ITA Spotlight: Jonathan Leaf, Area Sales Leader (Central US), AWS
Monday, November 4, 2019
Posted by: Gary Hotze
Jonathan Leaf, Area Sales Leader (Central US), Amazon Web Services
1. Chicagoan by birth or relocation?
2. If you relocated, what brought you to Chicago?
My prior company for a job promotion
3. How did you come to work with AWS?
Amazon Web Services (AWS) was looking to introduce Chicago as a new sales hub for its Territory customer segment serving the Central US.
4. What about AWS was appealing?
AWS helped to pioneer the Public Cloud market which enables businesses to innovate like never before. This combined with having the opportunity to join a company growing this quickly while introducing a new sales hub in my hometown was very appealing.
5. What other roles have you held in the industry? How did they lead you to where you are now?
I spent 18 years at my prior employer serving in jobs spanning sales, sales management, sales operations, and marketing. These different roles and experiences have allowed me to step into my role at AWS and help build and innovate.
6. Out of all the positions you've held, which one is the most interesting?
Serving as Director of Sales Operations at my prior company easily stretched me from a learning standpoint most. In that role, I was responsible for facilitating the build of the company’s financial operating plan as well as a go-to-market strategy.
7. What do you like most about what you do?
Having the opportunity to build a sales organization in my hometown with AWS, one of the world’s most recognizable and innovate companies is an honor. I love building teams and AWS has afforded me the opportunity to hire and work with wonderful people.
8. Which achievement at AWS are you most proud of?
One year ago the teams I am responsible for exclusively resided in Seattle and San Francisco. While we still have a number of teammates in those cities, we also have 25 people in Chicago as well.
9. What’s your outlook on the local tech industry?
I am bullish on tech in general as well as Chicago’s role in the industry. As big tech invests locally that will only further benefit the city. Amazon is hiring another 400 tech-centered roles in Chicago, as an example. This type of investment in parallel with a continued focus on growing the VC, Start-Up and SMB presence will mean more tech talent continues to migrate our way.
10. What do you think are the top issues facing the Illinois tech community?
Tech talent still tends to lean toward the West and East coast. This could be attributed to the coasts having critical mass through the presence of companies and VC’s with Midwest companies playing catch-up to their tech-forward as their peers. I also believe we have an opportunity to create a more diverse workforce in tech locally. Finding ways to involve more women in computer science-related roles.
11. What did you want to be when you were in kindergarten?
Professional baseball player…Without question. Still do, but now 41.
12. What is the hardest challenge that you’ve faced on your professional journey?
Finding the balance needed in my personal life to support success professionally.
13. What’s the best advice that you’ve ever received?
Tough question. Through years of leading teams, I have come to realize work needs to be purposeful in order to attract and retain talent. People are most productive when they know leadership is here to help them be successful while also taking a vested interest in their development long-term.
14. What success are you most proud of?
Likely my run at my prior company where I joined as an inside sales rep and exited 18 years later as a sales VP with responsibility for a big part of the company’s overall revenue.
15. Who has had the biggest influence on your career?
A gentleman by the name of Steve Leslie. Steve was my manager through my run in sales operations, marketing, and regional sales leadership. Steve taught me to remain cool under pressure, never letting your emotions get in the way of being able to lead teams effectively.
16. What is the one thing that keeps you up at night?
My staff as compared to the massive market opportunity that exists. We don’t have nearly the number of people needed to tell the AWS story to everyone we want to.
17. What kind of technology could you not live without?
18. What is the coolest thing you’ve developed or project you’ve worked on?
What I am doing currently is very fulfilling. Again, I was told to build a sales hub in Chicago that could scale to hundreds of people. That is underway and we are having a blast doing it.
19. If money was no object, what would your dream job be?
I really enjoy what I do. If money were no object, my dream job would still have a lot to do with building teams and helping those teams achieve what they might not think is possible.