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Why the Go-to-Market Number Two Has Become the Most Critical Hire in Private Equity-Backed Software
by Eric Walczykowski
On a recent episode of Tailored Talent, I sat down with Liz Moses, Partner in our Go-to-Market practice, to talk through what is happening in PE-backed software right now and what it means for the leadership builds we are running.
Liz spent several years working alongside CEOs in our CEO, Board and P&L practice before moving to go-to-market. She has watched the CEO profile shift in real time and understands how that shift cascades into what companies need at the CRO and CCO level.
The CEO Profile Has Changed, and Go-to-Market Is Feeling It
Something we have been tracking closely at Bespoke: the type of CEO being hired in PE-backed software has fundamentally changed. Historically, the pattern was a sales-oriented leader who climbed through go-to-market and assumed the top seat.
Today, the environment is different:
- There is significant tech debt across many platforms
- AI modernization is underway
- PE firms are increasingly selecting product-leaning CEOs to navigate that complexity
That is a smart call in a lot of situations, but it creates a very specific talent gap.
"The need for a go-to-market Number 2 has become utterly critical," Liz said.
Liz described how we are seeing real emergence of strong operational leaders who can own the full go-to-market stack and serve as the right hand to a product-leaning CEO.
If your CEO is heads down on tech debt and AI modernization, the person in that go-to-market seat is not a nice-to-have. That seat determines whether the growth thesis gets executed.
The Supply Problem Is Real
Liz described the market for proven go-to-market talent as being as tight as she has ever seen it. Deal flow is recovering and new platforms are forming, but executives grinding through existing holds are not ready to move. Demand is outpacing supply.
The more nuanced layer is where those leaders are going. The most proven CROs are being absorbed into operating partner roles and independent board seats across multiple portfolios. The full-time seat is simply harder to fill.
Liz advises clients to think differently about the first timer, the step-up GTM leader. At Bespoke, roughly 50 percent of our go-to-market C-suite placements are first-time leaders in the role. Searches that stay open to that profile close in around 93 days. Persistent pressure to find a proven name stretches that to 120. In a five-year hold, that gap is not trivial.
Supporting the Step-Up the Right Way
Getting a first-time leader into seat faster is one thing. Setting them up to succeed is another. Based on her experience, Liz explained that two elements matter most:
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1. Operating Partner Model
Go-to-market operating partners have expanded significantly across our top PE clients. For a step-up, having a seasoned operator one step removed as a sounding board is genuine risk mitigation, not oversight.
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2. Rev Ops
As Liz put it, moving from a strong sales leader into the CRO role makes the mandate considerably more operational. A high-quality rev ops leader who can build the infrastructure and align the teams is the difference between a step-up who flounders and one who delivers.
The CRO Role Is Evolving, Not Just the Candidate Pool
The CRO job itself has changed. The emphasis on new logo acquisition has given way to a sharper focus on NRR and GRR. As new logos became increasingly competitive in a tighter market, retention is where the points are now scored.
Around the $150-$200 million ARR threshold, it makes sense to separate the function. A chief sales officer focused on new logo acquisition, paired with a chief customer officer who is data-oriented, collaborative with product, and managing the feedback loop between customers and the road map. The companies that treat it as a distinct hire tend to build significantly stronger retention.
What This Means for Hiring
The PE talent thesis for go-to-market is being rewritten. The old model of finding the best salesperson and handing them the CRO seat is not sufficient anymore. The demand is for leaders who are operationally driven, data fluent, and genuinely collaborative across the organization.
The question is not just who has the longest track record. It is who has the right profile for the season you are in, supported by the right infrastructure to succeed from day one.
To learn more about Go-to-Market leadership trends, subscribe to the Tailored Talent podcast or connect with the Go-to-Market recruiting team at Bespoke Partners.
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