If you ask any halfway decent Sales leader about their strategy, you’ll get an answer packed with tangible details, frameworks, methodologies, and hard numbers.
But ask a Customer Success leader about their strategy? Sometimes it’s not as clear. And fair enough. Sales as we know it has been around for decades. CS…not so much. Either way, we’re willing to bet that not every CS leader is fully confident about their high-level strategy.
CS has traditionally been far more about service—onboarding, implementation, making customers happy—than revenue.
But CS teams are increasingly responsible for the single biggest source of potential revenue: current customers.
If you’re a CS leader these days, now’s a perfect (and important) time to step up your game. I hate to break it to you, but you’re in Sales. To stay competitive and keep growing your business, then it’s time to act like a salesperson.
Here’s how CS leaders can steal from Sales and take their rightful place at the grown-ups’ table.
Get serious about numbers and accountability…like a Sales team
Sasha Anderson came into her role as Head of Customer Success at Procore by way of Revenue Ops. Her first priority when she moved into leading a CS team was to adopt a more rigorous, sales-style operating cadence.
For Sasha, this wasn’t about “fancy technology” or adding more complexity. In fact, the CS team at Procore started by simply adding a weekly forecast call to discuss renewals, risks, and opportunities.
That mental shift did (and continues to do) wonders for her team; everyone is consistently being held accountable for “knowing what’s going on with their accounts” on a weekly basis at a minimum.
And this isn’t just an exercise in “rolling up numbers to our executive team,” Sasha says. She clarifies that forecasting based on the qualitative insights from Customer Success Managers (CSMs) and quantitative data on each customer’s actual behavior has made a huge difference.
Here are the three components Sasha’s team covers each week on those forecast calls if you’re curious:
1. Account inspection
They go account by account and address questions about basic customer hygiene:
- What’s their health score?
- When did you last update their forecast category, and what methodology did you use to make that decision?
- Do you have any qualitative notes on the relationship with the customer?
- When was the last customer meeting?
For Sasha, these questions really come down to one thing: “Are you working this account or not?”
2. Likelihood of renewal
Next up, renewals. Sasha and her team look at how likely the customer is to renew, and why. She recommends breaking the renewal segment of the call into four key talking points:
- What's your relationship with the customer?
- Are you multithreaded within the account?
- Do you have a buyer champion?
- Does the customer attend your meetings?
- Do you have executive sponsorship?
- What’s the customer’s usage data like?
- Are they using sticky features?
- Are they maxing out their licenses?
- Are they getting value from your product?
- Are you giving them value that directly ties into their main business objectives?
- How many different departments are using your solution?
- Are there any gaps between what the customer wants from your product and what it can do? If so, how much of a problem are those gaps?
- Have they installed integrations?
3. Overall trends across a CSM’s book of business
Once you’ve looked at the bottom-up customer data, Sasha recommends spending time considering the overall CS data story, too:
- What’s the trend for your gross retention?
- What's your trending net expansion?
- What’s the trending rate for deal size and deal cohorts?
Once you’ve put all this quantitative and qualitative data together, you have a well-informed picture of your team’s post-sales forecast and a consistent weekly habit.
Turn your team into a lean mean CS machines
Building better habits is tough for everyone. It can feel tedious and frustrating to add new processes, like those weekly forecasting calls. Sasha has four tips for getting buy-in from your CS team when you’re introducing new, more rigorous operational processes:
Explain what’s in it for them
You’ll struggle to level up to sales-grade operations if your team thinks you’re just doing a box-checking exercise for leadership. Instead, advocate for these new processes and tools as ways to make work easier for your CSMs. You could even put a variable compensation plan in place to up the ante for CSMs and give them a way to reap the rewards of retaining and expanding their customers. And if you already have a variable comp plan, you can absolutely speak to the financial reality; good sales coming from CS means more income for CS professionals.
Focus on the information that moves the needle
Don’t expect to gather as much information in CS as you would in Sales. “CS people are working way more accounts than new logo sales,” Sasha points out. A commercial CSM could be working 70 to 100 different accounts. It’s not feasible to expect them to document a six stage sales journey for each account.
Instead, Saha recommends that you focus on four or five key metrics that are most important from a hygiene perspective, and prioritize keeping those data points up to date.
Give Operations chores the attention they deserve
Here’s a more nuanced caution: Be wary of outsourcing forecasting or updating customer information to Operations, warns Sasha: “Your managers need to be the ones holding their teams accountable for keeping their accounts up to date.”
Don’t be a coach who’s afraid to play the game
As a leader, you have three responsibilities, says Sasha: “To set the tone, the pace, and the standard for your organization.”
When you’re introducing this new, more demanding approach to CS, you should be leading by example. Sasha preps collaboratively and asynchronously for forecasting calls with her team leaders every week. In her words, “If they know that I’m looking at the renewals every week, they know they need to be looking at their renewals, too.”
Map everything you do back to revenue
Conor Nolen is the CCO of Drata, and he reports directly to their CRO. For Conor, this doesn’t just make business sense — it’s also a source of job security.
“Especially in today's economic landscape, there's nothing more insulating than being a contributing factor to the most important metric right now, which is the revenue of your organization. You know, the softer sides of things right now, frankly, are at risk.”
Conor urges CS teams to broaden their thinking beyond customer care, customer support, and NPS scores, and focus their attention on how CS directly impacts revenue outcomes.
His top two tips for how CS can speak the language of revenue:
Tie your work into the revenue systems of record
Thinking like a salesperson means making damn sure you get credit for your work. And, if you want to get credit for the impact your CS team is having on revenue, then you need to make sure that your work is documented. Where’s the best place to document it? In the existing revenue-tracking systems within your organization.
For example, when one of the sales reps at Drata reaches out to a Solutions Architect on Conor’s team via Slack for a consult on an opportunity, that chat is formally logged against that opportunity.
“I can take that logged activity and now equate it to an outcome,” says Conor. “Did that deal close? If it did, did it close at a higher ARR than the deals where we don’t have our solutions architects involved?”
Speak the language of revenue
“Sometimes, CS leaders and revenue leaders are like two ships passing in the night with their verbiage, their terminology, the metrics they speak about,” Conor points out. “If you’re a CS leader, and you live in the world of CSAT and NPS and customer health, then great — now equate those narratives to revenue.”
How does your NPS equate to retention? How does it tie into pipeline generation? Do you close expansion deals faster in healthy accounts? Is your average sales price higher if your customer has a higher health score?
With every word you say as a leader, you’re educating your team (and anyone else in the organization who’s listening) to think in terms of revenue enablement — not just sales enablement.
Make your Sales team jealous with these 4 skills
Like salespeople, your CS team should be constantly upskilling. The role of the CSM has changed dramatically, says Conor. You’re no longer just there to “give a warm hug to a customer when they have a problem.”
This isn’t about handing CS over to salespeople; it’s about making sure your CSMs have the skills to lead commercial conversations with customers just as effectively as your sales teams.
“I’m expecting my CSMs to be able to run a CSQL process,” Conor told us.
Here are five of the top skills you should be developing in your CSMs:
Outstanding discovery skills
Great CSMs know how to ask someone the same question 18 different ways to get to the root cause of the problem. They need to master the MEDDIC sales methodology, so they can apply it to renewal and expansion conversations. What are the metrics the customer is looking at when they’re making a renewal decision? Who’s the economic buyer? How many people are involved in the renewal committee?
A clear grasp on buyer personas
Customer Success needs to have the same handle on buyer personas that Sales does, and then build multi-threaded relationships with those different personas. Without this understanding, you won’t be building relationships with the real decision-makers, and you can kiss your renewals goodbye.
To quote Conor, today’s CSMs need to be able to distinguish between “critical contacts” (your buyer champions, influencers, and users) and “strategic contacts” (the key decision makers, the executive buyer, your executive sponsor).
Again, this will come down to stealing from Sales and training your CSMs to ask the right discovery questions to push for the right contacts.
The ability to say no and back it up with why
No, the customer is not always right. CSMs need to take on the “challenger” mentality that good salespeople have nailed. They should be a strategic business partner, who knows how to say no more than they say yes.
Their job isn’t to “make the customer happy.” It’s to challenge the customer to think in a better way to get the outcome they really want.
A commercial mindset
Your CSMs may or may not own the full commercial responsibility for the renewal or the expansion, says Conor, but they should always be thinking in terms of sales.
This looks like empowering CSMs to ask big, bold discovery questions like:
- Who is the ultimate sponsor of success for this project?
- Who is the individual who’ll be responsible for articulating a missed retention goal to the CEO?
“If a CSM hears something on a call that gives them an inkling that there's a path for growth in terms of our share of their wallet, I need CSMs to be able to bring some good context back to the account team and say, ‘Hey, I think we’ve got one on the line here.’”
Getting comfy with revenue is the key to CS confidence
We’re not suggesting that you should try and turn your CSMs into AEs; the jobs are different. CSMs own more accounts. They’re building a longer-term relationship. They have service targets and revenue goals.
But it’s time for CS teams, and more importantly CS leaders, to start focusing on their contribution to revenue. To do that, you’ll need to learn to speak the language of business.
You’ll also need to start applying the same level of rigor and discipline that you see in your Sales counterparts to your own leadership.
And you’ll need the kind of access to customer data that Sales teams take for granted.