5 to 50: Financial Strategies for Growing Companies

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jeremy Klein, General Partner at super{set}, a groundbreaking AI startup studio. Jeremy's unconventional journey—from teaching beekeeping in rural Paraguay as a Peace Corps volunteer to advising hundreds of startups as a corporate attorney, to now co-founding data and AI companies—offers a masterclass in adaptability and strategic thinking. In this conversation, Jeremy shares invaluable insights on what separates successful founders from the rest, how to systematize financial operations across portfolio companies, the critical metrics that drive B2B SaaS growth, and how to implement AI strategically in your business. Whether you're a founder seeking to scale or a finance leader building systems for growth, this episode delivers actionable wisdom on vision, grit, and building companies that last.


Episode Chapters:


00:00 Intro: Meet Jeremy Klein - From Peace Corps to Venture Capital


02:10 From Beekeeping in Paraguay to Building Trust and Overcoming Fear


03:44 The Leap from Peace Corps to Law and Startups


05:00 What Sets Great Founders Apart: Vision and Product Strategy


08:25 The Trough of Sorrow: How Successful Founders Persevere


11:00 Asking for Help Isn't Giving Up - It's the Opposite


11:43 What Makes super{set} Different: Company Building vs Traditional VC


14:03 Systematizing Success: Financial Models and Back Office Foundation


18:00 The Right Metrics: What to Measure and When


22:00 Cascading Vision: Creating Customer-Centric Culture as You Scale


24:38 Information Sharing: Balancing Transparency with Team Readiness


27:00 AI Strategy for Entrepreneurs: Picking the Right Problems to Solve


30:18 Avoiding Shiny Object Syndrome in the Age of AI


33:08 Finding Market Opportunities: Known Problems vs New Problems


35:04 Life Advice: It's a Marathon, Not a Sprint


37:17 Rapid Fire: AI Trends, Book Recommendations, and Hiring Strategy


Episode Resources:


Guest:

• 
  Jeremy Klein on LinkedIn: https://linkedin.com/in/jeremy-s-klein/
• super{set} Website: https://superset.com
• Email: [email protected]
  
  

super{set} Company Information:

• 
  super{set} on LinkedIn: https://linkedin.com/company/superset-studio
• TechCrunch Coverage: https://techcrunch.com/2019/10/02/superset/
  
  

Books & Resources Mentioned:

• 
  The Qualified Sales Leader: Proven Lessons from a Five Time CRO by John McMahon: https://amazon.com/Qualified-Sales-Leader-Proven-Lessons/dp/0578895064
• The Boy, the Mole, the Fox and the Horse (referenced in conversation)
  
  

Host & Proseer:

• 
  Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH
• Proseer Website: https://proseer.co/
• Book a Consultation: https://proseer.co/contact/
• Download Our eBook - Transforming Accounting Solutions: https://proseer.co/rules-ebook/
  
  

Key Takeaways:


On Founder Success:

• 
  Vision: The best founders articulate audacious, compelling visions that inspire investors and teammates
• Product Strategy: Great founders see beyond the immediate and can articulate a clear path from today's product to tomorrow's platform
• Open-Mindedness: Successful founders ask the right questions, know what they need to know, and trust experts to execute
  
  

On Financial Systems:

• 
  Start with financial models from day one—even when you're "making it up"
• Models are vehicles for discussion and alignment across the entire team
• Track 3-5 key metrics initially: ARR, CAC, pipeline, close times, and eventually NDR and gross margins
• Create 3-year plans to test assumptions and avoid short-term thinking
• Implement CRM systems (like HubSpot) from the beginning to build data-driven muscles
  
  

On AI Implementation:

• 
  Pick problems humans can't solve well or don't want to solve
• Avoid core system replacements; focus on augmentation and specific pain points
• Good AI problems: QA testing, compliance, documentation, security questionnaires
• Focus on providing results, not just tools
• Recognize AI's limitations and design accordingly
  
  

On Scaling Culture:

• 
  Embed customer-centricity as a core value from day one ("blueberries and pancakes")
• Be selective about financial transparency—people aren't always equipped to process it
• Maintain biweekly executive meetings and monthly all-hands for alignment
• Hire strategically, even if it feels early—waiting too long costs more than acting early
  
  

About the Guest:


Jeremy Klein is a General Partner at super{set}, a startup studio that founds, funds, and builds AI and data-centric companies. Since super{set}'s inception in 2018, Jeremy has been instrumental in building a durable company-building machine across B2B SaaS, AI, and data management. The firm has founded over 20 companies and achieved its first major exit with Habu's $200 million acquisition in 2024. Prior to super{set}, Jeremy was a corporate attorney at Gunderson Dettmer, where he advised hundreds of technology startups and venture capital investors across all stages of growth. His unconventional background includes serving as a Peace Corps volunteer in rural Paraguay, where he taught beekeeping and learned invaluable lessons about trust, persuasion, and working with people—skills that continue to shape his approach to building companies today.


About 5 to 50 Podcast:


5 to 50: Financial Strategies for Growing Companies helps founders and finance leaders navigate the critical journey from $5M to $50M in revenue. Hosted by Jeff Rudner, each episode features conversations with successful entrepreneurs, CFOs, and investors who share practical strategies for scaling operations, managing cash, building finance functions, and implementing systems that support sustainable growth.



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, Jeff Rudner sits down with Brandon Spear, CEO of TreviPay, whose three-decade career spans four continents and multiple successful exits. Brandon shares his journey from co-founding South Africa's first commercial internet service provider in the early 1990s to leading TreviPay through its recent private equity carve-out. He offers candid insights on navigating the 2008 financial crisis, turning around struggling businesses through customer-centric approaches, and preparing companies for strategic acquisitions. Brandon also discusses the future of B2B payments, the role of AI in creating competitive moats, and why building trust is the most undervalued leadership skill. Whether you're a founder preparing for an exit or scaling through uncertainty, this episode is packed with battle-tested wisdom from someone who's been there multiple times.


Episode Chapters:


00:00 Intro: Meet Brandon Spear, CEO & Serial Entrepreneur


02:00 Early Risks & The Birth of the Internet in South Africa


06:00 Turning Around Quadrant Through Customer Feedback


12:00 Navigating the 2008 Financial Crisis: Cutting Fat vs. Muscle


17:00 Preparing for Exit: Selling to Ariba in 2011


21:00 Joining TreviPay: 11 Years of Growth and Evolution


25:00 Choosing the Right Private Equity Partner


27:00 The Future of B2B Payments: AI, Digitization & Stable Coins


36:00 Building Leadership Teams: Timing Executive Hires Right


43:00 Rapid Fire: Career Lessons, Books & Leadership Skills


Episode Resources:


Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH


Brandon Spear on LinkedIn: https://www.linkedin.com/in/brandon-spear-171a112/ 


TreviPay Website: https://trevipay.com


TreviPay on LinkedIn: https://linkedin.com/company/trevipay


Proseer Website: https://proseer.co/


Book a Consultation Contact Us: https://proseer.co/contact/


Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/


Book Mentioned:


The Innovator's Dilemma by Clayton M. Christensen - Available on Amazon: https://amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780



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 Jordan Feld, serial entrepreneur and founder of CoreGo, to explore the art of going from zero to one in business. Jordan shares his journey through multiple ventures—from real estate crowdfunding and private market investing to healthcare real estate—and the mindset shifts that shaped his success. He discusses how to test and validate ideas, build lean, raise capital, and know when it's time to sell. Packed with insights on focus, risk, and execution, this episode is a masterclass for entrepreneurs at any stage.


Episode Chapters:


00:00 Intro: Meet Jordan Feld, Serial Entrepreneur and Founder of CoreGo
02:00 Solving Personal Problems as a Path to Innovation
04:15 Building a Real Estate Crowdfunding Platform
06:00 Creating a Secondary Market for Private Investments
08:00 The Power of Testing Small and Validating Ideas
10:30 Avoiding Risk and Building Smart
13:00 Finding Product-Market Fit in Real Estate Investing
15:00 Laser Focus and the Entrepreneurial Mindset
18:00 Building the Right Team for Growth
21:00 Raising Capital and Communicating Value
25:00 Investing Your Own Money in Every Deal
28:00 Tracking Performance and Financial Discipline
30:00 Hard Lessons Learned from the Entrepreneurial Journey
33:00 Knowing When to Sell and Start Again
36:00 The Joy of Going from Zero to One
37:00 Jordan’s Recommended Books for Entrepreneurs
39:00 Life Motto: "No Excuses, Don’t Fail"
40:00 Closing Thoughts and Where to Find Jordan Feld


Episode Resources:


Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH
Jordan Feld on LinkedIn: linkedin.com/in/jordanfishfeld
CoreGo Website: https://www.coregro.com/
Proseer Website: https://proseer.co/
Book a Consultation: https://proseer.co/contact/
Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/ 


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 Patrick Dichter, founder and owner of AppleTree Consulting, an accounting firm specializing in outsourced accounting and tax services for small to medium-sized businesses. Patrick shares his unique journey from business consultant to accounting firm owner, having grown his company from $1.2 million to $4.5 million in revenue through strategic acquisitions and organic growth. He offers candid insights on the challenges of change management, the reality of scaling a professional services firm, and the difficult decisions that come with rapid growth. From navigating client transitions to building accountability systems and expanding service lines, Patrick pulls back the curtain on what it really takes to build a modern accounting practice. Whether you're considering an acquisition, scaling your firm, or simply trying to build the right team, this episode is packed with real-world lessons from the trenches.


Episode Chapters:


00:00 Introduction: Patrick's Unconventional Path to Accounting


05:00 Change Management: Why Team Transitions Are Harder Than Client Transitions


08:00 Acquisition Lessons: What Worked, What Failed, and Why


11:00 Building Multiple Revenue Streams and Service Lines


14:00 The Reality of Scaling: Growth Sweet Spots and Growing Pains


19:00 Creating a Culture of Accountability with Scorecards and KPIs


22:00 Strategic Planning: Reaching the $5 Million Milestone


26:00 Systems and Technology for Scale: EOS and Practice Management


30:00 Flying Solo: The Pros and Cons of Single Ownership


32:00 Rapid Fire: Books, Metrics, and Essential Business Advice


Episode Resources:


Patrick Dichter on Twitter (X): https://twitter.com/PatrickDichter


Patrick Dichter on LinkedIn: https://linkedin.com/in/patrickdichter


AppleTree Business Website: https://appletreebusiness.com


Book: Unreasonable Hospitality by Will Guidara: https://amazon.com/Unreasonable-Hospitality-Remarkable-Restaurants-Business/dp/0593418573


Book: The E-Myth Revisited by Michael E. Gerber: https://amazon.com/Myth-Revisited-Small-Businesses-About/dp/0887307280


Canopy Practice Management: https://getcanopy.com


Traction (EOS - Entrepreneurial Operating System): https://eosworldwide.com


Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH


Proseer Website: https://proseer.co/


Book a Consultation Contact Us: https://proseer.co/contact/


Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/



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 Kevin Diemar, a powerhouse in private aviation and seasoned angel investor, for his second appearance on the show. Kevin shares his fascinating journey into angel investing, starting with an impromptu investment in a men's yoga shorts company that became his greatest success. He reveals how he sources deals, evaluates opportunities, and builds relationships with founders across various industries—from apparel and mobility scooters to water brands and nutritional supplements. Kevin unpacks the importance of founder authenticity, the power of distribution channels, and why he invests in products he'd personally use. This episode is packed with actionable insights for founders seeking investment and entrepreneurs looking to diversify into angel investing.

Episode Chapters:

00:00 Intro: Kevin Diemar Returns to Discuss Angel Investing01:30 How Kevin Got Started: From Shorts Purchase to Series A Investment07:44 Building Deal Flow and Learning from Winners vs. Losers15:26 The Importance of Communication and Financial Discipline22:17 The Liquid Death Investment: Distribution as a Key Factor29:21 Investment Process: From Product Testing to Founder Due Diligence34:16 Return Expectations and Secondary Market Strategy42:19 Sourcing Deals: Being a Hunter in Angel Investing43:13 Lightning Round: Pitch Deck Essentials, Metrics, and Founder Advice

Episode Resources:
Kevin Diemar on LinkedIn: https://www.linkedin.com/in/kevindiemar
Unity Jets: https://unityjets.com/
Vuori Clothing: https://vuoriclothing.com/
Liquid Death Water: https://liquiddeath.com/
Vuori at REI: https://www.rei.com/b/vuori

Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH

Proseer Website: https://proseer.co/
Book a Consultation Contact Us: https://proseer.co/contact/
Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/ 

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 Jonathan Hayek, a commercial real estate investor and host of "The Source of Commercial Real Estate" podcast. Jonathan shares his remarkable journey from special education teacher to successful industrial real estate investor, offering actionable insights on transitioning careers, building wealth through real estate, and scaling from residential to commercial properties. He discusses overcoming limiting beliefs about income, creative financing strategies for new investors, and why he pivoted from small multifamily properties to net-leased industrial assets for true passive income.


Episode Chapters:


00:00 From Teacher to Real Estate Investor02:05 Why Real Estate?05:08 First Deal Breakdown10:46 Getting Comfortable with Debt16:56 Transitioning to Industrial Properties25:40 Why Syndications Are Struggling29:20 Navigating Market Cycles33:38 Real Estate Tax Benefits36:30 Betting on Yourself38:23 Rapid Fire Questions


Episode Resources:


Jonathan Hayke on LinkedIn: https://www.linkedin.com/in/jonathan-hayek-cre/ Jonathan Hayke Website: jonathanhayek.co What It Takes by Steve Schwarzman (Amazon): https://www.amazon.com/What-Takes-Lessons-Pursuit-Excellence/dp/1501158147 BiggerPockets Real Estate Podcast: https://www.biggerpockets.com/podcasts/real-estate Monday.com Project Management Software: https://monday.com/ 

"The Source of Commercial Real Estate" Podcast - Available on all podcast platforms

Follow Jeff

Jeff Rudner on LinkedIn: https://bit.ly/3DEGINHProseer Website: https://proseer.co/ Book a Consultation Contact Us: https://proseer.co/contact/ Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/ 



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 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