Hunters and Unicorns

• How Dan Fougere Scaled 4 Billion-Dollar IPOs (And What He’d Do Differently)

  In this episode of THE PLAYBOOK UNIVERSE, we sit down with legendary CRO Dan Fougere, a pivotal force behind FOUR $1B IPOs. From engineering roots to building elite go-to-market engines, Dan unpacks the battle-tested frameworks that turned great ideas into generational companies. He shares hard-won lessons from PTC, BladeLogic, Medallia, and Datadog—including how to scale a sales org, recruit world-class talent, and align GTM with visionary founders. Whether you're a startup founder, CRO, or early-stage sales leader, this is a masterclass you don’t want to miss. Dan also reveals the make-or-break mindset shifts that helped him navigate adversity, imposter syndrome, and the constant pressure of building under extreme constraints.   This episode is packed with insights you simply won’t find in any sales playbook. 🙌 Thanks to our Sponsors! PG AI: https://www.getpg.ai Selr: https://selr.ai 🏹 Key Topics Covered 00:00 Intro 02:00 Dan’s 4 IPO Journey 06:45 Why Mentorship Mattered Most 12:00 Building Datadog’s GTM from Scratch 19:30 When Founders Should Hire a CRO 26:00 Go-to-Market Mistakes Startups Keep Making 32:00 The Wrong Way to Hire Sales Leaders 36:30 Datadog’s Hardest Challenges 42:00 Leading Through Pressure & Burnout 48:00 The Power of Having Great Mentors   💥 3 Biggest Lessons 1. Your job as CRO is to make the CEO successful. Leadership alignment and trust are the ultimate foundations for scalable growth. 2. Play the long game—optimize for learning, not short-term comp. Dan’s biggest career leaps came from choosing mentorship over money. 3. Don’t break what’s working—build what doesn’t exist. Great GTM leaders complement product momentum by filling strategic gaps, not overhauling systems. 🙌 Thanks for listening! This episode was hosted by Simon Kouttis and Ollie Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro If you enjoyed this episode, please drop a like/share and subscribe to our channel!   🦄 Connect with Hunters & Unicorns: 🌐 Website: http://huntersandunicorns.com 🐦 Twitter: http://twitter.com/HuntersUn1corns 📸 Instagram: http://instagram.com/huntersandunicorns 📝 Blog: http://huntersandunicorns.com/blog   💬 Borrow These Quotes from Dan! 🗣 “My job as a CRO is to make the CEO successful. Period.” 🗣 “Great sales orgs win even with an average product. That’s the secret.” 🗣 “Don’t try to fix what’s already working—go build what doesn’t exist.” #softwaresales #huntersandunicorns #playbookuniverse

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• Saving a DEAD DEAL Against All Odds, w/Jennifer Ortegón

  In this episode of RAW STORIES LIVE, we sit down with Jennifer Ortegón, Enterprise Account Executive at Harness, to hear how she saved a major account on the verge of churn. With an RFP already in motion and a competitor lined up to replace them, everything was stacked against her. Jennifer had to dig deep, rebuild trust, and take a bold approach. From gathering data to relentless preparation, she and her team refused to back down, showing up day after day until they changed the game. This is a masterclass in resilience, strategic thinking, and leadership in high-stakes sales. 🏹 Key Topics Covered: 00:00 Intro 1:15 A crushing loss 4:16 The account no one wanted 8:03 The turning point 10:52 Winning back trust 12:46 The emotional moment 14:38 Lessons in resilience   💥 3 Biggest Lessons: 🔥 Data is power – Understanding real usage data gave Jennifer the leverage to turn the deal around. 🔥 Trust is earned through action – Showing up consistently and demonstrating commitment made all the difference. 🔥 Own the problem, own the solution – Jennifer refused to let go, took full ownership, and transformed a losing situation into a victory.   🙌 Thanks for listening! This episode was hosted by Simon Koutis and Ollie Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro. If you enjoyed this episode, please drop a like/share and subscribe to our channel! 🔗 Episode’s Links: Jennifer Ortegon on LinkedIn: https://www.linkedin.com/in/jenniferortegon/ Harness Website: https://www.harness.com 🦄 Connect with Hunters & Unicorns: 🌐 Website: http://huntersandunicorns.com 🐦 Twitter: http://twitter.com/HuntersUn1corns 📸 Instagram: http://instagram.com/huntersandunicorns 📝 Blog: http://huntersandunicorns.com/blog   💬 Notable Quotes: "This will be different." – Brian Johnson "We just kept showing up every day until we won the deal." – Jennifer Ortegon #rawstorieslive #softwaresales #huntersandunicorns

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• I Took the BIGGEST Risk of My Life—Here’s What Happened, w/Josh Bey

  In this episode of RAW STORIES LIVE, we sit down with Josh Bey, VP of West & APJ at Obsidian Security, as he shares the gripping story of how he turned a seemingly unwinnable deal into a game-changing success. Facing financial pressure & personal life challenges, Josh breaks down the emotional investment, strategic pivots, and relentless determination that ultimately secured a massive win. This episode dives deep into the importance of resilience, the power of champion-building, and the art of navigating high-stakes negotiations. 🏹 Key Topics Covered: 00:00 - Intro 02:19 - A Scrappy Patch & an Unproven Market 05:11 - The Deal No One Believed In 07:08 - The Pivotal Meeting 08:59 - The Missing ‘Why Now’ 10:32 - Finding the Real Champion 11:38 - Everyone Gave Up, But I Had No Choice 13:29 - The Biggest Lesson in Deal Making   💥 3 Biggest Lessons: 1️⃣ Emotional investment can blind you – A deal isn’t real until you align it with the customer’s true business drivers. Personal stakes don’t equal urgency for the buyer. 2️⃣ The "why now" follows the "why anything" – If your deal lacks a compelling reason for change, there is no urgency. Customers must see value beyond just your product. 3️⃣ The real champion is the one who benefits the most – Look beyond those who like your solution. The real decision-maker is the one who gains money, a promotion, or influence. 🙌 Thanks for listening! This episode was hosted by Simon Kouttis and Ollie Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro If you enjoyed this episode, please drop a like/share and subscribe to our channel! 🔗 Episode's Links: 🔹 Connect with Josh Bey – https://www.linkedin.com/in/joshuabey/ 🔹 Learn more about Obsidian Security – https://www.obsidiansecurity.com/ 🦄 Connect with Hunters & Unicorns: Website: http://huntersandunicorns.com Twitter: http://twitter.com/HuntersUn1corns Instagram: http://instagram.com/huntersandunicorns Blog: http://huntersandunicorns.com/blog   💬 Notable Quotes: 📢 "If you don’t have a strong enough ‘why anything,’ you’ll never get a ‘why now.’” – Josh Bay 📢 "Customers don’t care about your fiscal year or personal stakes. They care about their business needs." 📢 "Find the champion who has something to gain—more money, a promotion, or expanded control." #rawstorieslive #softwaresales #huntersandunicorns

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• How a Simple MISTAKE Led to a 7-Figure Deal, w/John Behm

  In this episode of RAW STORIES LIVE, we sit down with John Behm, VP of Enterprise Sales at Harness, and a seasoned sales leader with a track record of building elite sales teams. John shares his journey from the early days in sales to leading high-performing teams, diving deep into the mindset, strategies, and lessons that drive success. Whether you're a sales professional or a leader looking to elevate your team's performance, this episode is packed with raw insights and practical advice you won’t want to miss. 🏹 Key Topics Covered: 00:00 Intro 02:10 John's First Role in Sales 05:45 Learning from Early Mistakes 09:20 The Key Traits of High-Performing Sales Leaders 12:35 How to Build and Scale an Elite Sales Team 15:50 Takeaways 💥 3 Biggest Lessons: 1️⃣ Success Starts with the Right People – John emphasizes that recruiting and developing the right talent is the foundation of any high-performing sales team. Skills can be taught, but mindset and drive are critical. 2️⃣ Leadership is About Empowerment – Effective sales leaders don’t just manage; they inspire, coach, and create an environment where their teams can thrive. John shares how he fosters a culture of accountability and excellence. 3️⃣ Adaptability is Key to Scaling – As organizations grow, sales strategies must evolve. John discusses how flexibility, data-driven decisions, and continuous learning are essential for long-term success. 🙌 Thanks for listening! This episode was hosted by Simon Kouttis and Ollie Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro. If you enjoyed this episode, please drop a like/share and subscribe to our channel! 🔗 Episode's Links: John Behm on LinkedIn: https://www.linkedin.com/in/john-behm-75935120/ Harness Website: https://www.harness.com 🦄 Connect with Hunters & Unicorns: Website: http://huntersandunicorns.com Twitter: http://twitter.com/HuntersUn1corns Instagram: http://instagram.com/huntersandunicorns Blog: http://huntersandunicorns.com/blog 💬 Notable Quotes: "Great sales teams aren’t built overnight; they’re built with intention, process, and the right people." "The best leaders don’t just push results; they develop people." "Sales success is about consistency—show up, do the work, and keep improving." #rawstorieslive #softwaresales #huntersandunicorns

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• Authenticity and the Human Side of Sales, w/ Hillary Unis

  In this episode of RAW STORIES LIVE, we sit down with Hillary Unis, an account executive at Harness with a wealth of experience navigating high-stakes deals and driving impactful results. Hillary shares her journey through the challenges of enterprise sales, her approach to building trust with clients, and how she stays resilient in the face of adversity. This conversation is packed with actionable insights for sales leaders and anyone looking to elevate their game. Hillary also discusses the importance of aligning personal values with professional goals, strategies for standing out in competitive markets, and how to lead with authenticity. Her passion for empowering others shines through in every story she shares. Whether you’re in sales, management, or simply interested in hearing a candid and inspiring journey, this episode has something for everyone.   🏹 Key Topics Covered 00:00 Intro 02:12 Breaking Barriers and Building Trust 05:30 Handling Setbacks with Resilience 08:40 Strategies for Standing Out in Competitive Markets 11:20 Aligning Values with Professional Goals 15:10 Leadership Lessons and Empowering Teams   💥 3 Biggest Lessons 1. Resilience Leads to Growth: Hillary highlights how setbacks are opportunities to learn and grow, emphasizing the value of persistence in sales. 2. Authenticity Builds Trust: Success comes from being genuine and aligning your values with your professional goals. 3. Leadership Is About Empowerment: Great leaders focus on uplifting their teams and fostering an environment where everyone thrives. 🙌 Thanks for listening! This episode was hosted by Simon Kouttis and Ollie Kuehne, founders of Hunters & Unicorns, and post-produced by the team at videoforce.pro. If you enjoyed this episode, please drop a like/share and subscribe to our channel! 🔗 Episode's Links: Hillary Unis on LinkedIn: https://www.linkedin.com/in/hillary-unis/ Harness Website: https://www.harness.com 🦄 Connect with Hunters & Unicorns: Website: http://huntersandunicorns.com Twitter: http://twitter.com/HuntersUn1corns Instagram: http://instagram.com/huntersandunicorns Blog: http://huntersandunicorns.com/blog   💬 Notable Quotes "Trust is the foundation of every successful deal. Without it, you have nothing." – Hillary Unis "The best leaders empower their teams to achieve greatness together." – Hillary Unis #rawstorieslive #softwaresales #huntersandunicorns

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