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Sales Rewritten

Author: Sales Rewritten

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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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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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