The Private Equity Podcast, by Raw Selection

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Bill Bell, Fractional Chief Revenue Officer at Chief Outsiders, about building a repeatable sales engine that drives organic growth across private equity portfolio companies.
Bill explains why commercial due diligence is often far less rigorous than financial, legal, and operational diligence—and how this leads firms to underwrite ambitious growth plans against sales organisations that were never designed to deliver them. He shares why hiring more salespeople rarely fixes a broken system, what strong sales leadership looks like, and how documented processes, CRM governance, pipeline discipline, and structured onboarding create scalable performance.
The conversation also explores the risks of hiring competitors solely for their “black book”, the value of stage-gated sales processes in long-cycle industrial markets, and Bill’s experience growing a PE-backed North American business from $180 million to $325 million in revenue while more than doubling its EBIT margin.
Key Takeaways
• Diagnose the commercial engine before adding sales headcount.
• Assess whether sales managers are truly managing, coaching, and forecasting—not simply carrying major accounts.
• Build systems that make capable salespeople productive rather than relying on individual heroics.
• Use clear stage gates to qualify opportunities early and avoid wasting months on deals that will never close.
• Professionalising the leadership team and commercial function can unlock organic growth and support M&A integration.
Timestamps
00:00 – Introduction to Bill Bell and Chief Outsiders
00:52 – The biggest commercial mistake private equity firms make
02:17 – Why hiring more salespeople can increase cost, not revenue
02:46 – Diagnose, fix the infrastructure, then add capacity
03:17 – Four areas of commercial maturity to assess
04:46 – What makes an effective sales manager
07:03 – How manufacturing companies typically hire sales talent
08:00 – The danger of relying on a salesperson’s “black book”
08:56 – Building a sales system instead of hiring your way to growth
09:56 – Four foundations to establish before recruiting sales reps
11:24 – What a documented sales process should look like
11:53 – Using stage gates in an 18-month industrial sales cycle
13:43 – The hidden cost of pursuing customers who will not buy
15:40 – Bill’s biggest PE-backed growth success story
17:34 – Recommended books, masterclasses, and podcasts
18:58 – How to contact Bill
19:27 – Closing remarks
Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent. We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.
🔗 Connect with Alex Rawlings on LinkedIn https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection www.raw-selection.com

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Bobby Ocampo and Sheldon Lewis, co-founders and managing partners of Blueprint Equity.
Following the successful close of Blueprint Equity’s $333 million third fund, Bobby and Sheldon explain how the firm identifies and supports high-growth B2B software companies. They discuss Blueprint’s early growth investment strategy, its direct sourcing infrastructure and the role its six-person operations team plays in supporting portfolio companies.
The conversation also explores the impact of artificial intelligence on software valuations, underwriting and value creation. Bobby and Sheldon explain how Blueprint has integrated multiple AI tools across sourcing, deal evaluation, portfolio operations and internal workflows.
They also share why vertical software businesses with deeply embedded customer workflows may be better positioned to withstand AI disruption than lightweight horizontal software products.

Key Topics
Blueprint Equity’s early growth investment strategy
Raising a $333 million third fund
Investing in B2B vertical software businesses
Building a large direct sourcing function
Supporting founders with recruiting, go-to-market and RevOps
Using AI to identify, prioritise and track investment opportunities
Connecting multiple AI tools through an integrated technology stack
Underwriting software businesses in an uncertain market
Assessing founders in minority growth investments
Moving quickly without creating employee burnout

Timestamps
00:00 Introduction
00:28 Blueprint Equity and the successful Fund III raise
00:53 The firm’s early growth equity investment thesis
01:43 Building the team and operations function
02:50 Common mistakes made by investment firms
04:21 Underwriting software businesses in the AI era
06:33 How Blueprint structures its value creation team
07:41 Recruiting and institutionalising portfolio companies
08:35 RevOps, reporting and financial visibility
09:53 How Blueprint uses AI internally
10:37 AI-driven sourcing and opportunity prioritisation
11:06 Using proprietary data in underwriting
12:32 Blueprint’s AI technology stack
14:01 Building a genuine direct sourcing strategy
15:24 The resources required for proprietary origination
16:46 Less obvious investment signals
17:14 Assessing the entrepreneur behind the business
18:13 Vertical software and the threat of AI disruption
20:25 Creating a fast-moving culture without burnout
22:09 Recommended private equity news and content
23:34 How to connect with Blueprint Equity
Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent. We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.
🔗 Connect with Alex Rawlings on LinkedIn https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection www.raw-selection.com

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Paul Isaac, Managing Partner of Isaac Management LLC, about investing in lower-middle-market businesses through a permanent-capital model.
Paul explains why Isaac Management operates without a traditional fund, predetermined exits or outside investor pressure. He discusses the risks of overleveraging, the importance of understanding a company’s community and culture, and why higher interest rates have created a disconnect between buyer expectations and seller valuations.
The conversation also explores Paul’s journey from banking and private credit to launching his own investment firm, how buyers can build trust with founders, and why operational improvement and talent development often create more sustainable value than financial engineering or acquisition-led growth.

Key Takeaways
Why excessive leverage and weak market understanding can undermine an acquisition.
How permanent capital supports patient ownership and long-term decision-making.
Why lower-middle-market deal activity has slowed as financing costs have increased.
How transparent communication and flexible deal structures can build seller trust.
Why operations may offer a stronger value-creation opportunity than pricing or M&A.
The importance of retaining, developing and incentivising key employees.

Timestamps
00:00 Paul’s background and the launch of Isaac Management
01:27 A permanent-capital approach without a traditional PE fund
02:24 The biggest acquisition mistake: overleveraging
04:50 Deal trends across the lower middle market
06:46 The valuation gap between buyers and sellers
08:39 Tariffs, financing costs and portfolio-company pressure
11:05 Chief Outsiders
12:32 Building an investment firm without institutional backing
15:28 From the search-fund concept to permanent capital
16:56 Why long-term ownership resonates with business founders
19:48 Lessons from seller conversations and dealmaking
21:18 Equity rollovers, seller financing and deal preparation
23:08 The most effective lower-middle-market growth lever
25:03 Talent retention and the true cost of replacing employees
26:31 Employee ownership and long-term engagement
27:00 Paul’s recommended media and publications
27:58 How to contact Paul Isaac
Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent. We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.
🔗 Connect with Alex Rawlings on LinkedIn https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection www.raw-selection.com

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Russ Roenick, Co-Founder and Managing Partner at Transom Capital, about building a differentiated middle-market investment strategy around carve-outs, special situations and operational complexity.
Russ explains how launching Transom shortly before the global financial crisis shaped the firm’s highly hands-on approach. He outlines how Transom identifies businesses with strong underlying industry potential but significant operational challenges, then applies a disciplined value-creation model to improve performance.
The discussion covers Transom’s six core operational transformations: salesforce effectiveness, new product innovation, digital transformation, supply-chain improvement, cost reduction, and talent and culture.
Russ also shares how the firm structures its operations team, why former portfolio-company CEOs and CFOs can become highly effective operating partners, and how Transom is deploying AI across back-office and commercial functions.

Key Takeaways
Why operational and situational complexity can create attractive entry points.
How Transom approaches carve-outs as an opportunity rather than simply additional risk.
The importance of building repeatable operational capabilities instead of attempting every possible transformation.
Why operating teams should be involved from underwriting through execution.
How supply-chain improvements have generated substantial gross-margin expansion.
Where AI is currently delivering value across accounts payable, receivables, customer service, forecasting and sales.
Why portfolio companies need internal AI champions to drive adoption.
How leaders can stay informed without overpowering portfolio-company management teams.

Timestamps
00:00 Introduction to Russ Roenick and Transom Capital
00:30 Moving from McKinsey into Private Equity
01:26 Transom’s value-oriented investment strategy
01:55 Distressed investing versus operational value investing
03:16 Using operational and situational complexity
04:14 Carve-outs, lender situations and tail-end funds
05:14 Launching Transom during the global financial crisis
07:04 The importance of adapting while maintaining investment discipline
08:29 Why Transom specialised in carve-outs and special situations
10:58 Why many firms view carve-outs as excessive risk
12:54 Transom’s six operational transformation strategies
13:23 Salesforce transformation
14:17 New product innovation
14:45 Digital transformation and AI implementation
15:15 Supply-chain and gross-margin improvement
16:13 Cost reduction, talent and culture
17:37 Structuring the portfolio operations team
18:05 Recruiting former portfolio-company CEOs and CFOs
19:59 Transom’s approach to AI adoption
20:57 Applying AI across back-office functions
21:49 Creating internal AI champions
22:48 Common AI use cases across the portfolio
24:10 How Russ stays informed
25:31 Leadership, decision-making and knowing when to step back
25:57 How to contact Russ
Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent. We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.
🔗 Connect with Alex Rawlings on LinkedIn https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection www.raw-selection.com

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Daniel Pianko, Co-Founder of Achieve Partners, about Achieve’s talent-led investment strategy, its $465 million exit of Optimum, and how the firm reached top 5% performance for DPI in Cambridge Associates’ US buyout benchmark.
Daniel shares how Achieve Partners invests in businesses where the biggest growth constraint is access to trained talent. Rather than simply competing for experienced hires, Achieve builds apprenticeship-style programmes inside portfolio companies, creating new talent pipelines that drive revenue, margin expansion, retention, and differentiated value creation.
The conversation explores the relationship between private equity firms and operators, why data-driven decision-making matters, how Achieve partners with universities and underrepresented talent pools, and why doing good and generating alpha do not need to be in conflict.
Key Takeaways:
Private equity firms should empower operators to challenge assumptions with data.
Achieve invests where talent shortages can be solved through focused training.
Apprenticeships can increase capacity, margins, retention and scalability.
Optimum shows how training pathways can unlock healthcare IT growth.
Strong impact and strong returns can reinforce each other.
Timestamps:
00:03 – Introduction to Daniel Pianko and Achieve Partners
00:29 – Daniel’s career path and linking social impact with financial return
01:52 – The mistake PE firms and portfolio companies make in the boardroom
03:44 – How to avoid PE investors driving strategy without enough data
05:10 – Achieve’s unique strategy: investing where talent shortages constrain growth
06:38 – Building apprenticeship programmes to solve supply-demand talent gaps
07:08 – Daniel’s Goldman Sachs training experience and how it shaped Achieve’s model
08:25 – Rebuilding the talent pyramid in lower middle market companies
09:49 – Why Achieve focuses on business services, tech services, and healthcare services
11:12 – Building talent programmes at the portfolio company level
12:10 – Solving the gap between university education and first jobs
13:04 – Why companies should stop searching for “purple squirrels”
14:58 – Partnering with universities and building access to talent
16:44 – The Optimum exit: $465 million sale to Infosys
17:12 – Optimum’s healthcare IT thesis and value creation plan
19:00 – Building healthcare IT training pathways with universities and industry bodies
20:56 – Challenges in expanding Optimum beyond its historic core
22:24 – How Achieve reached top 5% DPI performance
22:50 – Why Achieve sells when the underwriting target is achieved
23:42 – How training programmes create a natural exit point
25:07 – Aligning impact with alpha creation
27:31 – Talent arbitrage, underrepresented communities, and overlooked graduates
29:40 – Why solving major social problems can create superior returns
30:08 – Daniel’s recommended podcasts, books, and shows
31:57 – How to contact Daniel Pianko
32:23 – Closing remarks
Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent. We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.
🔗 Connect with Alex Rawlings on LinkedIn https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection www.raw-selection.com