Imran Syed on selling a business, thriving in a digital age, and ethical leadership
For the past few weeks, we have been following the journey of Imran Syed—Founder and CEO of Hatchproof (external link) —through a series of posts on LinkedIn that document his experience in the prestigious Techstars NYC Accelerator Program (external link) . From his initial hesitation to join Techstars to the intensity of Demo Day, Syed has shared his unfiltered insights into the startup world, leadership, and the future of work.
“I think exiting a company is ten times harder than even building a company,” shares Syed, a 2009 Marketing Management graduate from the Ted Rogers School of Management. After leading Instapage (external link) as CEO and successfully selling it for $65 million in 2023, he set his sights on an even greater challenge, revolutionizing workplace alignment through AI.
“I envisioned a future where Tony Stark is interacting with Jarvis,” Syed recalls. “AI has the potential to go beyond a co-pilot into an autopilot role that truly supports individuals.
That vision became Hatchproof (external link) , the first agentic behavioral AI companion for work, designed for forward-thinking companies that want smarter hiring, engaged teams, and frictionless performance. It was the rapid change of technology and its impact on business and daily life that attracted Syed to his current role. Hatchproof’s innovative approach has earned the company a spot in the Techstars NYC 2024 Accelerator Program, emphasizing its commitment to addressing employee retention challenges.
Syed’s entrepreneurial instincts have always been driven by curiosity and problem-solving. Back in 2017, Syed was promoted to Regional Vice President at Oracle Marketing Cloud (external link) . Through acquisition activities, Oracle seeks to strengthen its product offerings, accelerate innovation, meet customer demand more rapidly, and expand partner opportunities. Some featured acquisitions include Adi Insights, Cerner, and Next Technik. His time at Oracle gave firsthand experience in how large corporations strategically acquire and integrate innovative companies, a lesson that would prove invaluable when he later led and sold a company of his own.
Not long after, Syed began working for Instapage (external link) in 2020—a platform that offers world-class products that allow users to build, experiment, and optimize landing pages at scale for greater campaign results. During his time at Instapage, Syed learned that with the right approach, you can rebuild, re-energize, and lead a team to extraordinary outcomes.
After becoming CEO in 2023, he sold the company that same year—a decision that led Syed to a surprising realization.“My biggest career challenge was selling a company,” he says. “You know, I think there's a lot of startups that get created out there…very few have a happy ending and it's extremely difficult. I worked around the clock to make that deal happen.”
Syed spent the following six months researching the technology space, looking for the next big challenge. As he explored emerging trends, he became increasingly drawn to the potential of AI in transforming workplace productivity—an interest that led to the creation of Hatchproof. “It all felt so new. And even though I had managed HR functions for some time, the space was really like another pivot in my career where I spent a lot of time in MarTech and AdTech.” Ultimately, he explains that moving into the workspace of AI was very exciting.
Syed highlights that selling a business involves mourning it as it enters the next chapter of its existence. He states that as a CEO, you’re responsible for everybody—this means finding a home for all the employees that helped build the company. He concludes that in a technology-reliant community, adaptability and taking risks are skills to aid progress. “That's the role that TMU can play to help students be more adaptable to the changes of tomorrow…the more problems we can see, the better and more crystallized we can get at building solutions.”
