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Head of Product and Engineering and Co-founder at Jasper

Hear about tech entrepreneur Ollie's transition from the digital agency space into building a really exciting tech business.

This "Ask Me Anything" career chat with Matchstiq Co-founder Greg Denton, will explore working at the now acquired digital agency, Little Giant with Jasper co-founder Mark Hurley.

Having teamed up with Mark again as well as another Co-founder also called Mark, Ollie shares why he is excited about what he and the team are building at Jasper and is open to sharing insight into any part of that career journey to date.

About the Speaker


Ollie Shaw profile image

Ollie Shaw

Ollie, Head of Technology at Jasper has packed a lot into his career at young age. A self confessed computer geek as a teenager, Ollie has married that passion for computers with a sharp knack for solving business challenges, as well as managing people. His passion for what he and team are developing at Jasper is clear to anyone that comes into contact with him and he is excited to help others on their career journey.

AMA Recap

Career Insights

  • Developing your soft communications skills can give your career a major boost, even if you don’t decide to go down a path that requires leadership or management. Ollie recommends reading Management books (WHAT WERE THEY?) that can help give you an appreciation of the broader considerations in a business.
  • Time and capacity management is an important thing to hone early on in your career. There is a balance between being eager and putting your hand up for more work, against being able to actually deliver that work on time and to the quality required. Ollie’s advice is to be honest and upfront early if you know that you are not going to make a delivery timeline and to not be afraid to ask for help.
  • Life is too short to not be working somewhere that you feel connected to. Spend time prioritising what elements of work will make you excited about coming back every Monday and that often means putting that ahead of money.

Job Seeker Tips

  • Showing a passion for your craft through side projects is something that Ollie really looks for when assessing candidates for roles.
  • Aside from submitting a CV, a cover letter/email demonstrating why you are interested in the company you are applying for is critical. Show that you have thought about the “why” you want to work there and what you think you can bring to the role. That will always capture his attention.

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