Orchard Benefits specializes in helping startups and fast-growing companies get the right benefits coverage to meet their budgets and the needs of their employees.

Benefits is all we do, which means we have the experience, expertise and insight to get the coverage that works for you – whether your company is embracing benefits for the first time or looking to change an existing plan.

The way we work is grounded in customer service and a commitment to help clients make the right choices. We engage with you on a regular basis to educate and update, rather than touching base once a year to renew your policy.

Launched in 2000, Orchard Benefits (formerly Insurance Portfolio Financial Services) began doing business with startups in 2010 after realizing their insurance needs were unique, and needed someone who knew the challenges that the companies faced. We now work with dozens of startups, as well as startup organizations such as OneEleven and the DMZ.So, how did I get into the insurance industry?

You wouldn’t be surprised if I said through tech, would you?

From 1995-1997, I worked for Applied Systems, the largest software provider to insurance brokers and agent .

In early ’97, I made the switch to the insurance brokerage side, and started working for Insurance Portfolio Inc., a brokerage that offers commercial, home, and auto insurance. In 2001, I decided to start Insurance Portfolio Financial Services Inc. (IPFS).

By 2009, IPFS’ focus had shifted from life insurance to specializing in employee benefits plans. And that’s when the “ah-ha” moment happened. Technology has always been in my life so why not marry my love for tech with employee benefits? Since ’09, I have worked with dozens startups in the GTA. I’ve also given employee talks at Ryerson’s Startup School, OneEleven, and Extreme Startups. And, I’m an advisor at the Ryerson Digital Medial Zone (DMZ).

Orchard Benefits represents the latest step in this process, and I’m excited for what this new decade will bring.


Check what our clients say about us

"Chris provides a friendly, insightful and pragmatic approach to establishing employee benefits in growing companies. He has been responsive and helpful through the process developing an excellent package of benefits for our team."

Dan Holowack


"We are very happy with Insurance Portfolio! Chris Gory is extremely helpful, whenever I have a question, he responds right away. Chris never hesitates to come by our office to review documents with me and he always strives to find us the best options."

Hailey Adams


"I consider Chris a part of our team at Design Cofounders– his proactive efforts in our people and company's best interests is something that everyone in professional services should emulate."

Mustefa Jo’shen

Design Cofounders