From selling £20 classified ads to closing six-figure deals, Evelyn Oluwole has lived every side of sales. On the first episode of Sales Rewritten, WeTransfer's Global Senior Sales Director explains why the deal is rarely won on the first call.
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Most people picture a pushy seller at their door when they hear the word ‘sales’. Evelyn Oluwole wants to change that. For her, sales is about building relationships, understanding what people need and solving their problems.
That way of thinking has taken her from a runner's job at ITV Studios to a global role at WeTransfer. In episode one of Surfe’s Sales Rewritten podcast, she tells host Alex Wood what she has learned along the way.
Evelyn started out selling £20 classified ads to pattern cutters, by phone, with leads from the Yellow Pages. It was tough, and she still calls it one of the best roles she ever had.
"I never won a business on a first call. It was after the fourth or the fifth call because by then I'd pretty much known everything about them including the name of their cat. Because I had to."
To a micro business, £20 was a real commitment. Before they parted with it, they needed to build trust.
Most follow-ups fail because there is no strategy behind them. Evelyn's approach is to think about why they haven't replied, then come back with something new and useful - not a reminder.
"If you can master follow up, it is the cheat code to success. And when I speak to mentees, the thing I tell them is, okay, what's your follow up strategy? Like, how are you gonna get from A to B?"
In the episode, she breaks down her timing, why the word "just" undermines your message, and why she works 20 to 30 accounts at a time.
A follow-up lands better when it's tied to a reason to reach out. Our guide to B2B buying signals shows what to look for.
Evelyn regularly uses AI in her work, especially for prospect research. But she is clear on its limits.
"AI does not have soul. And when I say AI does not have soul, what I'm referring to is that AI cannot read the room. Like you and I are having a conversation now. And if it's getting a little bit awkward, there's just something, we'll just know."
AI lacks context, and buyers still want real conversation. Her advice is to be active on Business Social, comment with an opinion, and share who you are beyond your job title.
If you want AI and automation to take on more of the research, start with our pick of the best B2B lead generation tools in 2026.
Evelyn also discusses dealing with rejection, the six-figure Clarins deal she won while selling for Yahoo and her advice for reps stepping up to AE.
"It's not about closing, it's about connecting... Sometimes you don't close the deal because it's not right. It's not right for you, it's not right for them."
Knowing when a deal isn't right starts long before the close. Here's why qualifying leads matters as much as closing them.
There is plenty more in the episode, including how Evelyn nearly won Spotify as a client, what selling advertising at WeTransfer involves and what sales stereotypes still exist today.
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Alex Wood tells Surfe's story across every part of the business, from product news to onboarding new users and everything in between. He oversees all aspects of Surfe's video content production, communicating new features and connecting with audiences. Born in the UK. Based in Bristol. Can quote every line of Jurassic Park 🦖
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