A CRO is often rebuilding the GTM engine while simultaneously keeping the existing one running, essentially fixing the airplane while it’s in flight.
August 19, 2026
AI is changing the economics of software by making it easier and faster to build. As features that once created meaningful differentiation become easier to replicate, product differentiation doesn’t just disappear. It becomes more fragile as conventional sources of differentiation become less durable.
When that happens, the ability to consistently find the right customers, create demand, win business, and turn that process into a repeatable commercial engine becomes mission critical for any revenue organization. Put another way, as the product moat shrinks, the go-to-market moat becomes the only thing protecting the castle. This shift puts the Chief Revenue Officer front and center in terms of value creation.
Over the last decade, the CRO role has evolved beyond managing sales teams. In many companies, the CRO is now tasked with serving as a general manager for the commercial organization. This transforming role involves everything from rethinking the ideal customer profile to reshaping the GTM model, aligning marketing and sales efforts, fixing sales incentives, improving execution, and building a scalable revenue system.
Behind this evolving position, there’s a fundamental tension that’s easy to overlook. CROs have to transform commercial organizations while their efforts are judged on what those same organizations produce in the current quarter.
That’s where the two clocks come in.
Warren Zenna, the founder of The CRO Collective, has described this as a “Two Clocks” problem. The tension is between the time required to transform a commercial organization and the much shorter timeframe in which CEOs and board members expect measurable revenue results.
This framework resonated with me because I’ve seen it happen firsthand.
Meaningful commercial transformation takes time. It can often take anywhere from a year to eighteen months to fully understand what’s broken and make the required organizational changes to produce reliable results. In any significant GTM transformation, the CRO may need to:
None of that happens overnight, which most people understand. But the challenge is that the board operates in real time.
While these larger architectural changes are underway, there’s still a target number to hit. In the midst of pipeline reviews, forecast calls, and QBRs, someone will inevitably ask, “Is it working yet?” Here’s where the honeymoon can end quickly.
The CRO is rebuilding the commercial engine while simultaneously keeping the existing one running, essentially fixing the airplane while it’s in flight. I’ve seen this create a very predictable pattern.
The CRO identifies problems and proposes changes. The organization pushes back, which slows the rate of change. This results in missed quarterly quotas, and nothing makes a board member more anxious than the silence of an impending “miss.”
Suddenly, the CRO is spending more time explaining why the transformation needs more time than actually doing the transformation. The most frustrating aspect of this phenomenon is that none of this is particularly mysterious. The problem comes from expecting a single clock to measure two timelines.
Organizational resistance isn’t usually nefarious by itself. But change is scary. People protect what they know—their teams, their relationships, and the comfortable familiarity of business as usual. I’ve seen CRO searches where everyone agreed they needed a new commercial leader, but there was no actual agreement on what that leader was being hired to change.
The board thinks they’re hiring someone to accelerate growth, while the CEO thinks they’re hiring someone to fix Sales. Marketing thinks they’re getting a new partner, and the existing sales team thinks they’re getting a new boss. None of those views are necessarily wrong; however, those are often four very different jobs.
A failed CRO cycle is expensive and painful. It can easily reach $1.5–$4M, depending on company size, executive compensation, revenue scale, and how long the organization is operating without effective commercial leadership. For a PE-backed company, there’s another dimension to the problem.
Time.
The financial sponsor may have a defined value-creation plan and a limited window in which to execute it. Losing a year or more because the commercial leadership transition didn’t work out isn’t something that can be recovered later.
Here’s where the two-clock concept becomes particularly useful—if you lean into it and run two scorecards instead of one giant dashboard with 37 KPIs that nobody looks at after the first month.
These are the metrics that can tell you whether the business is delivering in the moment:
These numbers are what the CEO and board should hold the organization accountable for, full stop.
If you’re also rebuilding the commercial engine in parallel, you also need to know whether the things you’re changing are actually taking hold.
Some measures that tell you whether the commercial system is transforming include:
| Initiative | Leading Indicator |
| Vertical GTM | % of opportunities in target industries |
| AE Specialization | Win rate by vertical |
| Outbound | Meetings from ICP accounts |
| Marketing Changes | Qualified pipeline per campaign |
| Partner Strategy | Partner-influenced pipeline |
| MEDDPICC | % of opportunities with complete qualification |
| AI-Enabled Selling | Adoption and productivity improvement |
These leading indicators won’t replace your core, in-the-moment metrics, and shouldn’t. They give you something revenue metrics can’t, which is an early read on whether the changes you’re making are likely to produce better results down the road. The goal is to create a connection between what you’re changing today and the revenue transformation you expect to see tomorrow. It’s a straightforward objective but requires non-trivial execution.
Before hiring a CRO, I’d want the CEO and Board to be able to answer five questions.
Don’t start with the job description; start with the problem facing the business. SMART goals are important here—specific, measurable, achievable, relevant, and time-bound. “Move beyond founder-led sales” is fine for a vibe, but insufficient by itself as a directive.
Be specific about the commercial system, not just the revenue target. “We need more predictable revenue attainment” isn’t nearly granular enough. What, specifically, is preventing predictability?
A CRO can’t transform an organization if every significant change is off limits. Are there any sacred cows? If there are, that’s fine. Just call them out so your new CRO doesn’t end up in a surprise bullfight.
Separate today’s operating results from tomorrow’s transformation results by creating two paths with corresponding KPIs (leading and lagging). Otherwise, you’re going to spend the first six months arguing about whether the CRO is succeeding.
Change is disruptive. It’s critical to evaluate the organization’s cultural capacity to evolve. If the organization is deeply resistant to change, it’s better to know that—and acknowledge it—before hiring someone. Consider a more project-based or fractional approach to compartmentalize some of the changes ahead of the new CRO hire.
The Two Clocks and the paradox they create are real. The board can’t stop caring about the quarterly number just because the company is undertaking a GTM transformation. Likewise, a CRO can’t build a new commercial engine by ignoring the current business.
The solution is to manage these two clocks explicitly. Hold the organization accountable for today’s results while forecasting whether today’s changes are building a better commercial engine for quarters/years to come.
This approach may sound deceptively simple, but it’s non-trivial to implement. It requires the CEO, CRO, and board to agree upfront on what’s being transformed, what success looks like, what can and can’t be changed, and how progress will be measured. That’s what commercial readiness is really about.
As AI continues to compress product differentiation, companies that can build a defensible, predictable GTM motion will have an increasingly invaluable advantage. Modern CROs, with the right near-term and long-term frameworks, can help deliver this promise of increased enterprise value.
Does this story sound familiar? You can reach us at mastery@maestrogroup.co to learn more about how we’ve helped organizations with GTM transformation.
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