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:

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