Double Triple Tech Sales Podcast

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 you've been curious about tech sales but weren't sure where to start, start here.

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.

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!

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.

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 he went from 100 cold calls a day in recruitment to leading sales teams, why he treats his career as a series of campaigns instead of jobs, and the decision framework he uses for every big career move.Whether you're trying to break into tech sales or you're already in and thinking about your next move, this is the honest conversation about equity, IPOs and building real wealth in this industry.

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.

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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.

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 he interviews them harder than they interview him, and the hiring philosophy that took a barista with zero tech background to top SDR and a promotion into a closing seat.If you're breaking into tech sales or pushing for your next role, his three career principles at the end are worth the full listen. You're interviewing for your next role from day one. You're promoted by your peers. And your network compounds longer than you think.

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.

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.

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.

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 most recently Grafana as the Regional Sales Director. We get into what separates the top 1% of reps, why qualification is the whole game, how to multi-thread a big four bank properly, and the three personas you have to map in every enterprise deal.If you're an AE weighing up leadership, or a commercial rep who wants to move into enterprise without getting exposed in the room, this one is for you.

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 a strategic deal across the line when you're getting knocked back a hundred times. You also get a behind-the-scenes look at a day in the life with Caelah and Gabe on the way into the city. If you're trying to break into tech sales or level up from commercial to strategic AE, this one's a masterclass.

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% of failed AI pilots fail on transformation, not techWhat AI orchestration really is, and why Mono is not just an LLM wrapperThe Lendi transformation story and why the future CEO is technology-basedHow Mono landed 8 enterprise logos and converted 100% of pilots in one quarterWhy command of the message, MEDDIC and real discovery still win in the AI eraBuilding an agentic Client Intelligence tool to keep pipeline honestHiring for judgment and EQ over raw IQSemantic memory, agent bloat, and the agentic harnessIf you are selling into the enterprise, building in AI, or trying to understand what real AI transformation looks like in 2026, this is the episode.

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.

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."

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.

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 high performer, this episode is for you.

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 of Mindset in Sales11:43 Finding the Right Fit: Maddie's New Role14:57 The Value of Experience and Networking17:44 Embracing Change: The Future of Tech Sales20:44 The Need for Essential Services in Business23:55 Advice for Aspiring Sales Professionals27:04 The Role of Hard Work in Success30:02 Looking Ahead: Maddie's Exciting Future#techsales #B2BSales #SaaSSales

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 has finally become reality.Topics covered:Why Wonderful deploys in-region with forward-deployed engineersThe shift from SaaS to agentic platforms and what it means for enterprise buyersHow Wonderful evaluates founder archetype and risk tolerance when hiringThe real cost-benefit of agentic AI versus traditional headcountWhy human connection matters more, not less, as AI scalesWhat's next for Wonderful and the agentic AI frontierIf you're building, selling into, or considering a move into the agentic AI space, this conversation is a real look at what it takes to build at the frontier.

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 change their lives doing it.Chapters: 00:00 Intro & welcome01:15 Tahlija's origin story: market stalls, retail & studying marketing04:30 Media sales at oOh! Media — burnout, debt & nearly quitting08:00 The friend who handed her a tech role09:30 Marketing vs sales: why listening beats being the loudest in the room12:00 The moment sales clicked as a career14:30 KPIs as a tool, not pressure (& the Deloitte lesson)17:00 Consistency over time — the sports analogy19:00 Landing ServiceNow: the 3-month talent-pipeline interview22:00 Big vendor vs scale-up: where should you start?25:30 What she looks for when hiring (and the AI-polished red flag)29:00 Cold calling, Orum & coaching with data32:00 LinkedIn & personal brand at work34:00 Her leadership style: extreme ownership + radical candor37:00 Managing expectations: BDR to AE & finding your "why"40:00 Motherhood & returning to work in tech43:30 Final advice: there's no one "right" background for tech salesFollow on Instagram @caelahstanleyFollow on LinkedIn @caelahstanleyFollow on Instagram @GabemarzanoFollow on LInkedIn @Gabemarzano#techsales #B2BSales #SaaSSales #technology

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.Chapters00:00 Introduction to Career Pivoting02:51 Navigating the Transition to Tech Sales06:01 The Importance of Positioning and Profiling08:55 Interview Preparation and Presentation Skills12:02 Leveraging AI in the Job Search15:03 Building Relationships with Recruiters and Hiring Managers17:51 The Role of Community Support20:57 Final Thoughts and Advice for Aspiring Tech Sales ProfessionalsFollow me on Instagram @caelahstanley#techsales #B2BSales #SaaSSales #accountexecutive

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 the SDR seat on the right rocket ship beats the AE title on the wrong one, and the exact traits that separate the top 1% from everyone else, relationships and "what's in it for them," a relentless sense of urgency, and professional persistence. We also got real about the numbers: what enterprise AEs actually earn, how OTE, accelerators and stock options stack up, and why he's seen top reps clear over $1.5M in their strongest years.If you want to understand how to evaluate a tech company before you join it, how to break in from outside the industry, and what it really takes to earn like a top 1% rep, this is the episode.Follow on Instagram @caelahstanleyFollow on LinkedIn @caelahstanleyFollow on Instagram @GabemarzanoFollow on LInkedIn @Gabemarzano#techsales #B2BSales #SaaSSales #technology

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 traditional security models. The conversation was fire.We covered how Duncan got into tech sales, how it changed the trajectory of his life, and how it sparked the entrepreneurial drive that led him to build something of his own. If you've ever wondered what the path from rep to founder actually looks like, this is the episode.Follow on Instagram @caelahstanleyFollow on LinkedIn @caelahstanleyFollow on Instagram @GabemarzanoFollow on LInkedIn @Gabemarzano#techsales #B2BSales #SaaSSales #technology

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 grow, and want to build a career that combines people skills, problem-solving, and financial freedom, this one’s for youCheck out all my socials:Instagram: caelahstanley 🔔 Subscribe for more content on tech careers, mindset, and building wealth through high-performance sales.