Double Triple Tech Sales Podcast

Adam McCaughey went from $67K in debt and living in his car, to becoming one of the most respected sales operators in the online education space. In this episode of the Double Triple Podcast, Adam goes deep on the mindset that actually separates the people who make it from the people who stay stuck, the "right person, wrong seat" trap, why pain drives more action than pleasure, and how t...

In this episode, Matty shares his inspiring journey from scientist and solo entrepreneur to a successful tech sales professional. Discover how leveraging existing skills, strategic coaching, and community support can accelerate career pivots into high-growth industries like cybersecurity. Connect with us: 📲Caelah Instagram: https://www.instagram.com/caelahstanley/ 📲Caelah LinkedIn: https://www.l...

Dalibor Siroky, GM ANZ at Wonderful, joins Gabe Marzano to unpack how an 18-month-old agentic AI company is scaling to a billion-dollar enterprise business, 30 markets, and a 1,000-person team, all while moving at 10x to 100x the speed of traditional SaaS.In this episode, Dalibor shares his journey from military officer to founder to building Wonderful's agent-first platform for ASX200 enterprises...

Thinking about getting into tech sales, but not sure where to start, or if it’s even worth it anymore? Listen to this episode to hear how we helped Saxon land the right role. Follow me on Instagram @caelahstanley ⁠#techsales⁠ ⁠#B2BSales⁠ ⁠#SaaSSales

Tahlija Macdonald is Head of Sales Development at HiBob, where she's spent ~4 years building and leading the ANZ BDR/SDR team. After starting out in media sales, a world that nearly pushed her out of the industry for good, she made the jump to tech at ServiceNow and never looked back. Tahlija is passionate about one thing above all: helping people from any background break into tech sales and chan...

In this episode, Lee shares his transformative journey from healthcare sales to tech SaaS, highlighting the strategic approach, leveraging AI tools, and the importance of positioning and community support in career pivoting. Chapters 00:00 Introduction to Career Pivoting 02:51 Navigating the Transition to Tech Sales 06:01 The Importance of Positioning and Profiling 08:55 Interview Preparation and...

Ben Lanciano has quietly built one of the most impressive enterprise tech sales careers in the APJ region. Over 10–15 years he's gone from door-knocking the toughest parts of Australia for Fuji Xerox, to taking a pay cut to join Okta as an enterprise SDR, to becoming a top 1% Account Executive selling into some of the largest organisations in the world. He's now at Chainguard, a ~$4B cybersecurity...

Thinking about getting into tech sales, but not sure where to start, or if it’s even worth it anymore? Listen to this episode to hear how we helped Blake land the right role. Follow on Instagram @caelahstanleyFollow on LinkedIn @caelahstanleyFollow on Instagram @GabemarzanoFollow on LInkedIn @Gabemarzano#techsales #B2BSales #SaaSSales

Duncan Simpsons had one of the most impressive tech sales careers I've come across. Closing $16M deals. At the top of the game. Then he did what only a small percentage of top reps ever do, he left to build his own company. He's now co-founder of CyberAI, a cybersecurity and AI partner helping organisations reduce risk, simplify complexity, and move faster, without the cost and drag of tra...

Thinking about getting into tech sales, but not sure where to start, or if it’s even worth it anymore? Listen to this episode to hear how we helped Mike land the right role. Follow me on Instagram @caelahstanley #techsales #B2BSales #SaaSSales

Thinking about getting into tech sales but not sure where to start? In this video, we discuss: 1. The full career path, from SDR to Enterprise AE to leadership, and the realistic earning potential at each stage.2. How we are helping others do the same in tech sales3. Our personal stories breaking into tech sales, the challenges we faced, and what we’d do differently. If you’re ambitious, hungry to...