Our Leadership

Chris Heard

CEO of Olive

Heather Stevens

VP of Product

Casey Baldin

Head of Customer Success

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Chris Heard

CEO of Olive

CEO & Co-founder Chris Heard started his entrepreneurial journey in his home country of England when he launched a portable cocktail bartending service called Bars in Action. This gave him an itch for starting companies, and also won him a Guinness World Record. After a brief stint in insurance sales during the 2009 financial crisis, Chris and his wife set sail for new pastures in Vancouver, Canada. Here, Chris got his first taste of the North American tech industry and he was instantly hooked.

Helping to grow local startup Mobify as an early sales hire, Chris fell in love with tech and started to hone his sales skills. Moving up the ladder from BDR to Sales Director, he quickly realized the process of evaluating technology decisions was not only lengthy and manual but also prone to bias. His ability to use this bias to the favour of his company really struck a nerve.

He was now seeing some of the darker side of sales. In one instance, Chris convinced a large organization to purchase his technology despite the fact that they weren’t a good fit for the company’s needs. This didn’t sit well with him, and it wasn’t the only time that the technology he was selling wasn’t the ideal fit for the company.


Dan Harrison

Dan Harrison

Co-Founder of Olive

To take a page from Henry Hill, “As far back as he can remember, Dan always wanted to change the world with computers”. Growing up in the semi-rural outskirts of Vancouver, Canada, there wasn’t much to do besides read, build forts, and tinker with computers. Born at just the right time to watch the growth of the internet first hand, Dan directed his life from an early age to one day have a startup of his own.

Dan spent much of his early adult life learning the trade of cabinet refinishing, which lead to his first entrepreneurial journey, taking over the company so he could continue to pay for his university classes.

With nearly 10 years behind him working directly with clients, and with a newly minted CS degree, he joined a local startup, Mobify, as a Sales Engineer. This unique role was a perfect blend of tech and customer service, and allowed Dan to grow his experience across multiple disciplines. It was also at Mobify where Dan met Chris.

After working in a number of technical sales roles, Dan noticed himself drifting from that one principle that brought him the most happiness through life: “Be of service to others” . He pulled the plug and followed his dreams, joining Chris to start Olive. Each day since has brought Dan the same excitement he felt as a little tinkerer, as he can help drive the creation of something of value and be of service to others.

Jackie DiMonte

Jackie DiMonte

Partner at Chicago Ventures

Prior to joining Chicago Ventures, Jackie was a principal at Hyde Park Venture Partners, working with portfolio companies such as RoadSync, Podchaser, Fixer, FactoryFix, and PartySlate. Before that, she worked at Silver Spring Networks (now Itron), an IoT company for critical infrastructure, driving development and pilot projects for emerging smart city technology.

Jackie began her career as a consultant at Accenture in the Business & Technology practice, focused on ERP (enterprise resource planning) software and SaaS enablement projects.

She is also a member of the Board of Directors for Starting Block Madison and Chicago: Blend and a Venture Partner at Republic. Jackie holds a B.S. with honors in General Engineering from the University of Illinois at Urbana-Champaign and an MBA with honors from the University of Chicago Booth School of Business.