Tailored Talent

The CFO market in 2026 is running a paradox. Turnover is trending down, but the market is more constrained than ever. At Bespoke Partners, our Finance Practice is tracking a record year, up 50 to 60 percent year over year, while simultaneously watching the total market tighten around us. The reason is structural. When hold periods extend and sponsors need to protect a potential exit, the instinct is to lock in strong finance leadership rather than risk a transition. That keeps proven CFOs in seat, which compresses supply for everyone searching.

Into that constraint, two responses have emerged. The first is compensation creativity: sponsors are re-cutting equity structures, adding guarantees, and re-valuating strike prices to motivate executives who signed up for a four-year timeline and are now entering year six or seven. The second is the step-up hire. When a proven CFO elects not to take another turn, sponsors are pulling talent upward through what Katelyn Quaresma calls a vacuum effect: lower middle market CFOs stepping into middle market seats, middle market leaders stepping into flagship buyout roles. It is a creative and necessary response to a constrained pipeline.

Planning season accelerates this dynamic. The process of building a 2027 budget exposes gaps in finance leadership, both at the CFO level and in the VP Finance and controller layer below. We consistently see an uptick in search activity coming out of planning season, and 2027 will be no different.

The new variable is AI. Sponsors are no longer treating AI fluency as a bonus. It is now part of the CFO mandate and it operates on two tracks. The first is internal: what is the CFO doing to drive process efficiency across people, systems, and workflows to pull through to EBITDA margin? The second is external: how is the CFO partnering with product and go-to-market to build, price, and scale AI-driven revenue? Bespoke has now completed approximately 133 AI-forward mandate searches across the C-suite, and what we are seeing in finance mirrors what we see everywhere else. Curiosity and a demonstrated point of view on AI matter as much as technical depth. Sponsors are not looking for AI engineers. They are looking for CFOs who have engaged with the tools, iterated on what works, and can lead the internal conversation with conviction.

For sponsors heading into 2027, the question is binary. Do you have the right CFO to get to exit? And is that CFO AI ready? Our role at Bespoke is to help sponsors answer both questions with precision.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

Revenue operations has quietly become one of the most important hires in a private equity-backed software company. Not because it has always been strategic, but because the demands placed on it have fundamentally changed.

New pricing strategies. AI product releases. Tech stack transformation. Demand generation rethinking. The RevOps leader who can only manage forecasting and Salesforce hygiene is no longer sufficient for what growth-stage PE-backed software companies need to accomplish.

In this episode of Tailored Talent, Bespoke Partners CEO Eric Walczykowski sits down with Andrew Reynolds, Partner in our Go-to-Market practice, for a direct conversation on the evolution of RevOps and what private equity sponsors, CROs, and CEOs need to understand about hiring for the function today.

Andrew covers where RevOps should report and why the answer matters for how strategic the function can become, how to structure the interview process including the often-overlooked role of the investor in assessing candidates, what separates genuine AI fluency from AI enthusiasm in RevOps candidates, how to evaluate step-up candidates when the been-there-done-that pool is thin, how AI is compressing RevOps transformation timelines from quarters to weeks, and why the right RevOps leader may not have a RevOps title today.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

Every technology cycle produces the same panic. Client server was going to kill software. SaaS was going to kill software. Now AI is going to kill software. It has not happened yet, and it is not going to happen the way the headlines suggest.

In this mid-year Tailored Talent episode, Bespoke Partners CEO Eric Walczykowski and Chief Commercial Officer Adam Boone take stock of what the first half of 2026 looked like across private equity-backed software. They cover why AI is accelerating software rather than ending it, how private equity firms are getting AI wrong by confusing basic tool enablement with genuine transformation, and what the McKinsey three-horizon AI maturity model reveals about where most companies are stuck.

The conversation also covers the AI assessment work Bespoke has been doing for over two years, including a 50-plus question guide for sponsors pressure-testing executive AI readiness, why the go-to-market and finance functions are emerging as the highest-ROI areas for AI deployment, and why a slow executive search in today's market is not a recruiting inconvenience but a value creation problem with a calculable cost.

Bespoke's own book of business is up 60 percent year over year against an industry average of 11 percent. The firm has now placed over 200 executives with a primary AI mandate. This is the mid-year conversation grounded in that data. 

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

At the $30 to $50 million revenue stage in PE-backed software, every component of the business matters, and nothing is more consequential than getting the leadership transition right. In the vast majority of these deals, a founder is still in the business when the new CEO arrives. How that transition is structured, how the board is designed to support it, and how the right candidate is found and closed in a competitive market are questions that require a level of nuance most search processes do not deliver.

In this episode of Tailored Talent, Bespoke Partners CEO Eric Walczykowski sits down with Jenny Gray, Partner in our CEO, Board and P&L Practice, for a candid conversation on the growth CEO search. Jenny covers how she guides investors and boards through determining the founder's role before the search begins, what the first 90 days looks like for a successful second CEO, how she assesses first-time CEO candidates when multi-time operators are not available, and why the selling and relationship-building aspect of the search is now one of the most important factors in closing top candidates.

The conversation also covers AI readiness as a non-negotiable screening criterion, the growing role of board composition in supporting the growth CEO, and what it looks like when a president with P&L responsibility is brought in as a succession plan to the founder.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

The SaaS landscape is not experiencing a disruption. It is experiencing a reset. AI is compressing software development cycles, elevating product as the primary bottleneck in PE-backed software companies and forcing a fundamental rethink of what product and technology leadership needs to look like going forward.

In this episode of Tailored Talent, Bespoke Partners CEO Eric Walczykowski sits down with Haley Mundy, Partner and Product and Technology Practice Expert, and Ryan Bonner, Partner and Product and Technology Practice Expert, for a direct conversation on how AI is reshaping the P&T leadership mandate and what PE-backed software companies need to do differently in how they source, assess, and close the right leaders.

The conversation covers why the chief AI officer is a transitional role that works itself out of a job if done correctly, how the convergence of product and software development is changing the relationship between the CPO and CTO, why the best product and technology candidates today are rejecting high compensation packages in favor of the right problem to solve, and what it means to hire for potential rather than track record when the AI learning curve is measured in months, not years.

This is not a theoretical conversation about AI strategy. It is a ground-level view from the practitioners running more product and technology searches in PE-backed software than anyone else in the market.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

The industrial sector is modernizing faster than most private equity-backed companies are prepared for. The command-and-control operator who worked a decade ago is giving way to a different kind of leader: someone who can drive efficiency through data and automation, bring teams along through transformation, and think clearly about AI even when the roadmap is not fully drawn.

In this episode of Tailored Talent, Bespoke Partners CEO Eric Walczykowski sits down with Heather Kivett and Jared Moriarty, Partners at Industra Talent Partners, to talk through what is happening in the industrial talent market right now and what PE-backed companies need to do to find, attract, and retain the leaders who can execute in this environment.

Topics include the push toward visibility, efficiency, and labor productivity as the core modernization agenda; why leadership style has become as important as operational experience in industrial searches; how compensation packages need to evolve in longer hold periods; how AI is showing up in industrial businesses and how Industra is screening for it; and what separates the PE firms that consistently build winning industrial leadership teams from those that do not.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

The CHRO role in private equity-backed companies is not what it was five years ago.

People costs are among the largest line items on any P&L. AI is forcing every organization to rethink how work gets done. And the sponsors who are treating HR as a tactical support function are falling behind the ones who have put a strategic people leader at the center of their value creation plan.

In this episode of Tailored Talent, Bespoke Partners CEO Eric Walczykowski sits down with Dani Pfeiffer, Partner and leader of Bespoke's Human Capital Practice, to talk through what the modern CHRO looks like in PE-backed companies, how AI is reshaping the people leader's mandate, and what it takes to find and place a people leader who can actually drive enterprise value.

Topics include why the CHRO needs to be a peer to the CFO rather than a report to one, how AI adoption and workforce redesign have become core to the people leader's job, what execution-oriented HR leadership looks like in lean PE environments, and why this role is not one sponsors can afford to wait on.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

“If you are thinking about changing your CEO, act on it sooner rather than later.”

The SaaS landscape is shifting faster than most private equity -backed software companies can adapt.

AI is reshaping every product roadmap, every go-to-market motion, and every leadership expectation. The CEO who worked five years ago may not be the CEO who creates value today.

In this Tailored Talent panel discussion, Bespoke Partners CEO Eric Walczykowski brings together the firm's CEO, Board and P&L practice leaders for a candid conversation on what is changing in the executive market and how the best sponsors are responding.

Katherine Baker, Partner and CEO Practice Lead, Jenny Gray, Partner and CEO Practice Expert, and Alex Bossetta, Partner and CEO Practice Expert, cover the full landscape: the rise of the product-leaning CEO, how AI fluency is being assessed when there are no 30-year resumes to lean on, why there are roughly 100 executives in the world who have run a software company above 500 million in revenue, and what sponsors need to do differently to land the right leader in a market where the best candidates are fielding 20 to 30 calls in the first two weeks after a deal is announced.

This is the conversation happening inside the most active CEO search practice in private equity-backed software. Bespoke Partners has placed more CEOs in PE-backed software than any other firm in the world. What the team shares here reflects what they are seeing on the ground every day.

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

The best salesperson at the helm is no longer enough. Private equity boards have raised the bar, shifted the metrics they scrutinize, and raised their expectations of what a go-to-market leader needs to deliver. The leaders who are winning in PE-backed software in 2026 look different from the ones who won five years ago.  

In this episode of Tailored Talent, Bespoke Partners CEO Eric Walczykowski sits down with Andrew Reynolds, Partner in our Go-to-Market practice, to break down exactly what Private equity boards are demanding and what the winning go-to-market profile looks like.  

Topics covered: 

- How PE board scrutiny has shifted from ARR growth to profitability metrics: LTV to CAC, CAC payback, and sales efficiency ratios 

- Why the go-to-market scorecard leads with metrics: what candidates inherited, what they moved it to, and how they did it 

- How backchannel validation and AI tool usage reveal whether a candidate can deliver versus just talk about it

- The multi-playbook athleticism PE-backed platforms are looking for and where that model breaks down at scale 

- The $250M ARR inflection point where the go-to-market structure needs to consolidate under one leader 

- Why end market experience is non-negotiable in complex verticals and what six months of ramp costs in a five-year hold 

- How compensation structure is shifting: EBITDA-oriented bonuses replacing bookings targets, and deeper equity diligence from candidates 

- The three go-to-market leader attributes that will define the difference-makers in 2026  

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Tailored Talent is the Bespoke Partners vodcast featuring candid conversations on the talent decisions shaping private equity-backed software and technology companies.  Bespoke Partners is the leading executive search firm for PE-backed software and SaaS companies, with functional specialization across CEO and Board, Go-to-Market, Product and Technology, Finance, and HR and People practices.  

Learn more: https://www.bespokepartners.com  

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/

The most consequential decisions in a PE hold are not the ones made in the boardroom. They are the ones made about people.  Which executives to bring in, when to make changes, how to build the right measurement infrastructure before you hire the revenue leader, and why the CFO search is structurally harder than most people will admit.  

In Part 2 of this Tailored Talent conversation, Bespoke Partners CEO Eric Walczykowski continues his discussion with Patrick Dennis, CEO of Avaya, former CEO of Venafi, shifting to the executive team decisions that determine whether a value creation plan actually gets executed.  

Topics include: 

• Why Patrick hires to the season, not the destination, and what the special forces executive model looks like in practice 
• The cascade effect of a CRO change and why a year of rebuild is 20 to 25 percent of a five-year hold 
• Why revenue operations should be built before the CRO is placed 
• What Patrick wants from a CRO: forecast accuracy, consistency, and transparency, not just growth 
• The structural tension that makes the CFO search the hardest in PE-backed software  

Watch Part 1

Watch Part 2

Get deeper insights by downloading your version of our newest release of the Private Equity Talent Report, Talent Market Update: https://www.bespokepartners.com/private-equity-talent-report/