Double Triple Tech Sales Podcast

Jessie spent most of her career in the beauty industry, running her own clinic before moving into sales. She never thought tech could be for someone with her background. In this case study, she shares how she made the switch into a fully remote tech sales role in cyber. Caelah sits down with her to break down how she did it. Why beauty was more sales-driven and capped than people realise, which sk...

Chris spent a year in tech five years ago at an early startup, building a sales function from scratch with nobody to tell him if he was doing it right. He left. Then spent years in financial advice looking fro the outside where Tech Sales Reps were making a lot of money. (Apologies there is a few audio issues in this episode). He joined Double Triple, ran five interview processes at once, and came...

Rania is an SDR team leader at Flair (MYOB) and a sales leader of nearly a decade. She'd been searching for over a month, reaching out across LinkedIn, with no luck finding the right SDR, until she turned to Double Triple and had a shortlist of vetted candidates in front of her. In this discussion, Gabe sits down with her to break down the hiring side of the story. Why she now hires for attitu...

In this video I break down Predictable Revenue by Aaron Ross, the book that built Salesforce’s sales machine, and whether it still holds up in 2026.I cover the system behind predictable pipeline, how the SDR, BDR, AE and account management roles fit together, how to build your ICP and outreach sequences, base vs commission-only roles, and how I used all of it across my career at Splunk and Move Wo...

Elizabeth spent seven years in events at Curtin University and hit the ceiling. No room to grow, no path forward, and two young kids at home in Perth. In this episode she walks through exactly how she ran the interview process. The questions she asked peers about real quota attainment. Along with how to choose the best company for you.

Jack spent 12 years in medical device sales, five of them at Stryker, before making the move into tech. In just 5 weeks with Double Triple, he landed an Account Executive role at Salesforce. In this discussion, Gabe sits down with him to break down how he did it. Why he drew a line in the sand and committed fully, how he used a healthcare "wedge" to target roles where his experience was...

In this video I breakdown how to operate like a top 1% SDR, from structuring your day and cold calling to copywriting, multi-threading and getting promoted fast. It’s pulled from 7 years in tech sales, 14 months as an SDR generating over $13M in pipeline, then closing $7M+ in enterprise SaaS deals as an AE.

James spent years in physiotherapy before deciding it was time to go all in on a career change. What started as watching the Double Triple team live a different kind of life on Instagram turned into a full pivot into tech sales, ending with an SDR role at Megaport. In this episode James breaks down how he treated the job search like a sales pipeline (35 opportunities logged), and how his very firs...

Steve wasn't looking to break into tech, he'd been in it for six years. What he wanted was a real sales system. In this case study, he shares how Double Triple's TRIPLE certification and AI training changed the way he sells, and why he rolled it straight into his own company. Gabe sits down with him to unpack how he replaced a loose "dumping ground" of experience with a singl...

Bryce shares his journey from physiotherapy to a career in tech sales, highlighting transferable skills, the role of mentorship, and the impact of strategic action. Discover how Bryce navigated career change, the importance of perseverance, and the support systems that helped him succeed.

In this video Gabe and I run a full mock tech sales interview, breaking down the top 25 most common questions asked in the interview process. These are pulled from real interviews across 80+ clients placed into SDR, BDR, AE and account management roles. Whether you’re breaking into tech sales with no experience or levelling up your current sales career, this is the complete interview prep guide.

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 Jame's land the right role.

Dan spent 16 years as a chef, working up to exec chef running two restaurants, before making the move into tech sales. No tech background, no sales experience. With Double Triple, he landed an SDR role at Kong, matching his six-figure chef salary at entry level, with his first week onboarding in Japan. In this case study, Caelah sits down with him to break down how he did it. Why he wanted out of...

From carpenter tech sales Account Executive in 6 weeks. Jarrod spent 20+ years in Victorian construction qualified carpenter, then rigging and operating mobile cranes on the big build projects. 3:30am starts, rotating night shifts, and a growing sense that there had to be something else. He joined Double Triple, did two weeks of classes, flew to Vietnam with his family, came back, and landed an Ac...

Recorded June 2026, Full podcast originally aired on Tomorrow's Mind with Ben Handler. In this episode, she shares the lessons behind every career pivot, why experience isn’t always the biggest factor in success, and the belief that helped her pursue opportunities others would have talked themselves out of.

A new opportunity is emerging in the world's most innovative industry, but most people are still trying to reach it through a hiring system that is completely broken. After building a cybersecurity business from $4M to $100M with no tech background and no degree, I decided that rather than fix the broken system, we would create a new one. In this video, I break down the eight core beliefs Doub...

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 Katie's first week inside Double Triple looked like.

Recorded October 2026, Full podcast originally aired on Ben Nash on the Mo Money Podcast to share our 5-year journey from having –$50K in cash to building a $4.3 portfolio and 5x-ing our income, all while working full-time in tech sales.

Ornella spent 10 years as an ICU vet nurse across Canada and Australia. She realised about a year in that she'd made the wrong call, but the study, the time and the cost made it feel impossible to walk away. So she pushed through for a decade before finally deciding enough was enough. In this episode she takes us through the full pivot into tech sales, from not even knowing what a BDR was on d...

Recorded October 2025, Full podcast originally aired on the Flamingo Property Investing Podcast with Jack Henderson.

The realistic path to a $300k+ tech sales role and exactly how to get there. In this video I break down where you start, how to climb the career ladder, how equity works and the realistic timeline to achieve this.

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 Alex land the right role.

Recorded May 2026, Full podcast originally aired on Tomorrow's Mind with Ben Handler. In this episode, Caelah breaks down how she got into tech sales, what most people misunderstand about high-income careers, and the shift that took her from being stuck to earning $500k a year.

Between us we've spent 13+ years in the tech sales industry, Caelah went from SDR to strategic AE closing $7M+ in software, and Gabe pivoted from the army into tech, landing an AE role from the start and led sales across the Asia Pacific region for Palo Alto Networks. We go through this video answering a bunch of questions from both sides, the individual contributor and the sales leader. If yo...

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 Leigh land the right role.