The Olive Branch Between Technology Buyers and Sellers

Technology buyers and sellers are at odds, but they don't need to be! Olive was founded to transform and streamline the technology evaluation process.

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The Story of Olive

In 2017, Olive’s co-founder Chris Heard was waiting for yet another flight at a quiet airport bar, having just met his 30th stakeholder. A veteran in enterprise software sales, he spent months with countless meetings for just one organization, and still they couldn’t make up their minds. Working with his internal champion, Chris of course made every effort to influence the decision in his company's favor, but nine months into the sales cycle, he realized his solution may not actually be the right fit for this customer. 

"This is not how companies should buy and sell software."

Over the years Chris noticed a rapid increase in the software selection process being controlled by the sales teams. Buyers had become tired of complex buying processes and wanted to simplify their buying process so they could innovate faster. Unfortunately in simplifying this process, they handed control of the buying process to sales people. This resulted in vendors with the best sales teams winning their business, while the vendors with the ideal solution went unnoticed.

Looking at the tools available for vendors Vs. sales people, it was obvious that the scales were heavily weighted in favour of the vendor. Olive would change that. Long time colleague (and now co-founder of Olive) Dan Harrison agreed. They ideated on how to develop a solution that would benefit buyers and sellers alike, enabling visibility into company-wide needs, automating tedious tasks, reducing time, effort, risk and cost of evaluations, and retiring the traditional RFP process, #RIPRFP!

The Solution? A technology evaluation platform for IT consultants and IT leaders that's efficient and free of bias, revolutionizing the vendor selection process.

In 2018 Olive was born, and Chris and Dan set to work on reimagining the current process of technology evaluation to remove the inefficiencies and bias from the buying process. 

Olive would be a tool made for IT consultants an buyers to find solutions that drive innovation. With our early customers, we learned that there were some major pain points in the software procurement process that we could solve immediately;

Save Time, Reduce Effort, and Minimize the Cost of Technology Evaluations

By enabling visibility into companywide needs, and transparency from vendors, we are innovating the RFP process. No more spreadsheets, no more googling for RFP templates! Save time, effort and reduce the cost of technology evaluations by streamlining your process in the Olive Platform.

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Make the Perfect Buyer Technology Match,
Every Time

Extending this transparency into the process of working with solution providers, we connect sellers to buyers based on the buyer’s needs. Whether it’s HCM, CRM, ERP, LMS, POS, or any other type of software or technology solution, Olive helps determine the best fit based on unbiased data, so you can be confident you will make the best choice.

Our Core Values

No Bias - Facts First

We will not allow ourselves to be biased. We make our decisions based on facts, not opinions. Rationale is what makes Olive valuable.

Customer Obsessed

We make sure the collective needs of our customers is paramount in all of our decisions, and our product.

One Impossible Thing at a Time

Everything we do is a mission impossible. Only by focusing on one impossible thing at a time can we truly achieve.

The Board

Chris Heard

Co-Founder 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.

This culture of bias and Chris’ ability to influence decision criteria, was the catalyst for the conception of Olive.

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

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.

“Olive gives us confidence in our decisions, helping us to cast a much wider net, quickly narrow down our options, and cut costs. In one example, we found a vendor that was 80% less expensive than we planned for, plus the implementation and execution went great.”
Trevor Fitzgerald - VP IT @ WKS
“I have had projects take 3 years from requirements to implementation; Olive saves me months of effort”
Tariq Chaudhry - A&W Canada
“Working with Olive gave me valuable insights into the client’s needs and expectations. The process played a key role towards the client’s purchasing decision”
“Balancing stakeholder requirements when evaluating technology options is an eternal pain point. Olive have really built a solution that I can count on to help me deliver value to our teams. No industry is untouched by digital transformation. Immediately and in the future, Olive have an opportunity to become an indispensable product for anyone tasked with IT procurement.”
Sean thompson - freddies frozen custard and steakburgers
“With Olive we were able to find the best fit solution for our needs much faster and with less effort than ever before”
“With Olive we were able to find the best fit solution for our needs much faster and with less effort than ever before”
“With Olive we were able to find the best fit solution for our needs much faster and with less effort than ever before”
“With Olive we were able to find the best fit solution for our needs much faster and with less effort than ever before”
“With Olive we were able to find the best fit solution for our needs much faster and with less effort than ever before”
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