Scaling companies is hard. Exiting them successfully is even harder. Doing it repeatedly takes a different mindset.

In this episode of Sales Lead Dog, host Chris sits down with Jeff Fleischer, a senior operating executive, capital advisor, and entrepreneur with more than 25 years of experience scaling technology and cybersecurity companies through hypergrowth, acquisitions, and strategic exits.

Jeff has held CRO, SVP, and CEO roles across public and private markets, helping build and sell multiple businesses to acquirers, including McAfee, JPMorgan Chase, Raytheon, BlackRock/Pamplona, and Audax. Today, he is the Founder of ProScale Partners and is launching Grainview Capital, advising founders, private equity firms, family offices, and strategic investors during critical inflection points.

This conversation dives deep into growth strategy, leadership alignment, go-to-market execution, capital formation, and what truly breaks companies during scale. Jeff shares real-world lessons from operating inside fast-moving environments where clarity, speed, and execution matter most.

Whether you’re a founder, operator, executive, or investor navigating growth or preparing for an exit, this episode delivers practical insight from someone who has done it repeatedly.

🔍 What You’ll Learn in This Episode:

- How operators scale companies through hypergrowth - Why leadership alignment is critical to execution - What founders misunderstand about scaling and exits - The role of capital strategy in growth and M&A - Lessons from cybersecurity, AI, and infrastructure platforms

🎧 About Sales Lead Dog

Sales Lead Dog is a podcast for founders, executives, and revenue leaders focused on leadership, growth, culture, and modern go-to-market strategy.

🔗 Connect & Learn More

Guest Links 🔹 Jeff Fleischer on LinkedIn: https://www.linkedin.com/in/jeffreylfleischer/ 🔹 ProScale Partners: https://proscale.ai/

Sales Lead Dog & Resources 🔗 Sales Lead Dog & Resources 🎙️ All Sales Lead Dog Episodes: https://empellorcrm.com/salesleaddog/ CRM Shouldn’t Suck: https://www.crmshouldntsuck.com Empellor CRM: https://www.Empellorcrm.com

👍 Like the video if you found value 📩 Subscribe for weekly founder & operator conversations 💬 Comment below: What stage of growth are you navigating right now?

What starts as a dream of becoming a jazz musician turns into an unexpected journey of building a healthcare technology company impacting millions of lives.

In this episode of Sales Lead Dog, host Chris sits down with Gerry Miller, Founder & CEO of Cloudticity, to explore a career shaped by passion, courage, and the ability to say yes to unexpected opportunities.

Gerry shares how early curiosity for technology, combined with tenacity and bold decision-making, led him from music to cloud computing, healthcare innovation, and AI-driven transformation. The conversation dives deep into leadership, entrepreneurship, culture-building, and how technology is reshaping the future of healthcare.

This episode isn’t just about business it’s about mindset, resilience, mentorship, and creating meaningful impact while building something that lasts.

In this episode, you’ll learn:

- How unexpected career pivots can lead to long-term success - What it really takes to build and scale a healthcare tech company - Why passion and courage matter more than fearlessness - How AI and cloud technology are transforming healthcare - The importance of culture, enablement, and work-life integration

Whether you’re a founder, executive, entrepreneur, or someone navigating change, this conversation offers practical insights and real-world leadership lessons.

🎧 About Sales Lead Dog

Sales Lead Dog is a podcast for founders, executives, and revenue leaders focused on leadership, growth, culture, and modern business strategy. Each episode features real conversations with experienced operators who’ve built and scaled successful companies.

🔗 Connect with Our Guest Gerry Miller on LinkedIn: https://www.linkedin.com/in/gerrymiller Cloudticity: https://www.cloudticity.com

🔗 Sales Lead Dog & Resources 🎙️ All Sales Lead Dog Episodes: https://empellorcrm.com/salesleaddog/ CRM Shouldn’t Suck: https://www.crmshouldntsuck.com Empellor CRM: https://www.empellorcrm.com

👍 Like this video to support the show 📩 Subscribe for weekly founder & leadership conversations 💬 Comment below: What part of Gerry’s journey stood out to you?

Sarah Rahall-Lunsford, the visionary behind Centered Strategies Consulting, joins us to share her unexpected leap from marketing to sales and business development. Her journey began with a simple piece of advice that transformed her approach, leading her to success in helping companies translate their expertise into effective sales strategies, particularly in professional services. Sarah's insights into understanding client needs and matching them with the right solutions frame sales as a service, emphasizing continuous improvement and the power of clear communication to truly stand out.

Our conversation with Sarah explores the fundamentals of effective marketing strategies that enable businesses to differentiate themselves in a saturated market. By honing in on what clients truly want and employing storytelling to highlight the unique benefits of their offerings, businesses can create a memorable impression. We focus on the vital role of data analysis for businesses navigating growth, as understanding trends and improving hit rates can significantly enhance competitiveness and better manage constraints.

Lastly, we dive into optimizing CRM systems and the transformative role of AI. Sarah articulates the challenges businesses face with data management and CRM implementation, advocating for streamlined processes that make data actionable. We discuss the integration of AI tools like Google Gemini and Copilot for Sales, which act as virtual assistants to improve productivity and engagement. Sarah shares her experiences using AI for efficient note-taking and data analysis, offering valuable insights for those looking to leverage AI in their business strategies.

Sarah Rahall-Lunsford brings over 20 years of experience driving business growth through pragmatic, consensus-driven strategies in business development and marketing. She has held senior leadership roles, including Director of Sales and Marketing for an international home furnishings brand and SVP of Business Development for a $450M ENR Top 15 transportation firm.

Sarah has led successful capture planning programs with win rates over 50%, generating $1.5B in contracts over the past decade. She managed a 20-person BD coordinator team, developed training programs, and helped build a national M&A strategy—from research and reporting to strategic intent presentations.

She holds a master’s degree in organizational communication from Pepperdine University, where she led the Speech Laboratory, and a bachelor’s in communication with a journalism minor from Butler University, where she also directed the Speaker’s Lab.

Quotes:

On the Role of Marketing: "In a saturated market, standing out means truly connecting with decision-makers and focusing on what clients want to buy, not just what we want to sell."

On Data Management: "Companies often get trapped in a cycle of maintaining the status quo with CRM systems. It's essential to streamline processes and focus on making data actionable."

Integrating AI Tools: "AI tools like Google Gemini and Copilot for Sales are transforming CRM by acting as virtual assistants, improving productivity and engagement."

Navigating Growth Constraints: "Understanding trends and improving hit rates can significantly enhance competitiveness, helping businesses manage growth constraints more effectively."

On CRM Systems: "A CRM should work for the user, not against them. It's about stripping systems down to essential functions to avoid overwhelming users."

Links:

Sarah’s LinkedIn - https://www.linkedin.com/in/sarah-rahall-lunsford-25883216/

Centered Strategies Consulting - https://www.centeredstrategiesconsulting.com Find this episode and all other

Sales Lead Dog episodes at https://empellorcrm.com/salesleaddog/

Get your free copy of CRM Shouldn’t Suck at https://crmshouldntsuck.com