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In The Trenches


This site exists for one reason: To improve the personal and professional lives of Entrepreneurs and CEOs running Small and Medium Sized Businesses (SMBs)


Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Personally and professionally, we face both challenges and opportunities that few others can relate to. Though many understand the rewards of company leadership – like compensation, decision making authority, and independence – few understand the sometimes arduous journey that’s required to get (and stay) there.

As both a CEO and Entrepreneur, I have had many successes and (many more) failures, each of which has imparted upon me lessons that can’t be learned in any textbook or classroom. Despite the fact that countless leaders before me have learned similar lessons through their own experiences, I’ve found that many of these lessons never get communicated to, and utilized by, other leaders who may be most in need of them.

That’s why I created In The Trenches. My hope is that this site plays a small role in improving both your personal and professional life through learning from my own successes and failures in leading a small to medium sized company.


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Migrating Your Software Company from On-Premise to SaaS: Part 1

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Understanding and Managing The Psychological Toll of Being an Entrepreneur or CEO

My Guest Dr. Eliana Cohen is an entrepreneur and Clinical Psychologist who runs her own practice, integrating performance psychology, strategy, emotional intelligence, and knowledge of neuroplasticity and the brain to serve her various clients. She has worked with countless entrepreneurs,Continue reading “Understanding and Managing The Psychological Toll of Being an Entrepreneur or CEO”

CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?

My Guest Warren Coughlin is both an entrepreneur and business coach, having worked directly with countless Entrepreneurs and CEOs for upwards of 20 years. His coaching practice focuses not only on the business itself, but also on the entrepreneur atContinue reading “CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?”

The Private Equity Perspective on Acquiring, Operating and Selling Software Companies

My Guest Jordan Bettman is a Partner and Co-founder of Radian Capital, a New York-based Private Equity firm focused on B2B software and technology-enabled services businesses. Radian has ~$500 million of assets under management, and is now investing out ofContinue reading “The Private Equity Perspective on Acquiring, Operating and Selling Software Companies”

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About Your Author

Steve Divitkos is the former CEO of Microdea, a document management and workflow automation software company serving the transportation and logistics industry. Steve acquired the business from its original founders in 2014, and successfully sold the company to a strategic acquirer in 2020 after having served as its CEO for approximately seven years. During Steve’s tenure as CEO, Microdea’s equity value quadrupled, providing his investors with a 20% compounded annual return on their original investment. In his first 5 years as CEO, Steve doubled company revenue, achieving a ~15% compound annual growth rate, leading to Microdea being named as one of Canada’s fastest growing businesses for four consecutive years between 2014 – 2017. Since that point, he led the company’s transformation towards a subscription revenue model, growing revenue from recurring sources from ~40% of total revenue in 2014 to ~80% in 2020. He helped grow the company’s customer base to include 80% of Canada’s largest trucking companies, and one third of North America’s largest logistics companies. Under his leadership Microdea was ranked as one of Canada’s best places to work for 4 consecutive years between 2017 – 2020, when the company was named as the 46th best place to work in Canada for all companies with fewer than 100 employees. Upon his departure from the company in 2020, Steve had a 100% CEO approval rating on glassdoor.com.

Prior to his time at Microdea, Steve served as the Founder and Managing Principal of RedLeaf Management Partners, a private equity firm focused on acquiring small to medium sized private Canadian businesses. Prior to that, Steve worked in both Private Equity and Private Debt at the Canada Pension Plan Investment Board (CPPIB), the $456B independent investment management organization charged with investing the assets of Canada’s national pension fund, supporting over 20 million working Canadians.

Steve received his MBA from Harvard Business School, and his BBA from Wilfrid Laurier University, where he graduated with distinction. Steve lives with his wife Krista & daughter Mila in Toronto, Ontario, Canada.