Since the first Chief Revenue Officers (CROs) started to emerge in the early 2000s as companies brought together revenue functions, the job description centered almost entirely on one thing: bookings. And that meant that pipeline, annual recurring revenue (ARR), and deal velocity ruled.
But that playbook doesn’t work anymore. The growth levers CROs have historically relied on are losing their pull as buying cycles grow longer, budgets tighten, and net-new business just isn’t enough on its own to move the needle. Let’s be honest — the old CRO move was basically sell fast, renew later. But in 2025, “later” comes knocking way sooner.
To keep growing, CROs are now being measured not just on how much new business they bring in, but how much they keep. And that’s pushed many CROs into a function they haven’t historically owned: customer success.
“Retention is a revenue strategy,” said Marilee Bear, CRO of Gainsight. “And in this environment, the companies that are going to win are the ones that can consistently prove value, protect their base, and then use the base to expand.”
Translation? Growth isn’t a funnel anymore, it’s a loop. The companies that get this are treating retention like it’s the new pipeline.
Sam Zayed, CRO of Xactly, sees the same shift, but also the extra scrutiny that comes with it. “Analysts on earnings calls now ask first about gross retention revenue (GRR) and net revenue retention (NRR),” he explained. “You start the year with a book of business—how’s that going to perform like-for-like? That’s GRR. Then, can you sell more and grow that base? That’s NRR.”
The challenge? Many CROs are inheriting CS organizations that aren’t built to support that kind of mandate. Sales and CS are misaligned, systems are fragmented, and everyone’s left doing backflips at the eleventh hour to save at-risk revenue.
Picture it: Everyone’s “pretty sure” they know who owns renewals until the customer submits a churn notice and suddenly everyone’s on a Slack channel pretending they were just about to flag the risk for executive attention.
In a recent webinar, Marilee and Sam sat down to look at what CS ownership really looks like—from building a 90-day plan to restructuring accountability, aligning compensation to retention outcomes, and integrating AI in ways that don’t replace teams, but help them protect their book of business.
Building a 90-day plan that works
For many Revenue leaders, suddenly owning CS can feel a lot like being dropped into the deep end of a pool. There’s new language, uncertainty, unfamiliar metrics, and maybe even some teammates you’re meeting for the first time.
There’s also no time to coast. While the ideal scenario would give you a long runway to figure things out, reality rarely does. That’s why having a focused 90-day plan matters, and it’s exactly what Marilee had when she took on ownership of CS at Gainsight.
“It’s a simple 30-60-90 day plan,” she shared. “Diagnosing and aligning, creating shared goals, and then operationalizing. I came in with fresh eyes, listened more than I talked, and pulled the common themes into one source of truth.”
The 90-Day Playbook for CRO Success
Days 1-30: Diagnose and Align
The first month focuses on understanding the current state through customer calls, employee listening sessions, and data analysis. “I tried my best to listen more than I talked,” Marilee emphasized, noting how she used AI tools to identify common themes across different perspectives from sales, CS, and account management teams.
Days 31-60: Create Shared Goals and Data
The second month involves establishing a single source of truth for health scores and forecasting, resetting compensation plans to align behavior with strategy, and bringing CS into the decision-making process. A critical change Marilee implemented was making renewals quota-bearing, with account managers having 40% of their compensation tied to renewals.
Days 61-90: Operationalize CS Playbooks
The final month focuses on implementing AI-powered tools to distribute work efficiently, defining expansion workflows, and establishing a weekly operating cadence for accountability. Using solutions like Staircase AI, Gainsight now tracks effort scores, time spent on high-value activities, and team burnout indicators.
Sam’s advice on getting started? “Don’t wait. The best thing you can do in your first 90 days is roll up your sleeves and dive in. Apply the same rigor we expect on the sales side to renewals and CS.”
Now here’s where things get spicy. You can’t fix retention if your teams are secretly competing for credit. That’s not alignment, that’s revenue roulette.
Aligning comp and accountability for renewals
When teams are chasing different goals—Sales chasing bookings, CS focused on customer health, and so on—misalignment is inevitable. But when comp reflects what matters (retention), everyone starts marching to the same beat.
And that’s exactly what Marilee did at Gainsight. “Renewals became quota-bearing,” she shared. “We needed a commercial owner who holds the number, with CS supporting adoption and health. Today, about 40% of our Account Managers’ variable comp is tied to renewals.”
It’s not just flat compensation, either. She also layered in incentives to reward the right behavior:
- 2-3x accelerators for renewal quota attainment
- Bonuses for closing multi-year deals
That may look different at your company, and that’s ok. What matters most, according to Sam, is accountability. “Who’s singularly responsible for the forecast? At every level—account, portfolio, region—you need someone accountable, the same way reps are in sales.”
Unfortunately, that alignment isn’t automatic. “It’s not hard to design the plan once GRR is defined at the top. The harder part is selling the board and CFO on why comp needs to align around retention.”
Pro tip: Start by showing how inconsistent ownership creates missed forecasts, missed targets, and fire drills at renewal time. When comp supports accountability, teams start operating with much more predictability.
Avoiding surprises with AI
If you’re managing hundreds or even thousands of customers, especially across mid-market and long-tail segments, it’s nearly impossible for even the most experienced teams to stay ahead of every renewal risk. You can’t expect a CSM to catch every signal, respond to every shift in sentiment, or read between the lines of every conversation.
That’s where AI becomes essential.
“You want to look a year out,” said Marilee, “and dive below the surface to identify sentiment—whether that’s a customer disappointed, thrilled, or quietly shopping us in an RFP—so you can surface risks earlier.”
Because we’ve all been there: a customer looks fine on paper… until the surprise churn notice hits your inbox.
Sam pointed to sentiment detection as a key use case. “Historically, it was someone’s opinion we relied on,’” he said. “But AI gives us another lens across all interactions. It helps highlight blind spots and map the white space in relationships.”
That’s why both Gainsight and Xactly are using AI not to replace humans, but to focus them. “We’re layering human-led for strategic expertise, digital-led for lifecycle automation, and agent-led for segments we can’t cover today,” Marilee explained. “Blending all three unlocks a differentiated customer experience at scale.”
A new CRO mandate calls for a new reality
Let’s make one thing clear: Bookings still matter, but retention is now just as critical to hitting the number.
That means aligning teams around shared outcomes, designing comp plans that reinforce shared retention goals, building forecasts that look beyond the current quarter, and using AI to get ahead of risk.
In this new era of revenue leadership, the CROs who win will be the ones who ditch the old playbook, shift their focus, and realize the most reliable source of revenue is the kind that’s already in the door.
