Tailored Talent

Hosted by Bespoke Partners

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Latest episode

Jun 2026

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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

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6 recent

June 10, 2026Episode 6312 min

Winning the War for Talent: The Modern Industrial Leadership Playbook for Private Equity-Backed Companies

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/

May 29, 2026Episode 6214 min

From Support Function to Value Driver: The New CHRO in PE-Backed Companies

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/

May 14, 2026Episode 6126 min

Finding AI-Adept CEOs: What Sponsors Need to Know

“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/

April 22, 2026Episode 609 min

More Than a Closer: The GTM Standard Private Equity Boards Hold To in 2026 | Tailored Talent with Andrew Reynolds

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 --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/

April 8, 2026Episode 5911 min

Talent and Value Creation: The CEO's Executive Team Decisions

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 1Watch Part 2Get 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/

April 1, 2026Episode 5813 min

The CEO's Private Equity Playbook: Leading a Sponsor-Backed Company

Most CEOs stepping into a PE-backed role for the first time underestimate how much of the job is about alignment before the work begins. The deal model, the sponsor relationship, the board you build around yourself. Getting that right before the company is running is what separates a smooth hold from one that becomes a constant negotiation. In Part 1 of this Tailored Talent conversation, Bespoke Partners CEO Eric Walczykowski sits down with Patrick Dennis, CEO of Avaya, former CEO of Venafi and a multi-exit software operator, to talk through how he approaches a new PE-backed role from the moment he says yes. Topics include: Why the deal model is true north and what it means if a sponsor will not share it How to pressure-test the deal thesis before day one through outside-in research The three dimensions of push and pull: financial, operational, and governance Why clear boundary conditions on executive hiring matter more than most CEOs realize The case for smaller, faster boards in PE-backed software How to match independent directors to the highest-complexity elements of the value creation plan Watch Part 1: https://www.linkedin.com/events/7442188475292102657?viewAsMember=true 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/