Double Triple Tech Sales Podcast

Caelah Stanley and Gabe Marzano
  • 0.0 (0)
  • Careers
  • Updated Fortnightly

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.

  1. 1 day ago

    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."

  2. 4 days ago

    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.

  3. 9 July

    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 high performer, this episode is for you.

  4. 5 July

    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 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

  5. 2 July

    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 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.

  6. 28 June

    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

  7. 25 June

    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 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 Follow on Instagram @Gabemarzano Follow on LInkedIn @Gabemarzano #techsales #B2BSales #SaaSSales #technology

  8. 21 June

    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 Tech Sales Professionals Follow me on Instagram @caelahstanley #techsales #B2BSales #SaaSSales #accountexecutive

See All (13)

About

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.

Information

  • Creator
    Caelah Stanley and Gabe Marzano
  • Years Active
    2026
  • Episodes
    13
  • Rating
    Explicit
  • Copyright
    © Caelah Stanley and Gabe Marzano
  • Show Website
    Double Triple Tech Sales Podcast

You Might Also Like