Double Triple Tech Sales Podcast
Double Triple is the #1 tech sales advisory firm in the world. Each week, Caelah and Gabe sit down with guests from across the tech sales industry to talk sales, go-to-market, and the frontier tech companies shaping what's next. They also bring on clients to share their real journeys breaking into and leveling up in tech sales.
Wine Industry to Tech Sales (Account Executive - 10 day interview process)
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.
16 Years A Chef To A Tech Sales Role, Here's How Dan Did It
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 a capped career despite loving the work, how he weighed multiple offers with a simple pros-and-cons approach and his wife, and what actually got...
From Carpenter to Tech Sales Account Executive in 6 weeks
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 Account Executive role. No SDR stepping stone. He interviewed so well in the first round they skipped a stage and sent him straight to offer.In this episode Gabe and Jarrod unpack the whole thing: why...
From Army Diver to Cyber Sales: How Gabe Marzano Built a $100M Business
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.
8 Steps That Take People From 120K To 420K In Tech Sales
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 Double Triple was built on, the same one that has helped hundreds of people increase their income and find more meaningful work.
The people who...
Breaking Into Tech Sales: What Katie's First Week Looked Like Inside Double Triple
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.
How We Built a $4.3M Portfolio & 5x’d Our Income in 5 Years (From -$50K to 3 Properties)
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.
ICU Vet Nurse into 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 day one to landing a role at HubSpot, her number one company.We get into the mistakes she made early (the "one and...
How We Built a $3.5M+ Property Portfolio by 30
Recorded October 2025, Full podcast originally aired on the Flamingo Property Investing Podcast with Jack Henderson.
The Path to a $300k+ Tech Sales Role
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.
From Zero Sales Experience to 6 Figure Tech Sales Role in 2 weeks
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.
The Career Pivot That Took Caelah Stanley from $55k to $500k a Year
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.
Unfiltered Q&A: "Will AI Kill Tech Sales Before I Even Get In?"
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 you've been curious about tech sales but weren't sure where to start, start here.
Break Into Tech Sales From High Ticket Sales (The Exact 10-Day Interview Process)
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.
The Complete Guide to Tech Sales in 2027
We ran a live session to hear how our clients broke into six-figure tech sales careers with no experience!Here's the recording 👇https://webinar.doubletriple.ai/watch-the-replay We got through 30 to 40 questions about breaking in, the day to day, the money, remote work, and everything in between.I was still buzzing from it, so I pulled together all the biggest questions and answered them for you right here!
From Army to Fully Remote $170K Tech Sales Career
Mun-Nee shares his inspiring journey from military service to a successful career in tech sales, highlighting the importance of community, strategic patience, and passion for cybersecurity. Discover how he leveraged the Double Triple program to land a remote role at Huntress and the key lessons learned along the way.
The Truth About Equity and Building Wealth in Tech Sales | Javier Alonso
Everyone talks about the base salary and the commission in tech sales. Almost nobody talks honestly about the piece that actually builds wealth, equity. In this episode of the Double Triple Podcast, I sit down with Javier Alonso, VP of Sales at ACPL, who spent years at some of the biggest names in enterprise software, Gartner, Okta and Netskope, plus rode a startup all the way to IPO.Javier gets real about the equity conversation nobody has with you before you sign and why the "IPO in two years" he was promised took seven. He also breaks down how...
From Niche tech company to $200K+ AE Tech Sales Career
Ash shares his journey through the Double Triple program, highlighting the importance of strategic storytelling, interview preparation, and community support in landing a top tech sales role at Gorgeous. Discover practical insights on role positioning, AI use, and navigating remote work.
From Degenerate to Building a Fitness Empire | Max Hoonhout
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Personal Trainer to a $120k+ Tech Sales Role
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 Daniel land the right role.
What It Takes to Build a Tech Giant in Asia Pacific (4 Times Over) | Matt Loop, Rippling
Matt Loop has spent 20 years building tech companies in Asia Pacific. Joined Salesforce at 250 people. LinkedIn before it hit a million users. Slack through the Salesforce acquisition. Now Head of Asia at Rippling, where he's grown the region from a team of one to 150 plus in three years.In this episode, Matt breaks down what he learned working under Aaron Ross as the Predictable Revenue playbook was being written, why the Microsoft acquisition of LinkedIn produced the best two years of his career, and what Salesforce did differently with Slack.We also get into how he picks companies, how...
Tradie to 6 Figure Tech Sales Role in 2 weeks
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 Cam land the right role.
Why Your "Non-Tech" Background Belongs in Tech Sales | Stephanie Zuniga-Maher
Stephanie Zuniga-Maher spent 20+ years in tech recruitment and talent, and she's actually the person who hired Caelah at Splunk, so having her join us as a coach at Double Triple is a real full-circle moment for me. In this episode we talk about why your "non-tech" background isn't a limitation but an advantage, why the tech industry needs people from every kind of lived experience, and the mindset shifts I see get people hired.
No Tech Experience to 6 Figure Tech Sales Role ($40k to 6 figures a year)
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 Ebony land the right role.
How to Sell Like the Top 1%: 8x President’s Club Veteran Chris McPherson Breaks Down His Playbook
Chris McPherson has made President's Club 8 times across some of the best tech companies in the market. Chris is in the top 1% of great enterprise sales reps. He started as a BDR, stepped into leadership, then handed the role back two years later to go be an individual contributor again. He stayed at the top of the game the whole way through, and he's back leading now. There's nothing like a leader who can lead by example.This conversation covers what happened in between. Starting as a Business Development Representative at 21, working at companies like New Relic, DataBricks and...
How to Close $1M+ Deals in Tech Sales with Ben Lanciano (Part 2)
Ben Lanciano is a Principal Account Executive at Chainguard and a 5x President's Club winner who's built a $1.5M+ career in tech sales. In this bonus part 2, back by popular demand, Ben breaks down the real difference between closing $50K commercial deals and $500K+ strategic enterprise deals: deal velocity, using the channel as a force multiplier, and the "it's not I, it's we" team-selling mindset that separates the top 1%. He walks through the $100K non-profit deal he fought internally to close, the ~$3M team deal that nearly hit his entire annual quota, and the resilience it takes to push...
Why 95% of Enterprise AI Pilots Fail | Brad Perriott monō ai
Brad Perriott has spent more than 20 years selling through every major tech wave: infrastructure, cloud, cyber, and now AI. Today he leads GTM at monō ai, one of the hottest AI startups in Australia, founded by former Lendi CEO David Hyman.In their first quarter, Mono signed eight enterprise customers and converted 100% of pilots to contracts, in a market where 95% of enterprise AI pilots show no measurable return. In this episode, Brad breaks down what actually separates the AI projects that work from the ones that stall, and why the problem is almost never the technology.Topics covered:Why 77% o...
From $60K High Ticket Closer to $180k Tech Sales Rep
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.
What a Tech Sales Director Actually Looks for When Hiring | Luke Napoli
Luke Napoli on the non-traditional path to Tech Sales Leadership and what the journey entails. Caelah and Luke discuss why "go slow to go fast" is important in enterprise tech sales, why he hires for traits over credentials every time, what MEDDPICC is actually for, why your team is your ceiling, and the phrase his first VP used to break him out of being the "super rep."
How Loom Videos Helped Charlie Land a Tier 1 Tech Sales Role
Charlie shares his journey from physio to tech sales, detailing his strategic approach to job hunting, interview prep, and leveraging community resources to land a Tier 1 role. Discover how he used innovative tools like Loom videos and a sales cycle mindset to stand out in competitive tech sales interviews.
From Living in His Car to Forbes: The Sales Mindset Nobody Teaches | Adam McCaughey
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 to make the decision most people talk themselves out of. Whether you're trying to break into tech sales, level up as a rep, or just build the mindset of a...
From Health Coach to Tech Sales AE in 4 Weeks
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.linkedin.com/in/caelah-stanley/📲Gabe Instagram: https://www.instagram.com/gabemarzano/📲Gabe Linkedin: https://www.linkedin.com/in/gabemarzano/📲 Website: https://www.doubletriple.ai/Chapters00:00 Maddie's Journey: From Scientist to Entrepreneur02:44 Navigating Career Transitions: Lessons Learned06:05 The Power of Community and Coaching08:57 The Importance...
Wonderful's Agentic AI Playbook: the $2B+ Enterprise AI Company at 100x Speed with Dalibor Siroky
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. He breaks down what enterprise AI adoption actually looks like in 2026, why security and governance now matter more than the agents themselves, what it takes to hire for high agency and founder DNA, and why the agentic promise...
Professional Footballer & High Ticket Closer into Tech Sales in 3 weeks
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
From $15k in Debt to Tech Sales Leader | Tahlija Macdonald
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 change their lives doing it.
Chapters: 00:00 Intro & welcome
01:15 Tahlija's origin story: market stalls, retail & studying marketing
04:30 Media sales at oOh! Media — burnout, debt & nearly qu...
Medical Sales to Tech Sales ($300k+ OTE)
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 Presentation Skills
12:02 Leveraging AI in the Job Search
15:03 Building Relationships with Recruiters and Hiring Managers
17:51 The Role of Community Support
20:57 Final Thoughts and Advice for Aspiring...
5x President's Club: The Elite Mindset of the Top 1% from SDR to Strategic AE with Ben Lanciano
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 company in the software supply chain security space, and as he puts it, scaling a rocket ship.This conversation was packed. We covered Ben's rogue path into tech sales, why he believes th...
Real Estate to Tech Sales BDR $170K Package In 4 weeks
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
From $16M Tech Sales AE to Cyber Founder: Duncan Simpsons path to building CyberAi
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 traditional security models.
The conversation was fire.
We covered how Duncan got into tech sales, how it changed the trajectory of his life...
How Mike Doubled His Income and Landed a Tier 1 AE Role
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
