The CEO’s Playbook For Growth In An Uncertain Economy
April 29, 2025
What does it take to successfully transition to the role of a CEO? Lean into your strengths—but accept your weaknesses and build a solid team to support you, says Roland Gossage.
Gossage is CEO of GroupBy, a Toronto-based company that provides AI-powered search and recommendation capabilities to B2C and B2B ecommerce platforms. Prior to his career in software, Gossage was a member of the Royal Canadian Armored Corps, which inspired him to establish the Roland Gossage Foundation in 2019. The nonprofit assists veterans transitioning to civilian life, helping them reskill into in-demand technology jobs to find more creative and rewarding career opportunities.
He shares his journey to becoming a leader across a variety of fronts.
Following my retirement from the Canadian Armed Forces in the early 2000s, I felt pigeonholed into positions aligned with my experience in the service, such as private security. And while my skills were very transferable in those roles, I personally didn’t find them very rewarding. Like myself, many people have post-military aspirations that don’t involve the core work of the armed forces.
I was lucky enough to get into technology, where I have spent the past 20-plus years. It’s the kind of advantageous, fast-paced market that veterans are seeking. I wanted to offer a path forward for other soldiers who might not have the knowledge or connections to look beyond security and civic positions.
I started the Roland Gossage Foundation with our Soldiers and Tech program, a 12-week full-stack web development boot camp for veterans with little or no computer science experience. We have since expanded to include data science, data analytics and cyber security programs as we continue to foster skills for high-demanding and high-paying jobs.
Most recently, we launched a new initiative called Soldiers in the Arts, where we place veterans on movie and TV sets to teach them the trade and ultimately start their careers in the industry.
Through dedicated instruction, wellness support and career services, we aim to ensure that veterans have the necessary resources and guidance to succeed in their civilian careers and overcome this transition’s difficulties.
At GroupBy, we’re revolutionizing the ecommerce experience by bringing next-gen search and product discovery to some of the world’s biggest retailers and distributors. As an industry veteran and leader in retail and technology, I believe in the power of sharing experiences, insights and views on the latest trends. The Forbes Tech Council and Retail Wire BrainTrust are platforms that allow me to do just that.
The Forbes Tech Council enables me to publish byline articles on the future of retail and the innovations modernizing the ecommerce experience, such as generative AI, AI-first search and data enrichment. At the same time, BrainTrust allows me to provide expert commentary on trending news stories.
The platforms also serve as excellent networking channels, connecting me with a larger community of professionals. For example, earlier this year, I participated on a panel with a fellow BrainTrust member to discuss how AI is driving the future of product discovery and merchandising.
Transitioning into the CEO role brings new tasks and responsibilities. I advise rising leaders to identify and lean into their strengths, while at the same time accepting their weaknesses. It’s natural for people to gravitate towards the areas in which they’re the most confident and comfortable. However, it’s how they navigate other aspects of the role that differentiates good leaders from really great ones.
If a person excels in overall vision, sales and marketing and less in finance and operations, they need to be honest with themselves about where their potential weaknesses lie and build a solid team to support them in those areas.
Remember, you can’t be everything to everyone, but you are responsible for getting the job done. To succeed, you must be comfortable relying on those who support you. You may be the leader, but you’re still part of a team. It’s this collective effort that leads to success, and that’s what makes leadership so inspiring and motivating.
Chief Executive Group exists to improve the performance of U.S. CEOs, senior executives and public-company directors, helping you grow your companies, build your communities and strengthen society. Learn more at chiefexecutivegroup.com.
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1:00 - 5:00 pm
Over 70% of Executives Surveyed Agree: Many Strategic Planning Efforts Lack Systematic Approach Tips for Enhancing Your Strategic Planning Process
Executives expressed frustration with their current strategic planning process. Issues include:
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2:00 - 5:00 pm
Female leaders face the same issues all leaders do, but they often face additional challenges too. In this peer session, we will facilitate a discussion of best practices and how to overcome common barriers to help women leaders be more effective within and outside their organizations.
Limited space available.
10:30 - 5:00 pm
General’s Retreat at Hermitage Golf Course
Sponsored by UBS
General’s Retreat, built in 1986 with architect Gary Roger Baird, has been voted the “Best Golf Course in Nashville” and is a “must play” when visiting the Nashville, Tennessee area. With the beautiful setting along the Cumberland River, golfers of all capabilities will thoroughly enjoy the golf, scenery and hospitality.
The golf outing fee includes transportation to and from the hotel, greens/cart fees, use of practice facilities, and boxed lunch. The bus will leave the hotel at 10:30 am for a noon shotgun start and return to the hotel after the cocktail reception following the completion of the round.