The technology business is often branded as a men’s game, and from my experience building and leading technology businesses, I understand why. There are a lot more men than women in tech. Whenever we have an opening for a software developer role, the resumes we receive skew overwhelmingly male. At the senior most levels, the CEOs who have become the faces of technology - Bill Gates, Steve Job, Mark Zuckerberg, Jeff Bezos, Tim Cook (or is Tim Apple?)... are male.

With that said, I have gotten to know many great female tech entrepreneurs and female leaders greatly impacting the world of technology from both my entrepreneurial career and through my media endeavors. Two great female leaders in technology are Hilary Gosher and Traci Inglis. They are not necessarily household names, but they are doing big things. Hilary is a Managing Director at Insight Venture Partners, a leading venture capital firm. Hilary founded the team there that has invested in more than 200 software and Internet companies, including Drillinginfo, Turnitin, Alteryx, Cvent, Mimecast, Medidata Solutions, Shutterstock, DataSift, Fuze, Evestment, ECI Solutions, OverDrive, Primavera, Netsmart Technologies, TeamViewer, Shunra and Vertafore. Traci is the President of JustFab and Shoedazzle.

Hilary and Traci are among the many top leaders I have had the opportunity to interview in my Lessons In Leadership series in Thrive Global. Here are some excerpts from the interviews with Hilary and Traci:

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?

Traci: I’m going to give you 5. I know, my Type-A overachiever is showing… a. Assume positive intent. A lot of workplace (or social group) conflict is bred from someone reading text on a screen and assuming an emotion was connected to it that may not have ever been. If you assume negative intent, you may read something into it that wasn’t there and then respond with a nastygram that wasn’t warranted. b. Always know where you want to be in 5 years and figure out what you need to learn, accomplish, or change in order to get there. Take a course, volunteer to take a new project at work, ask to have coffee with a senior exec in that area – whatever you do, don’t sit there waiting for it to fall into your lap (spoiler alert: that isn’t going to happen). c. Be your own champion. A mentor along the way told me to always have a plan for what to say to various senior management members if you run into them at the water cooler. Run into the CFO? Share the big news that you came in under budget on the big project. Run into the CEO? Share that your latest launch is beating plan. Keep a running list in your head for those moments of opportunity to subtly and organically champion your wins. d. Listen to your customers. This is the key to a successful business in ANY industry. In my past, we spent a lot of time in the stores talking to customers. At JustFab & Shoedazzle, we don’t have stores so we started having dinner with our customers – once a month we invite them to the office to hang out with us and tell us what we could do better. I can attribute millions in revenue from ideas that have come from those dinners… actually one idea is now driving nearly $20M annually now. e. Always go beyond. When I was growing up, my dad used to always challenge me with “Have you done everything you could do? Can you think of one more thing you could do to achieve your goal?” So think of that one thing, and then do it.

Hilary: 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: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Traci: When it comes to the leaders on my team, I equally value functional expertise and leadership skills. Functional skills are easier to assess than leadership skills, but it’s the latter that can have a much bigger impact on a team. Having leaders in place that bring out the best in their people is important to me. I try to foster an environment where people feel safe to challenge ideas and bring new ways of approaching a problem.

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 failures, setbacks or challenges have been most instrumental to your growth?

Traci: A lot of naysayers have fueled my ambition, and my ambition fueled me to be curious, innovative, and hard-working. In terms of projects that haven’t worked out, I have a strong appetite for testing, so I’ve seen as many failures as wins – I like to quote Thomas Edison when we have a test that doesn’t win – “Many of life’s failures are people who did not realize how close they were to success when they gave up.”- you have to just keep going after it.

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.

You can read both interviews in full at and

Adam Mendler