another flag that it is probably a good time to look at hiring a CS Ops professional." —Michael Haygood, Director of Customer Operations at Multiple Companies (201-1,000 employees, 6-50 team members in CS)
“CS Ops spans a wide range of responsibilities, so it’s important to be purposeful about defining what your first hire will focus on and what level of depth they’ll go to in each area. Key items will typically be systems, forecasting/reporting, hiring planning, team process, special projects, and possibly enablement. Based on my experience being on and building CS Ops teams, for a first hire I would look for someone who 1) has broad CS ops experience, and has touched all the areas above 2) can act as a true partner to your CS leader - someone who will bring suggestions and make their work better 3) has worked at a company that has made it to the next major milestone your company is trying to reach and has ideally seen that transition. *Bonus points if they have experience working in CS themselves because that will give them a leg up in understanding your team and providing recommendations.” —Jackie Lusardi, Senior Customer Success Operations Manager at Drift (201-1,000 employees, 51-200 team members in CS)
“I have prioritized analytical skills and attention to detail as key attributes for anyone being added to the CS Ops team. Refining processes and scaling customer communication requires a lot of data review and validation. Having a "good eye" and being able to perform and understand Excel lookup functions sets the foundation for clean data and an ideal automation environment.” —Karen Blue, Customer Success Operations Manager at CentralSquare Technologies (1,001-5,000 employees, 6-50 team members in CS)
"Systems/Tools Admins: we need people who love making the tools work for our teams. Data Analytics: someone to help make data-driven decisions. Project Management: a skill that allows us to continue to drive both CS Ops and CS projects as a whole." —Robert De La O, Director of Customer Success Operations at Menlo Security Inc. (201-1,000 employees, 6-50 team members in CS)
“First you must align to your company’s Go-to-Market (GTM) strategy and Objectives & Key Results (OKRs). You want to set the expectation that your team is a strategic partner and not a reactive support group. If you are aligned and influencing the GTM strategy, and your team is driving towards the overarching company objectives, it is easier to prioritize what work is most important and what gets moved to the backlog. Second, manage CS Ops like a product where your stakeholders and CSMs are the customer. Implementing an agile methodology will help you collect and prioritize tasks through a backlog, breakdown complex, cross-departmental projects into manageable sprints, create flexibility to address changing business needs, set a regular cadence and change management process for releasing new functionality, and establish a measurement framework to test and monitor adoption and impact.” —Renee Burrell, Senior Director of Customer Success Products & Operations at MarketStar (1,001-5,000 employees, 51-200 team members in CS)
“In our low-touch segments, CS Ops focuses on workflows and alerting, all based on health and churn analysis. In a sea of customers, our goal is to help those 1:Many CSMs prioritize their time and mitigate risk. With our high-touch segments, we help the CSMs focus on diving deeper to better understand each customer's engagement, sentiment, and usage. —Chelsea Leavitt, Senior Customer Success Operations Manager at Drift (201-1,000 employees, 51-200 team members in CS)
“Adoption Rate, Churn Rate, NPS, and Post-Sale Revenue.” —Kate Paliakova, Director of Customer Success and Operations at Logyc Co.
“All of them! We align ourselves closely to the overall CS Org metrics of CARE - Customer Satisfaction (NPS, CSAT), Adoption (Users vs. Features), Retention, and Expansion. If we are doing our job then we can easily spot risk and trends in our healthscores and provide feedback to the teams we support on how they can better engage with customers.” —Robert De La O, Director of Customer Success Operations at Menlo Security Inc. (201-1,000 employees, 6-50 team members in CS)
"There are three types of metrics Customer Success Operations teams should be paying attention to. The first type of metrics is the company level KPIs the Customer Success Team is responsible for impacting. Metrics such as, the Net and Gross Renewal Rate, Net Promoter Score, and/or Active Usage Rates. As a Customer Success Operations team your primary responsibility is to enable the Customer Success Team and operationalize the customer journey, and to do this effectively you need to continuously monitor the performance of the team and how your efforts are impacting those overarching metrics. The second type of metrics to pay attention to are process performance metrics. This will help you monitor the performance and impact of the business processes and systematic workflows you implement to support customer success initiatives. Is the new onboarding process reducing the customers time to value? Is the new risk playbook being adopted by the customer success managers? What are the click-through rates on automatically triggered product adoption emails and are we seeing an increase in product adoption as a result? The third type of metrics are your Customer Success Operations Team's productivity and performance metrics. This could come in the form of managing completion of quarterly objectives and key results, customer satisfaction scores from your Customer Success Management team, or agile performance metrics to monitor the quality, quantity, and velocity of work completed." —Renee Burrell, Senior Director of Customer Success Products & Operations at MarketStar (1,001-5,000 employees, 51-200 team members in CS)
“The increased efficiency of your front line CS colleagues. We should see and measure our impact internally by how we free our team’s time to engage with customers. Also, increased QBR output, consistent quality of engagement, and increased high-value activities are all interesting measures of program success.” —Michael Haygood, Director of Customer Operations at Multiple Companies (201-1,000 employees, 6-50 team members in CS)
"We hold ourselves to the same metrics and goals that we put on the CS team. If they are hitting their retention and health goals, then we know we are doing our job as well." —Chelsea Leavitt, Senior Customer Success Operations Manager at Drift (201-1,000 employees, 51-200 team members in CS)
"As an Ops team, we use Salesforce, JIRA, Tray, and Zapier to manage most of our work. We also have a tool called Sonar that is helpful on the Salesforce systems side." —Chelsea Leavitt, Senior Customer Success Operations Manager at Drift (201-1,000 employees, 51-200 team members in CS)
"Our CS Ops team uses Gainsight. It's our one-stop-shop for most of the data that we use and the automated "Calls to Action" and tech touch communications that we set up." —Karen Blue, Customer Success Operations Manager at CentralSquare Technologies (1,001-5,000 employees, 6-50 team members in CS)
“We have 2 (hour-long) regularly scheduled meetings with CS leadership every week. The first, at the beginning of the week, is focused on CS Ops projects and updates. This would be where we propose any new set of work or we talk about outstanding questions. This has been a helpful forum for presenting our ideas and priorities. The second is a meeting we call "CS Metrics” and is on Friday. This meeting focuses on presenting data and findings to leadership. CS Ops owns portions of this meeting, along with other CS leaders. This is a great time to highlight findings in the data and make recommendations based on those facts and observations. It is helpful to back up what you're saying with proven data.” —Chelsea Leavitt, Senior Customer Success Operations Manager at Drift (201-1,000 employees, 51-200 team members in CS)
"I meet with our head of CS weekly, we have CS Ops roadmap team reviews monthly, and quarterly roadmap org updates. We also have project plans and syncs as needed to get feedback, circulate questions, and get clarity." —Michael Haygood, Director of Customer Operations at Multiple Companies (201-1,000 employees, 6-50 team members in CS)
“CS Ops should be in close sync with other operational teams in the company that sit in other functions, e.g. Sales Ops, Marketing Ops, Business Ops, Finance. Quarterly planning sessions and bi-weekly meetings with the leaders of each team facilitate ongoing alignment of priorities and sharing of key updates. Using a central project planning tool and consistent project methodology also helps these cross-functional teams seamlessly collaborate.” —Sonam Dabholkar, Director of Customer Success Operations at Gong.io (201-1,000 employees, 51-200 team members in CS)
“I think there is a realization that customer-focused teams have not had the operational support that Sales and other teams have typically had. As we start to better define CS Ops we will have more clear career paths, communities of interest, and a sharper focus on how operational excellence can drive better customer outcomes.” —Robert De La O, Director of Customer Success Operations at Menlo Security Inc. (201-1,000 employees, 6-50 team members in CS)
"I'd like to see CS Ops expand beyond what I've been hearing lately, which is "lives under CS leadership, focuses on CSMs." We should think more broadly about the entire customer journey and make sure to be in a position to see a more holistic view of how the customer is experiencing your brand and product through various stages. This might mean staying close to those team members working pre-sale, to understand the buyer journey and carry that over to the post-sale team. It could mean diving in with your services organization and ensuring teams are coordinating their strategic approaches with clear ownership." —Chelsea Leavitt, Senior Customer Success Operations Manager at Drift (201-1,000 employees, 51-200 team members in CS)
"I'm increasingly seeing CS leaders (VP of CS, CCO) work closely with CS Ops to not only operationalize key initiatives but also as an innovative thought partner to guide and evolve the CS strategy. I believe we'll see CS Ops involved more in this space, and will also see a clearer career path formed from CS Ops to CS executive roles." —Sonam Dabholkar, Director of Customer Success Operations at Gong.io (201-1,000 employees, 51-200 team members in CS)
“I believe there will be an increased demand for CS Ops over the next 5 years and will see overall less economic growth over the next 5 years than we saw the past 5 years. Because of this I feel many companies will orient themselves toward increasing productivity per CSM, as priority over/instead of leveraging increased headcount. This will drive the need for increased automation and increased productivity per team member. These are two of the needles CS Ops can most directly impact.” —William Buckingham, Customer Success Operations Manager at Delphix (201-1,000 employees, 6-50 team members in CS)
ADVOCATING FOR CS
What if There Were No CSMs?
Here’s Nick Mehta, CEO of Gainsight, with an interesting angle on how to justify the need for CSMs: evaluate what would happen if you removed CSMs from the equation.
INDUSTRY
The Art and Science of Customer Experience
“What we’ve learned from [delivering delightful customer experiences] at scale is that there is an art and a science to delightful customer experience.” Yamini Rangan, CCO at Hubspot, offers her perspective on why customer experience has become more important for B2C and B2B alike, and what customers are demanding from their buying experiences today.
PROCESS
How to Design and Implement an Effective Onboarding Process
Here, Lincoln Murphy has fleshed out (in detail) 4 tactics to build out an effective onboarding strategy. He offers some back-to-the-basics reminders like defining what it means for a customer to be “onboard.”
COMMUNICATION
On Speaking up and Shutting up
“It took me a long time to realize that A) the impulse to stay quiet is a signal to speak up, and B) the impulse to say one more thing is a signal to stfu.” Here’s Ed Batista with a concise and thoughtful post on the role emotions play in how we contribute to discussions.
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