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