Tailored Talent

Hosted by Bespoke Partners

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Latest episode

Aug 2026

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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

3 recent

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/

July 13, 2026Episode 6421 min

The AI Adept Leader: How PE-Backed Software Is Rethinking Product and Technology Hiring

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/