Calvin Ho

Early in Greenline’s development, we had the opportunity to respond to a government Request for Proposal; an open bid to replace a province’s cannabis retail POS and inventory system. This would have been our first attempt at landing a large enterprise client.

At the time, most of our customers operated between one and five retail locations, with only a few profitable outliers. We referred to these mid sized retailers as our power users. Listening to them gave us a clear product roadmap and allowed us to grow alongside their needs. This approach had worked well for several years. Still, the RFP was tempting. Winning it would have marked a significant shift toward a much larger market and given us much credibility.

We committed heavily to the bid. Over several months, we developed a detailed plan to replace the province’s existing system and ensure a smooth, low-stress rollout. Our engineering and customer success teams confirmed it was feasible. We worked quickly to address the pain points the province faced with their current software. After several rounds of proposals, the contract was awarded to a larger provider.

In hindsight, we should not have invested so much time and energy. We poured resources into understanding enterprise requirements like SOC 2 compliance. But all of our revenue at the time came from small and mid-sized private retailers who did not care about those things. And we knew this.

We knew because we already had a growing base of power users. They were encountering operational challenges like managing staff access across multiple locations and coordinating purchase orders with central distributors. These were problems we expected larger businesses to face. Solving them was key to retention and growth.

Looking back, pursuing the RFP was not the right decision. I should have pushed for our limited resources to be focused on features already on our product roadmap; features we already knew would bring real value to our current and future customers.

To be fair, the experience did give us valuable insight. It helped us clarify the requirements our product would need to meet in order to serve larger enterprise clients down the line. But we could have saved months of time and effort if we had simply asked the right question from the start:

“Would the people I’m trying to serve care about this?”