Wings & Sales

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.

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.

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.

In this raw, unscripted live episode, Vincent and Simba dive into the mental toughness it takes to survive and thrive in tech sales. From cold calling C-suite execs to getting ghosted on LinkedIn, they unpack the wins, the facepalm failures, and the psychology behind rejection.

You’ll learn:

• How to gamify rejection and stay sharp on the phones

• The 3 sales skills every SDR and AE must master (Sales, Product, Business acumen)

• The difference between sales as a means to an end vs a means to a start

• Real tactics for objection handling (NLP, NEPQ, tonality, and mental reframing)

• Reddit’s darkest truths about burnout in sales—and how to protect your mental health

🔥 A must-listen for anyone in B2B sales chasing targets, building mental grit, and staying human in the process.

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.

Another Linkedin Live #2

Shoutout to our 2 viewers!

We reflect on the week thats been in sales, wins, setbacks, and stories.

Key Topics:

- how mindset, routine, and emotional discipline shape sales performance.

- how to master cold call objections

- how to deal with burnout and rejection,

- objection-handling techniques

- why tonality > script

- why your “bad week” doesn’t mean you're bad at sales.

Plus: Reddit stories, sales memes, and why your personal habits could make or break your pipeline.

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.

Linkedin Live #2 — Ep. 16 of Wings & is here!

Vincent and Simba dive into the chaos of sales life, lessons from mock discovery calls.

Why listening beats scripts every time.

Then we took it to Reddit, breaking down a viral post from a burnt-out AE questioning if sales is really worth it

Key Topics:

• the value of being adaptable in Chaos

  Why you need to follow the prospect, not the script

• The emotional rollercoaster of your first discovery call

• Real Reddit rants about burnout, startup, quota

• Why sales is like dating?

• a bit of Jeremy Miner, EQ and the power of listening

  
  

🔥 Real, raw, unscripted, authentic if you’ve ever questioned your career in sales, this episode is for you.

DISCLAIMER: this is for purely entertainment purposes. We are not professionals and this does not represent our companies. These are our own opinions, and for fun. Please consult your manager or a professional.

Linkedin live #1

What does ChatGPT have in common with Sales?

Why is it important to be adaptable in Sales?

This episode delivers raw & authentic insights, and a hilarious breakdown of how to read the room, close deals, and dress like a chameleon.

Key Topics:

1. How AI is changing sales, e-commerce & cybersecurity

This was recorded in Jan 2025.

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.

Why do you need to be curious?

Dive into some philosophical, deep sales chats.

Tune in Fellas.

What's the game of referrals?

How do you work smart not hard?

How did Marc break the sales record at his company?

Find out more in this episode.

We're back and better. It's been 7mths since the last episode.

We haven't stopped recording.

We've been too busy and had no time to edit the podcasts.

We've got at least another 10 episodes coming!!!

Check out the LinkedinLive!

How do you stand out as a salesperson on the phone?

What's the importance of building relationships?

Why does persistence pay off?

Find out more about what strategies Marc implements.