Tips From The Top: One On One With Hilary Gosher

I spoke to Hilary Gosher, Managing Director at Insight Venture Partners, about her best advice

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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.

Adam: What do you look for when considering a private equity investment?

Hilary: Private equity at Insight isn’t dissimilar to venture: we look for large market opportunities and good products that can support continued organic growth. Additionally, we look for the ability to do add-on acquisitions and consolidation. M&A is an important component of successful PE outcomes, both finding the targets, and integrating them to realize synergies. When we make a PE investment, we have a unique advantage in our strong growth-oriented sourcing engine. Often, even prior to deal close, we have deep relationships with target companies that we can integrate to drive inorganic growth.

Adam: What are your three best tips applicable to entrepreneurs and executives?


1) Hire A-players – be honest about your strengths and surround yourself with people that can complement your capability gaps. Don’t be afraid to hire people who are smarter and better than you, it increases the likelihood of your company’s success, and reflects well on you.

2) Focus on Go-to Market – companies initially grow through product-centricity. The key to scaling is developing the capacity to market and sell product. This change usually necessitates hiring strong marketing and sales leaders.

3) Stop doing – focus on strategy and company direction, let others execute. If you don’t take time to know where you’re going, it’s easy to get bogged down and stray off course. If you’re a sales-focused CEO/founder, stop selling, rather, build a sales motion that can scale. If you’re a developer-focused CEO/founder, stop coding and focus on product direction and customer value. Knowing when to let go is a key harbinger of success.

Adam: What do you look for when evaluating leaders? How can leaders and aspiring leaders take their leadership skills to the next level?

Hilary: The best leaders I’ve worked with are self-aware. A company’s business model is iterative and based on objective market feedback, and so is leadership. The best leaders are those who work on themselves objectively, just like any product.

I recently began to work with an executive coach who gathered 360-degree feedback from the people I work with. It was eye-opening to see how others viewed my communication style, my strengths and impact on our business. We developed a list of actions and behaviors that would make me more effective and I set a plan to implement them.

Adam: What is the single best piece of advice you have ever received?

Hilary: When I first moved to New York City, I introduced myself to a doctor. Her advice amused me and stuck with me: if you want to lead a long and healthy life, remember three things, “always wear a seatbelt in taxi cabs,” “stop eating when you’re full,” and “get enough sleep.” Seems like these are good maxims to employ.

​Adam: What is one thing everyone should be doing to pay it forward?

Hilary: Cultivate a sense of gratitude. If we realize how lucky we are to be living in a century where connectedness, opportunity, knowledge, freedom, choice is so available to us, we will be more likely to show empathy for others and willingness to lend a hand: whether to an aspiring graduate, entrepreneur, or person on the subway.

Adam: What are your hobbies/ interests and how have they shaped you?

Hilary: Mentoring has been a passion since I began teaching Entrepreneurship eight years ago at NYU business school. I’d like to see more women have stellar careers in VC and investing. To support this goal, I co-founded Parity Partners to formalize and scale mentoring for women – today more than 500 women are in the program in San Francisco, London, New York and LA. The program includes leadership development skills, career advice and mentoring. It’s a model that can work in a company, or across an industry.

Adam: Is there anything else you would like to share?

Hilary: Venture Capital is a career that combines curiosity, expertise, problem solving, and intuition. It takes guts and determination to break into the industry, but it’s a satisfying and interesting career for women. I hope more women enter the industry because doing so has the potential to change business: not only which businesses get funded, but the leadership composition of the businesses they fund. 

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