Jamie Scarborough


My first job was selling carpet and rugs on my uncle’s market stall in East London (England). I was 14 and it was always cold and wet out. I loved it.

From there, 6 years passed with me selling everything from steak-knives in London pubs (bad idea – don’t try it!) to beer and wine in bars all over the world (great idea – try it often!).

I found myself in Canada at 20 looking to make my fortune. The plan: start my own company; be rich by 22; retire to Barbados at 25. Instead, I got a job with a recruitment advertising agency as a Copywriter (selling companies as a place to work) and by 25 was a rising star Creative Director for the agency (great title, terrible wage).

Something had to change. It did.

My boss – the VP of Creative at the time – became the VP of Sales. She asked me if I wanted to join her on the sales team. I jumped at the chance to make commissions. I spent the next 2 years selling into the Vancouver market. I was friendly, fast-talking and had a big personality (everything I thought you needed to be great at sales). I had some big successes, and some miserable failures, but was well thought of by the company (I was Sales Person of the Year). But I was so frustrated! Why – when I used the same sales approach every time – did I win some deals and lose others? I knew there was a lot more I needed to learn, and I needed to learn it quick. So I packed up my life and joined a sister-company (Monster) in Toronto.

For the first time I was mixing with other sales people and leaders: seasoned vets from all over North America who were hungry and being well-fed. The next 5 years were a Doctorate in Sales (but with them paying me!). I learnt about cold-calling and presenting and negotiations. I learnt about process and discovery and consultation. I learnt why sales is more about empathy than about fast-talking (although fast-talking certainly helps sometimes). I was Sales Person of the Year – twice! More than that, I became a professional sales person.

By the time my 5 years with Monster were up, I was managing the entire Canadian field sales team. People 10-20 years older (with experience to match) came to me for sales advice. My team had grown its revenues by 400% in my tenure (highest growth in Monster globally!) and had emerged as the Canadian market leader. I had done everything I could do and was being fast tracked for senior management. But I felt I had learnt everything I could there and wanted to make a change.

I was recruited back to Vancouver as the VP of Sales for Hcareers.com – a global hospitality job board. Great company, great opportunity, GREAT location (big Vancouver fan!). They let me completely overhaul their sales operations and – 1 year in – I was ready for my next challenge.

Today I am one of the owners of Sales Talent Agency. A Canadian company that finds quality sales people excellent sales roles. I love being back in the sales seat. Consulting with employers on what sales people they need to be successful; meeting with the best sales professionals in Canada; creating win/wins.
At 20, I hoped to retire at 25. Now, in my mid-thirties, I hope I never have to retire.

For the love of sales!