Tips From The Top: One On One With Hilary Gosher | Blog | Insight Venture Partners
Strategy and M&A

Tips From The Top: One On One With Hilary Gosher

by Insight Onsite

Interview between Hilary Gosher, Managing Director at Insight Venture Partners, and Adam Mendler, CEO of The Veloz Group. 

Adam: Thanks again for taking the time to share your story and your advice. First things first, though, I am sure readers would love to learn more about you. What is something about you that would surprise people?

Hilary: I am obsessed with great stories, as a result, I’m a huge podcast fan. Podcasts give me access to a world of knowledge that is both inspiring and always on tap. I have tens of podcasts on my phone and I listen to them whenever I have a free moment: in the subway, walking to work, on the runway before take-off; I even have Amazon Alexa play them for me when I’m home.

Adam: How did you get here? ​What failures, setbacks or challenges have been most instrumental to your growth?

Hilary: One of the ironies of a career is the skills you develop as a junior person – those that get you recognized and help build expertise, are not the same skills needed for senior leadership. Execution capability is less important for leadership than empathy, listening skills, strategy and vision. I’ve had to learn that I can no longer touch or engage in every activity; I risk holding up progress. My role is to provide direction and stand back to let the team do their job. Paradoxically, learning to lead, rather than do, has been a challenging transition.

Adam: What do you look for when deciding whether to make an investment in an early stage company?

Hilary: Product-market fit is the crux of future potential. If a founder is solving a real customer pain point and has an easy-to-use product about which customers are fanatical, then other metrics will speak for themselves: subscribers and revenue will be growing, retention will be high, and word-of-mouth will yield more customers.

Insight seeks to get under the hood of the product need. While we look at key business and financial trends, a lot boils down to product-market fit. Find a tough problem, solve it for people in a way that delights them, and they will pay for it, tell their friends, and come back for more.

Also worth noting is that a large TAM (Total Addressable Market) is not necessarily sufficient. Of course we love huge TAMs. But, unless the product is highly differentiated, the ability to disrupt an incumbent may be weak. We also factor in assumptions about how much TAM is available. In some situations, despite a large TAM, too much needs to go right to achieve the kind of returns that makes the investment interesting.

To continue reading the interview, please go to Thrive Global's blog

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