Top Takeaways from High Alpha’s Leadership Flight School

Many variables make up our days. Markets change. Deals are made. Releases go live. As unpredictable as all of the above can be, there is always a stalwart pillar in our day — leaders.

Leaders are those who guide us through ambiguity and ever-changing landscapes. Leaders in startups often wrestle with nuances like how do you lead when the vision is ever changing? How do you motivate a team to hit milestones? When you’re always in a sprint mode, how do you dedicate time to people managing and developing your talent?

On October 10th, High Alpha hosted its first Leadership Flight School and for a full day, leaders from across the High Alpha portfolio gathered to discuss our most important assets — our people.

The day was full of fantastic learning and conversation. Here are 3 top takeaways from the day:

Expect and Inspect

Scott Dorsey, Managing Partner at High Alpha, and Julia Kauffman, VP of Human Resources started out the day with a Fireside chat. Scott spoke about his own leadership philosophy and his experience being a leader in SaaS companies.

  • Expect — model the behavior you would expect from others.
  • Inspect — know yourself and push to learn your strengths and weaknesses.
  • Partner with HR as a strategic player. Ensure you’re thinking of your talent just as you would any other resource.
“We are in the business of software. People are our competitive leverage.”

Invest in Talent

HR Leadership from across High Alpha’s portfolio shared ideas on how best to attract, retain, and manage talent in a high growth environment.

  • Someone can always earn more. Startups have so many different value propositions compared to other companies. Ability to impact, grow and learn directly with leadership — there are many advantages of working at a startup. Often, we may not be paying top market yet, but think holistically about the advantages you have to offer and remember that’s part of your compensation.
  • Everyone is a recruiter. Open roles affect startups more acutely because of the lack of bandwidth in the company. In the High Alpha portfolio, we’re lucky to have HR support from Day 1 of launching a company, but when it comes to finding the right person for the role, remind your team to put on their recruiting hats. They should reach out to their network and be involved in the hiring process to ensure you select the right talent.
  • Pause for development. When you’re moving fast, it can be difficult to remember to pause to check in with your team. Are they developing how they would like? Have you talked to them about performance? Incorporating continuous feedback process (and documenting it) can ensure your team is developing and engaged.

Do Better Work

Max Yoder, CEO, and co-founder of Lessonly stopped by to share some of his learnings as a leader that will be featured in his upcoming book “Do Better Work.” Max challenged the group to think through these questions.

  • What do I celebrate? Acknowledging team members who hit sales quotas is easy, but what other behaviors do you want to reward? Would you want to reward the employee who stepped up so their coworker can have a restful vacation? Call it out and recognize the unsung behaviors that make your team better.
  • What do I do? Max reiterated that if you want to see it, be it. Team members will notice what you do. Call out your own mistakes and take ownership. Modeling this behavior encourages your team to feel comfortable doing it as well.
  • Can I do it better 1% of the time? It’s easy to get caught up and feel overwhelmed when it comes to making a change in work habits. Just doing things better 1% of the time are small changes that can make a difference. All of these things can feel aspirational, but the more you do it, the better.

A common theme throughout the entire day was recognizing the talent we have in our portfolio. It’s what allows us to do move fast and accomplish tremendous milestones.

Hosting a Leadership Flight school is one way we’re recognizing and developing our talent and it will be amazing to see how this ripples out into the broader portfolio.

Thank you for everyone who attended and we hope to see you next year.


High Alpha is a venture studio pioneering a new model for entrepreneurship that unites company building and venture capital. To learn more, visit highalpha.com or subscribe to our newsletter.