Jeff Dennis


With over 30 years’ experience as a lawyer and serial entrepreneur, Jeff has become the “go to guy” and trusted advisor to the CEOs of fast growth companies.

Trusted Advisor

Emerging tech companies and fast growth businesses often are unable to afford full time members of their team to fill some of the most important strategic roles in the business. Jeff works as a paid advisor and an advisory board member – both cost-effective ways for companies to enhance their team with A Players.

Jeff has worked one-on-one with leaders, sharing his experience and his global network. He has also worked with companies and CEOs to build out a first-class advisory board, which he often chairs.

He is known for his “tough love” approach. He challenges his clients to reach the company’s and the leader’s full potential, asking the tough questions and holding them accountable as they work together towards the company’s goals.

Jeff generally works with his clients on a fixed fee monthly retainer basis in order to provide certainty and transparency as to the cost involved in working with him. His motto is “no surprises”!

Strategic Planning

Jeff has worked with boards and senior level teams as a facilitator of strategic planning sessions. He challenges his clients to develop comprehensive and reality based strategic plans and financial projections.

Restructuring Advisor

As any entrepreneur knows, each set back is a learning experience and the ability to adapt and pivot is a necessary life skill for any leader. Jeff has acted in an interim capacity as Chief Restructuring Officer on several investments. He successfully navigated the restructuring of operations and the sale of non-core assets. In one particularly difficult situation, he was able to lead the completion of construction and the sale of a 10 MW wind power facility over a 24-month period.

Negotiation Coach

Jeff’s extensive corporate finance and M&A experience has enabled him to work on both bilateral and multi-party negotiations. As an expert in the art of negotiation, Jeff is able to advise his clients on their negotiation strategy and assist them in achieving better outcomes.

Pitch Coach

Jeff has raised over $2 Billion over his career for a variety of projects and industries. He has also been an investor and understands the perspective of angels, family offices, venture capital, private equity and public markets investors. For many years, he has chaired TiEQuest, Canada’s largest annual pitch competition and has seen thousands of pitches.

He critiques his clients’ pitch decks, financial projections, valuation and presentation and helps them understand how to pitch to each type of investor.


Jeff has extensive experience as a director of public, private and non-profit organizations. He completed the Directors’ Education Program of the Institute of Corporate Directors and the Rotman School of Business at the University of Toronto and has been awarded the ICD.D designation.

Jeff has experience as a board chair, secretary and has participated on a variety of board committees.

M&A and Corporate Finance Advisory

Jeff is a deal maker. Throughout his career, he has structured and completed various types of financings – angel, family office, venture capital, private equity and public venture capital.

He has also bought and sold businesses of various sizes and industries. The purchase or sale of a business is typically one of the most important and largest transactions in a person’s life. It is critical to surround yourself with a trusted advisor.

He understands the perspective of both the entrepreneur and investor, having been on both sides during his career. He has acted as both advisor and principal, bringing an important perspective to any transaction.

Jeff has extensive experience with private equity, venture capital, angel investors and family offices. He has worked with all forms of corporate financings, including SAFEs, convertible debt, mezzanine financing, bank debt and equity. He has been involved in over $2 Billion of financing during his career.

Public Venture Capital Advisory

Jeff has been involved in taking companies public on the Toronto Venture Exchange (TSXV), both as principal and as legal advisor. He is familiar with the TSXV’s Capital Pool Company Program (CPC), having led the creation of 2 CPCs and the completion of their Qualifying Transactions.


You’d want Jeff on your side of the court as a founder. And as a female, visible minority founder, it’s important to note that Jeff has treated me fairly and equal to my peers. Jeff has saved me from a particularly bad deal and I’m grateful to have had his guidance during that time. I strongly recommend Jeff!

Arwina Mogul, Founder,

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