The Sign You Are Ready to Lead — Their Win Feels Better Than Yours
How do you know you're actually ready for the next seat and how do you make sure every career move makes you better? In this episode of Hunters and Unicorns, Simon Kouttis and Ollie Kuehne sit down with Matthew Fermino, CRO at Fable Security, to unpack what it really takes to move from top rep to first-line leader, to second-line leader, and all the way to the CRO seat. Matthew explains why he has always optimized his career for development over everything else, why your career should tell a story, and how he knew he was ready to lead: when he took more pride in seeing someone he coached win a deal than in winning one himself. He breaks down the shift from telling to coaching ("people rarely argue with their own conclusions"), how to manage the peers you used to sit next to, and why first-line leaders are the most important role in the entire go-to-market team yet the one companies develop the least. The conversation also covers the jump to second-line leadership, reading the business through data, building leaders who find the answers without you, extreme ownership at every layer, staying close to the field as a CRO, his turning point at Starburst, and why Fable Security is going after the biggest problem in cybersecurity: the human layer. In this episode: • Why you should optimize your career for development, not titles • Why your career should tell a story and the danger of short stints • What real development looks like: tying it to each person's "why" • How to know you're ready for first-line leadership • Why you don't have to promote every great IC • The fundamentals to master before you lead: conviction, forecasting, coachability • Managing the people who were your peers a week ago • Going from telling to coaching • How a brand-new leader recruits A players • Why the best sellers can sell anything • The difference between first-line and second-line leadership • Reading the business through data as you scale • Accountability at every layer of the org • Staying close to the field instead of managing from an ivory tower • His turning point at Starburst, from $1M in revenue and 20 employees to 600 • Building a coaching tree • Fable Security and the human layer of cybersecurity About Matthew Fermino Matthew Fermino is CRO at Fable Security, which is tackling the human layer of cybersecurity the risky behavior behind most breaches. Before Fable, he built his career at PTC, Perfecto and Starburst, where he joined at around $1M in revenue and helped scale the company through rapid growth, including building out Europe and APAC for the first time. About Our Sponsor: Big thanks to Aurasell for sponsoring this episode. Aurasell is an AI-native GTM platform designed to intelligently automate every aspect of the sales cycle from prospecting and deal management to forecasting and coaching. Subscribe to Hunters and Unicorns for more conversations with the leaders building, scaling, and transforming high-growth technology companies. #HuntersAndUnicorns #MatthewFermino #FableSecurity #CRO #SalesLeadership #GTM #RevenueLeadership #SalesManagement #Coaching #Cybersecurity #B2BSales #Leadership Timestamps: 0:00 – Trailer 1:16 – Welcome & Introduction 1:51 – Why You Should Optimize Your Career for Development 2:42 – Short Stints and Why Your Career Should Tell a Story 4:31 – What Development Really Means 5:49 – Learning From Great Leaders at PTC 7:43 – How to Know You're Ready for First-Line Leadership 9:54 – You Don't Have to Promote Every Great IC 11:40 – The Fundamentals to Master Before You Lead 13:11 – Deal Muscle Memory: Seeing Around Corners 15:15 – Managing the Peers You Used to Work Beside 17:44 – Recruiting and Going From Telling to Coaching 20:12 – How a New Leader Recruits A Players 21:49 – Why Leaders Need to Sell the Vision to Candidates 23:25 – Why the Best Sellers Can Sell Anything 25:22 – Learning From Different Leaders and Playbooks 29:09 – First-Line vs. Second-Line Leadership 31:36 – Matthew's Mistakes as a New Second-Line Leader 34:39 – Reading the Business Through Data 37:09 – Developing Leaders Who Find Answers Without You 40:42 – Accountability at Every Layer 42:02 – When Are You Ready for Second-Line Leadership? 44:16 – Breaking Through to Executive Leadership 46:15 – Staying Close to the Field as a CRO 49:36 – Working Cross-Functionally as One Team 51:03 – The Turning Point: Scaling Starburst 55:24 – Building a Coaching Tree 56:53 – Fable Security and the Human Layer 1:00:25 – What's Next for Fable 1:00:59 – Closing







