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. 

#1: A strategic CS Ops team is the backbone of a proactive Customer Success org

“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

#2: A high-caliber culture starts with your employee onboarding process

“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: 

  1. Why does the CSM role exist? The answer to this should be written as a purpose statement that’s focused on the customer, explains why CS exists in your company, and should tie back to the company’s mission.
  2. What are CSMs responsible for? Identify the specific responsibilities that CSMs have to do to fulfill the team’s purpose. 
  3. How do CSMs do their job well? Outline the mindsets, behaviors, and skill sets required to do the job well. 
  4. What do CSMs need to do their jobs well? Regularly assess whether CSMs are getting what they need to thrive: in our case, I look at 1. whether CSMs are clear on the company’s ‘why’ and the expectations in their role, 2. if CSMs have the tools they need to do their job well, 3. whether they have the messaging, training, and templates they need, and 4. how well we’re building 1:1 relationships with CSMs and creating a cohesive environment. 
  5. How do CSMs know they’re doing their jobs well? Identify the metrics you’ll use to measure how well the team is fulfilling their responsibilities.” 

— Brett Andersen, VP - Client Success at Degreed in Issue #32: Tactics for Onboarding and Developing CS Talent

#3: When presenting to executives, use data + storytelling 

“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

#4: If there’s tension between CS and Sales, it’s on the CS leader to fix 

“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: 

  1. Making sure the training for new Sales and CS hires are the same. The two training programs need to share the same messaging about how customers use the product, how the product works, what it takes to get the most out of the product, and more.
  1. Helping Sales understand what it takes to implement the product with different types of customers—in terms of time from the customer, the technical details, and everyone that needs to be involved.
    If a one-pager needs to be created, then fine—that’s on the CS leader to do. But there can’t be a difference between what the customer thinks they need to do to get setup, and what they actually need to do.” 

—Emilia D’Anzica, Founder of GrowthMolecules in “How to Fix Sales & Success Friction (Hint: It’s Not Having CS Report to Sales)

#5: CS leaders are responsible for proactively driving a customer-centric mindset across the organization 

“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

#6: Customer Success must report to the CEO

“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



This week's top posts



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.


Read the post






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 ChargebeeManish 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. 


Read the full post






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.


Read the post



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.

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