#21 - S2 From School Teacher to AE — What Teaching Taught Me About Sales | ft. Dillon Reyes
Dillon Reyes spent years as a high school teacher in the UK and Sydney before making a full career pivot into tech sales. Today he's a Senior Account Executive and Team Lead at Huntress — a cybersecurity company where he was hire number two and watched the APAC team grow from 2 to 40 people.
In this episode, we unpack the real journey from SDR to Senior AE, and what it actually takes to build a long-term career in sales.
In this episode you'll learn:
Why the skills that make a great teacher also make a great salesperson — and how to apply them on every discovery call
The mindset shift that separates SDRs who progress from those who plateau — resilience, discipline, and what "you create your own luck" really means in practice
What authentic selling actually looks like?
What makes a great sales leader?
The mental health reality of working in sales
Who this episode is for:SDRs looking to level up, AEs wanting to sharpen their craft, and anyone curious about what a long-term, sustainable sales career actually looks like.
3 Sept 2025
#20 - Season 2: Cold Calling Roulette: Sales Roleplays & Real Lessons
Vincent and Simba are back with an unscripted session of W & Sales Live.
In this episode, we reflect on real cold call lessons from the week—funny responses, permission-based openers, and why in-person meetings still win in 2025.
Then we did a "sales roleplay roulette" wheel—pitching fake products like “Jargon Buster AI” and “CoffeeSync Pro” live on the spot in 2-minute sales calls.
Expect laughs, awkward moments, and surprising takeaways that every SDR and AE will relate to.
Whether you're grinding in tech sales or just want to improve your pitch game, this episode’s packed with insights and raw banter.
Simba’s Cold Call Experiments: Using cheeky permission-based openers like “give me 30 seconds or tell me to go away.”
Top 3 Real Responses: From laughter to polite rejection—how tone and script framing matter.
Vincent’s Lessons:
Going in-person beats digital outreach.
One call can turn into two meetings (even when someone leaves the company).
Always follow up via email—even after rejection.
Live Roleplays:
DISCLAIMER: All advice is general in nature. Please speak to your manager before implementing the tips. We are not professionals, and this is purely for entertainment purposes only.
20 Aug 2025
#19: Season 2 - Will AI replace Sales & The 5AM Club: Mastering Mindset & Momentum
In this unscripted Friday-night special, Vincent & Simba return for a raw, high-energy live episode where they explore how to stay sharp in a sales role—especially when your week gets wrecked by public holidays, rejection, or burnout. From sales books to the rise of AI voice agents, it’s a jam-packed masterclass in adapting, evolving, and staying mentally strong in the SDR/AE game.
🔥 Highlights:
How to regain momentum after a slow sales week
Why Think Like a Monk, The Go-Giver & The 5AM Club make you a better rep
Real talk about AI sales agents (and whether SDRs will be replaced)
How to use Clay for lead enrichment and automating prospecting
Mindset tips: from rejection tallies to learning like it’s 2035
Whether you're day-one in sales or 10 years deep, this episode is your mental edge to win the week ahead.
DISCLAIMER: All advice is general in nature. Please speak to your manager before implementing the tips. We are not professionals, and this is purely for entertainment purposes only.
Podcast Authority Score: 16 / 100
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