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Tailored Talent

Tailored Talent

Hosted by Bespoke Partners

BusinessInterviews guests

Episodes

4

Latest episode

Oct 2026

Language

EN-US

About the show

Bespoke's CEO Eric Walczykowski interviews PE industry leaders for the latest insights and trends shaping the private equity talent landscape. Join us for an engaging quick-hit discussion on: macro trends in private equity, economy outlook, leadership in challenging times, go-to-market strategies, compensation trends, Step-up candidates, and strategic hiring. Listen in on this quick-hit podcast to hear about their take on current market trends! Want to watch the full video episode? https://www.bespokepartners.com/tailored-talent-insights/ -- Learn more at bespokepartners.com

Listen to episodes

4 recent
October 27, 2026Episode 6812 min

The AI-Ready CFO: What Private Equity-Backed Software Needs Heading Into 2027

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/

September 29, 2026Episode 6712 min

The Strategic RevOps Leader: What Private Equity-Backed Software Is Actually Hiring For

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/

August 26, 2026Episode 6628 min

AI Is Not Killing Software: The Mid-Year Private Equity Reality Check

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/

August 17, 2026Episode 6521 min

The Founder Transition: Finding the Right Next CEO

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/

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