An Interview with sales leader Scott Leese

Scott Leese is a 6x sales leader, founder, 3x best-selling author, and a strategic advisor to many of the top sales tech companies in the world. We sat down with him to understand how he started out, what it’s like leading sales teams at rapidly growing tech companies, and how he became so popular on LinkedIn.

Q: Tell us about your career journey. How did you end up where you are now?

A: I got started late in my career. I was 27 when I got my first sales job. I knew I wanted to go into sales leadership really quickly and once I had been a sales leader a few times over I realized I wanted to do my own thing. So I focused on diversification of income streams and building a w2 career at the same time, so when I cut the w2 cord I wasn’t starting from scratch.

Q: Part of what you do is help companies scale their sales teams and revenue. Can you explain some of the things you advise companies to do that have the most impact?

A: Most startups lack a structured sales motion. They don't have a playbook, a process, or a strategy. They run out of momentum just winging it because winging it doesn't scale. So I try to help folks realize the work they do in the early days should already be optimizing for scale.

Q: Before going off on your own, you successfully led multiple technology sales teams to rapid growth. What do you believe made you so successful?

A: I spent 4 yrs in the hospital in my 20s after having been a 2 sport athlete in college. I was already hyper competitive but I gained an extreme sense of urgency and appreciation for the limited number of opportunities we have in this world. So I just think I care more than most people. I did my best to surround myself with people who were tired of how things were and were at a place in their life where they were ready and willing to do whatever it takes to change their life in a meaningful way. When you do that at some level of scale, beautiful things happen. 

Q: What was your biggest failure in your sales career?

A: Like most people, I have a blip on my resume. I didn't vet the company, the product or the founder well enough. I took the check and was over-confident that I would be able to make it work. can’t turn water into wine [shocking, I know]. 

Q: One thing that many sales reps struggle with is staying motivated and consistent. Do you have any advice that can help sales reps with these things? 

A: I actually cannot relate to that. Because of the struggles I've had, I have no idea how people are not motivated. It comes naturally for me to keep doing the things that are working rather than tinkering or trying to do less. I focus on the outcomes, not how I get there, and I take action before I allow my head to overthink things.

Q: You have a sizable LinkedIn following (90K+ followers). How do you differentiate yourself from the thousands of other sales influencers out there and actually add value to your audience? 

A: I really don't know how to answer that, nor do I think I should. I think you should ask the people who read my content what I do that stands out. All I know is that I try to be the same person I am in real life as in my content, and I genuinely try to help as many people every day as I can. I stay accessible and I try to tell people what I think they need to hear, not what they wanna hear.

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