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Published by Caelah Stanley and Gabe Marzano
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.
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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.
Ranking source
Apple Podcasts rankings via the Mato Topic Intelligence Platform.
Observed September 19, 2026. Cached outside the daily freshness window; the positions keep the date they were taken on.
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