In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jason Pearsall, CEO of Club Caddie Holdings, about his evolution from startup founder to a private equity-backed business leader. Jason shares his lessons from two successful exits, the pivotal shifts in his golf technology business, and the art of balancing data with instinct. Jason shares his perspective on the importance of defining your ideal customer profile and the value of due diligence for sustainable growth. He also highlights why success isn’t always about chasing VC funding but about finding partners aligned with long-term goals while transforming traditional industries with technology.

What you will learn:

• How to identify and pivot when your initial business model isn't meeting market needs
• The critical importance of defining your Ideal Customer Profile (ICP) before scaling
• Why tracking specific KPIs and financial metrics is essential for successful acquisitions
• How to balance founder vision with investor expectations when choosing funding partners
• Differences between managing a startup versus a private equity-backed company
• Why is integrating operational and financial systems is crucial for business scalability
• How to transform traditional businesses through technology 
• The essential metrics for running a successful golf course operation

Jeff Pearsall is the CEO and co-founder of Club Caddie Holdings, a comprehensive golf course management software solution. With a background in corporate law and deep roots in the golf industry, Jeff has successfully grown and exited multiple businesses, including leading two golf course acquisitions and achieving a notable exit to Constellation Software. His journey from founding Golfler, an early golf-tech startup, to building Club Caddie into a market leader demonstrates his expertise in scaling technology companies and optimizing golf course operations.

Episode Resources:

• Jason Pearsall on LinkedIn
• Club Caddie Holdings Inc Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook: Transforming Accounting Solutions

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Gabe Lullo, CEO of Alleyoop, to explore his journey from SDR to CEO and the lessons learned while scaling a 150-person revenue-on-demand company. Gabe shares insights on balancing rapid growth with financial discipline, diversifying client portfolios, and building scalable systems without compromising quality. He also reveals why investing 15–20% of revenue in sales and marketing can drive sustainable success and how leveraging content over cold calls builds trust and accelerates sales cycles. A must-listen for entrepreneurs scaling service businesses.

What you will learn:

• How to build mental resilience in sales by categorizing objections into 10 core buckets 
• Why does it take 90 days to properly establish sales development campaigns 
• How to balance aggressive growth with financial sustainability 
• The framework for diversifying client portfolios: maintaining 40% enterprise and 60% SMB clients for stability
• Why organic content marketing is replacing traditional sales collateral
• Implement the "democratic leadership" approach when driving organizational change
• The 15-20% revenue guideline for sales and marketing spend 
• Why leveraging content over cold calls can accelerate sales cycles
• How to transition from an individual contributor to a leader by shifting focus 

Gabe Lullo is the CEO of Alleyoop, a revenue-on-demand partner helping brands like Adobe, Bevy, and ZoomInfo scale with confidence. Rising from SDR to CEO, Gabe has built deep expertise in enterprise software sales, people operations, and revenue generation. At Alleyoop, he has grown the team to 150+ employees while pioneering scalable, content-driven sales strategies. As host of the Do Hard Things podcast, Gabe shares insights on sustainable growth, client partnerships, and building resilient, high-performing sales organizations.

Episode Resources:

• Gabe Lullo on LinkedIn
• Alleyoop Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook: Transforming Accounting Solutions
  
  
  

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon

Is your finance department your company’s biggest security risk?

Join Jeff Rudner on this episode of 5 to 50: Financial Strategies for Growing Companies as he welcomes Chithra Rajagopalan, Head of Finance at Obsidian Security, to discuss how the convergence of finance and cybersecurity can either expose companies to billion-dollar breaches or unlock strategic resilience. From managing phishing threats to balancing AI innovation with secure financial practices, Chithra shares practical, cost-effective tactics for protecting sensitive data and strengthening internal operations. Whether you're a founder, CFO, or finance leader, this episode is packed with insights to help you scale securely in today’s digital-first world.

What you will learn:

• How to quantify cybersecurity risks and their potential financial impact 
• Why separating finance and security departments is crucial for maintaining expertise
• The critical importance of proper user access management 
• How to implement cost-effective security measures for early-stage companies 
• Why multi-factor authentication and proper data hygiene are non-negotiable 
• How to balance AI adoption in finance while maintaining security and data protection
• The framework for creating effective partnerships between CFOs and CISOs
• Why centralized data management must be balanced against security considerations
• How to protect against increasingly sophisticated phishing attacks 
• The essential security protocols every finance department should implement

Chithra Rajagopalan is a seasoned finance leader with deep experience in high-growth SaaS companies. Currently Head of Finance at Obsidian Security, she has successfully led organizations through fundraises, acquisitions, international expansion, and IPO readiness. With prior roles at Deloitte and fast-paced startups, she’s known for her strategic insight, operational rigor, and strong executive partnership. Chithra also serves on the boards of two non-profits focused on nurse retention and social equity for underprivileged children, reflecting her commitment to impact beyond business.

• Chithra Rajagopalan on LinkedIn
• Obsidian Security Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook Transforming Accounting Solutions

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon

Looking to scale your service-based business without drowning in operational chaos?

Join Jeff Rudner on this episode of 5 to 50: Financial Strategies for Growing Companies as he sits down with Alan Pentz, founder and former CEO of Corner Alliance, to unpack how he scaled a consulting firm from startup to $35M in revenue. Alan shares actionable insights on evolving beyond founder-led sales, setting financial benchmarks like labor efficiency and gross margins, and making tough calls about leadership and systems. Tune in to learn how to work on your business, not just in it, and build a company that thrives without you.

What you will learn:

• How to evolve from founder-led sales to building a scalable sales organization
• Why gross margins must exceed 40% to create a sustainable business
• The critical financial metrics for tracking service business health
• How to strategically build your leadership team as you scale from $2M to $35M 
• Why proper financial systems and projections are essential before scaling past $5M
• The framework for transitioning from working in the business to working on it
• How to identify when loyal early employees are blocking company growth
• The optimal timing for implementing new systems and processes 
• Why equity compensation rarely makes sense in privately held service businesses 
• How to achieve owner independence while maintaining strategic control 

Alan Pentz is the founder and former CEO of Corner Alliance, a firm dedicated to enhancing digital infrastructure for federal programs in areas including broadband, cybersecurity, and public safety. With over two decades of consulting experience across government and corporate sectors, Alan has developed significant expertise in organizational transformation and business scaling strategies. Through his latest venture, His practical approach to business growth is based on learnings from scaling Corner Alliance to $35 million in revenue.

• Alan Pentz on LinkedIn
• Corner Alliance Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook Transforming Accounting Solutions

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon

What’s the smartest way to manage cash when the market is uncertain?

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Joy Mbanugo, CFO of CXAI and a former executive at Google and BlackRock, to answer that and more. Joy shares actionable strategies for maximizing cash reserves. 

Navigating funding options and evolving your finance function as your company scales. She also unpacks how AI is revolutionizing financial operations and why finance should be a central pillar of business strategy. This episode is packed with valuable insights for founders and CFOs who are ready to lead with confidence.

What you will learn:

• How to strengthen your balance sheet by prioritizing cash during economic uncertainty 
• Why distinguishing between different types of cash is crucial for decision-making
• The strategic approach to scaling your finance function 
• How to position finance as a central function 
• Why EBITDA and other key metrics should be understood across the company
• How to leverage AI tools in finance operations
• The differences between debt and equity financing and how to choose the right funding strategy
• Why cash management should be a daily priority

Joy Mbanugo is the CFO of CXApp (NASDAQ: CXAI), where she leads financial strategy, capital allocation, and investor relations for the innovative SaaS company. With a background at Google, BlackRock, and EY, she brings deep expertise in public company finance, board governance, and scaling high-growth businesses. Joy excels at aligning financial operations with business strategy, driving transparency, and building investor confidence. A lawyer and accountant, she’s also an active investor and advocate for women-led ventures and equitable growth in the startup ecosystem.


Episode Resources:

• Joy Mbanugo on LinkedIn
• CXAI Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook Transforming Accounting Solutions
  
  

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon

How do you grow a luxury service business without sacrificing quality or cash flow?

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Kevin Diemar, CEO and President of Unity Jets and former Wall Street trader, to uncover how Kevin scaled a private jet brokerage using relationship-driven strategies and an asset-light model. He shares powerful lessons on maintaining high-touch service, hiring smart, and managing emotional highs and lows in business. Kevin also shares how he evaluates angel investments by focusing on authenticity and connection. Whether you're scaling a client-focused business or exploring private markets, this episode offers practical, real-world insights for building lasting success.

What you will learn:

• How to pivot from transactional to relationship-based models while maintaining profitability
• The "Never Too High, Never Too Low" principle for managing emotions 
• Why transparency and honesty are crucial for building long-term client relationships 
• How to scale a service business without compromising quality 
• The "Asset Light" strategy for growing a service business while maintaining cash flow
• How to identify and capitalize on market opportunities 
• Why letting successful ventures grow naturally is more effective than rapid scaling
• The framework for evaluating investment opportunities 
  
  

Kevin Diemar is the Founder of UnityJets, a global private jet brokerage built on a capital-light model and exceptional client service. A former Wall Street trader and VP of Sales at MarquisJet, Kevin brings deep expertise in high-stakes financial markets and luxury sales. He’s a seasoned CEO known for scaling relationship-driven businesses in private aviation. With strengths in negotiation, business planning, and entrepreneurship, Kevin has redefined what it means to grow a high-end service brand with integrity and precision.

• Kevin Diemar on LinkedIn
• UNity Jets Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook Transforming Accounting Solutions
  
  

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon

What if you could transform your finance team from simply reporting numbers to being strategic business partners in the organization's growth?

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Ali Firoozi, CFO of The Pac Group, to explore how finance leaders can drive business growth through strategic insight and tech adoption. Ali shares his journey from aspiring lawyer to CFO and explains how finance teams must evolve from number crunchers to business storytellers. They discuss best practices for implementing new systems, selecting impactful KPIs, managing fixed vs. variable costs, and embracing AI. Packed with real-world wisdom, this episode is a must-listen for any leader modernizing their finance function.

What you will learn:

• How numbers tell compelling business stories
• Why modern finance departments must evolve from reporting to becoming strategic business partners
•  The challenges and best practices of implementing new financial systems
• How to select and track meaningful KPIs that drive business success 
• The critical balance between fixed and variable costs in professional services firms
• The transformative impact of AI on financial operations and team productivity
  
  

Ali Firoozi is the Chief Financial Officer at The PAC Group, a global consulting and engineering firm. With over 20 years of experience in finance, Ali brings an entrepreneurial mindset and a proven ability to lead through growth and change. He specializes in financial strategy, forecasting, process design, and executive reporting. A former banking professional with degrees in International Business and Finance and an MBA, Ali excels at integrating finance with innovation to drive enterprise value and strategic partnerships.


Episode Resources:

• Ali Firoozi on LinkedIn
• The PAC Group Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook Transforming Accounting Solutions

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon

Finance's #1 bottleneck is reconciliation. What if you could revolutionize your financial operations with AI while maintaining complete control and transparency?

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with ex-Facebook director and CEO and co-founder of Ledge, Tal Kirschenbaum, to discuss how AI is transforming financial operations for businesses in the accelerated scaling phase. He draws on his experience at BCG, Facebook, and Melio, to share actionable strategies for automating reconciliation, improving financial reporting, and building trust in AI-driven systems. The conversation covers the shift from manual to continuous close processes, balancing growth with control, and maintaining transparency in an AI-powered future. This episode is a must-listen for finance leaders and founders aiming to scale smart while staying compliant.

What you will learn:

• How to transition from manual to automated financial processes
• Why progressive automation is key to successful AI adoption in finance teams
• The critical balance between growth and financial sustainability, when backed by VC
• How to build trust in AI-powered financial solutions 
• How to resolve reconciliation at companies on the growth path
• How to evolve from reactive accounting to continuous close processes 
• The importance of early technology investments 
• How to maintain founder mentality and accountability as your organization grows
  
  

Tal Kirschenbaum is the CEO and Co-founder of Ledge, an AI-powered platform revolutionizing financial operations for mid-market and enterprise companies. With an impressive background spanning roles at BCG, Facebook, and Melio, Tal brings deep finance, technology, and strategic operations expertise to his entrepreneurial ventures. Drawing from his experience at Melio, where he witnessed firsthand the challenges of high-volume financial reconciliation, Tal founded Ledge to address the growing complexity of financial operations through intelligent automation. His leadership has positioned Ledge as a pivotal solution for businesses seeking to enhance their financial processes, particularly in cash reconciliation and journal entry creation.

Episode Resources:

• Tal Kirschenbaum on LinkedIn
• Ledge Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook Transforming Accounting Solutions

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Alex Glueckler, VP of Accounting at CrossFit, to discuss how finance can evolve from a reactive function into a proactive, strategic partner. Alex shares insights on simplifying financial metrics, building cross-functional relationships, and creating a finance culture that supports, not stifles, growth. He emphasizes the importance of servant leadership, the balance sheet’s role in long-term sustainability, and the value of early embedding finance in strategic planning. Whether you’re scaling or optimizing, this episode delivers actionable strategies for financial leadership at every stage.

What you will learn:

• How to build a strategic finance function that enables growth 
• Why simplifying KPIs to 2-3 core metrics creates better alignment and decision-making
• The "Strategic No" framework for finance leaders to guide business decisions 
• How to embed finance throughout the organization by building relationships 
• Why understanding accounting and finance fundamentals is crucial for business scaling
• How to balance short-term cash management with long-term value creation
• How to develop servant leadership in finance to build a high-performing team 
• The critical role of the balance sheet in ensuring long-term business sustainability

Alex Glueckler is an accomplished finance executive with over 18 years of experience spanning accounting, operations, and strategic leadership, with more than a decade in private equity-backed companies from startup to IPO and exit. As VP of Accounting at CrossFit, LLC, he leads global accounting operations, ensuring financial transparency and compliance. Known for aligning financial strategy with business goals, Alex is passionate about building strong stakeholder relationships and driving growth that supports CrossFit’s mission to improve health, happiness, and performance.

Episode Resources:

• Alex Glueckler on LinkedIn
• CrossFit LLC Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook Transforming Accounting Solutions
  
  

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon

What if you could learn from someone who successfully scaled and sold a SaaS company in Europe before launching their next venture?

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Johan Hoernell, CEO and co-founder of Reveal Automation. Johan shares his journey from McKinsey consultant to successful SaaS entrepreneur, offering practical insights on scaling businesses, building transparent financial systems, and preparing for successful exits. He explains why empowering teams through context, rather than control, is vital for sustainable growth. Whether you're growing your first startup or leading a growth-stage SaaS company, Johan’s strategies around operational excellence, financial leadership, and entrepreneurial resilience provide invaluable lessons for building and exiting technology ventures.

What you will learn:

• Why transparent financial metrics and company-wide KPI visibility drive better results
• The "Context Over Control" leadership principle for empowering teams 
• How to build effective finance operations from bookkeeper to CFO 
• Why pre-acquisition preparation and financial hygiene are crucial for a smooth exit 
• The strategic framework for bootstrapping a new venture 
• How to identify the right moment to exit a business 
• The importance of focusing on core competencies and outsourcing critical functions 
  
  

Johan Hoernell is the CEO and Co-founder of Reveal Automation, specializing in the automation and enablement of enterprise digital tools. With a distinguished background including strategic consulting at McKinsey and successfully scaling Time Edit to acquisition, Johan brings deep expertise in technology optimization and business transformation. His entrepreneurial journey spans from early programming interests to executive leadership, where he successfully led Time Edit's expansion from a Nordic-focused company to a broader market presence.

Episode Resources:

• Johan Hoernell on LinkedIn
• Reveal Automation on LinkedIn
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook Transforming Accounting Solutions

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon