Double Triple Tech Sales Podcast – Details, episodes & analysis

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Double Triple Tech Sales Podcast

Caelah Stanley and Gabe Marzano

Business

Frequency: 1 episode/4d. Total Eps: 17

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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🇬🇧 Great Britain - careers
18/07/2026
#95

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https://www.youtube.com/hashtag/b2bsales
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https://www.youtube.com/hashtag/techsales
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https://www.youtube.com/hashtag/saassales
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Score global : 21%

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How to Sell Like the Top 1%: 8x President’s Club Veteran Chris McPherson Breaks Down His Playbook

Episode 17

Thursday, July 30, 2026 • Duration 49:28

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.

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How to Close $1M+ Deals in Tech Sales with Ben Lanciano (Part 2)

Episode 16

Sunday, July 26, 2026 • Duration 12:27

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.

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From $15k in Debt to Tech Sales Leader | Tahlija Macdonald

Episode 7

Thursday, June 25, 2026 • Duration 43:57

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 quitting

08:00 The friend who handed her a tech role

09:30 Marketing vs sales: why listening beats being the loudest in the room

12:00 The moment sales clicked as a career

14:30 KPIs as a tool, not pressure (& the Deloitte lesson)

17:00 Consistency over time — the sports analogy

19:00 Landing ServiceNow: the 3-month talent-pipeline interview

22:00 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 data

32:00 LinkedIn & personal brand at work

34:00 Her leadership style: extreme ownership + radical candor

37:00 Managing expectations: BDR to AE & finding your "why"

40:00 Motherhood & returning to work in tech

43:30 Final advice: there's no one "right" background for tech sales

Follow on Instagram @caelahstanley

Follow on LinkedIn @caelahstanley

Medical Sales to Tech Sales ($300k+ OTE)

Episode 6

Sunday, June 21, 2026 • Duration 35:56

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 Tech Sales Professionals

Follow me on Instagram @caelahstanley

#techsales #B2BSales #SaaSSales #accountexecutive

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5x President's Club: The Elite Mindset of the Top 1% from SDR to Strategic AE with Ben Lanciano

Episode 5

Thursday, June 18, 2026 • Duration 46:05

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

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Real Estate to Tech Sales BDR $170K Package In 4 weeks

Episode 4

Sunday, June 14, 2026 • Duration 47:43

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

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From $16M Tech Sales AE to Cyber Founder: Duncan Simpsons path to building CyberAi

Episode 3

Thursday, June 11, 2026 • Duration 01:11:33

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 @caelahstanley

Follow on LinkedIn @caelahstanley

Follow on Instagram @Gabemarzano

Follow on LInkedIn @Gabemarzano

#techsales #B2BSales #SaaSSales #technology

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How Mike Doubled His Income and Landed a Tier 1 AE Role

Episode 2

Monday, June 1, 2026 • Duration 26:49

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

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How Tech Sales Changed Our Lives

Episode 1

Monday, May 25, 2026 • Duration 27:51

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.

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Why 95% of Enterprise AI Pilots Fail | Brad Perriott monō ai

Episode 15

Thursday, July 23, 2026 • Duration 34:32

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.

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Double Triple Tech Sales Podcast – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

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Double Triple Tech Sales Podcast – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

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RSS feed quality and score

Publication history

Latest published episodes

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