Sales Rewritten – Details, episodes & analysis
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Sales is changing fast.
Sales Rewritten is where the people making it happen share what’s really working.
No scripts. No fluff. Just honest conversations with founders, sales leaders, and reps rewriting the playbook for 2025.
Powered by Surfe - because great sales starts with better data.
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Living the ‘Boujee’ Life - From TV to WeTransfer…The Making of The Follow-Up Queen | Sales Rewritten
Season 1 · Episode 1
lundi 27 octobre 2025 • Duration 52:07
Sales Rewritten (S1E1) - Evelyn Oluwole, The Follow-Up Queen
From selling £20 classified ads to closing six-figure global deals, Evelyn Oluwole has lived every side of sales. In this first episode of Sales Rewritten, a podcast by Surfe, host Alex Wood sits down with WeTransfer’s Global Senior Sales Director to talk about the mindset, mistakes and moments that made her The Follow-Up Queen.
She explains:
◼️ How she started her career in TV
◼️ Why she used to cold call HUNDREDS of businesses selling classified ads
◼️ Built a global sales career and closed a six-figure deal
◼️ Nearly won Spotify as a client
◼️ Uses her “follow-up cheat code”
00:00 Intro
02:23 How to Sell Yourself
03:07 The Negative Stereotypes of Sales
04:51 Starting Out In TV
06:48 Selling Classified Ads
08:25 'One of the Best Roles I Ever Had'
09:37 It's Sink Or Swim
10:36 Why Do You Love Working In Sales?
11:32 The Thrill of the Chase
12:02 Difficult Cold Call Experiences
13:42 'I Never Won a Client on a First Call!'
14:45 The Making of...The Follow-Up Queen
16:32 What Is Follow-Up Strategy?
19:56 How to Follow-Up When You're Busy
20:20 Why You Should Never Use 'Just' In Your Follow-Ups
21:23 AI in Sales
24:04 'People are Thirsty for Human Touch'
24:43 Best Outreach Channels
25:50 Having an Opinion Shows You Care
26:48 Using LinkedIn Like a Pro
29:03 The Pressure of Sales
31:03 Why No Isn't Always Negative
33:16 'I'm Now Giving You Something You Need to Hear'
35:23 Inside WeTransfer
37:33 What's the Biggest Thing That's Changed in Sales?
40:24 Biggest Deal Ever Closed
42:06 Nearly Winning Spotify as a Client
45:05 Email, Call or LinkedIn?
46:20 What's Next for The Follow-Up Queen?
47:34 Do Sales Stereotypes Still Exist Today?
48:42 Going From Rep to AE
49:39 What Does Success in Sales Look Like?
51:09 Outro
If you’ve ever wondered how top performers stay motivated, handle knock-backs and stay sane in sales, this conversation is for you.
The Sales Rewritten podcast is a raw, honest account of sales - for salespeople, by salespeople. Brought to you by Surfe, the high quality data platform that makes prospecting easy.
Follow Evelyn:
LinkedIn - https://www.linkedin.com/in/evelynoluwole/
Instagram - https://www.instagram.com/thefollowupqueen/
Sales Rewritten:
📺 Watch on YouTube: @surfehq
🎙 Listen on Spotify, Apple Music & all major platforms
Sponsored by:
Surfe - https://tinyurl.com/cxexkrjx, start your 14-day free trial today
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