Top Takeaways from Product Flight School 2019

On Thursday, April 25th, we hosted the 2019 High Alpha Product Flight School. Product Flight School brought together 100+ engineers, product managers, and designers from across our portfolio to Indianapolis for a day of learning and networking hosted at the new Phoenix Theater. This Flight School was our largest Flight School event to date and featured incredible speakers from some of the largest and fastest growing SaaS companies in the country. Below are some of the top takeaways from the day:

Product-Led Growth

Blake Barlett, a Partner at OpenView Ventures, kicked the day off with a presentation on the rise of product-led growth. Blake shared examples regarding the evolution of how software is implemented and how companies like Slack and Zoom are bringing a new wave of software delivery—a single internal user in an organization organically inviting others to join the product. Why has this shift occurred? Blake shared his theory on the emergence of PLG and software delivery evolution based on the full consumerization of IT that now exists. This has forced enterprise software companies to become more aesthetically pleasing and focused on driving value as early as possible as the user is now the ultimate decision maker. Blake broke down three steps to answer the question of “How do you really sell bottoms-up?” for software companies.

1. Determine if the user get personal value.

Identify who has the pain point you are solving for — the individual, the team, or the organization. Align to that pain in the way you message.

2. Make sure your actual user can sign up for your product.

Provide value immediately by offering your solution for free. If it really solves a problem, hitting the paywall later will not turn them away.

3. Hire sales last.

Shift your thinking from needs-driven hiring instead of goals-driven hiring. Hire support first (to help your users), hire success next (to help teams using your product), and hire sales last (to finalize departments’ purchase of your solution).

Overall, you should be aligning your distribution persona to your product persona and follow the mantra “product leads, sales follows”.

Fireside Chat — Erik Troan, CTO and Founder of

Eric Tobias also sat down for a Fireside Chat with Erik Troan, the CTO and co-founder of Pendo, a product experience software for digital products and data-driven product teams. Erik began his career as the first engineer at Red Hat and has had a variety of leadership roles and learnings from success and failures over the years. Erik is extremely passionate about mentorship and culture in his organization and is one of the smartest technologists in the industry. Erik has a very strong point of view on how to lead and grow, especially on a technical team. A few highlights from his chat include:

  • Never hire a developer you wouldn’t put on the phone with a customer.
  • You learn a lot more from failure than you do from success.
  • Product people trust their gut too much.
  • Erik’s engineering managers really only deal with the technical part of management. They don’t deal with salary negotiations, 1:1s, and housekeeping. They have another management discipline which deals with personnel management, alongside the engineering managers.
  • As you grow, the company will inevitably change. You have to be able to anticipate those changes and adjust accordingly during team growth.
  • Make your customers your evangelists. Make sure they know you will do anything to make them successful.

Panel Discussion — Product Leadership

In the middle of the day, High Alpha Partner Kristian Andersen led a panel discussion with three seasoned product leaders:

The panel brought a healthy mix of discussion and dissenting opinions, all circulating around how product managers should be working with various functions in the organization. A concept that was first brought up was the controversial idea of a product manager being considered the “CEO of the product”.

  • “Conceptually this is okay, you want them to care about their project, but the real CEO should empower them. Organizational lines don’t have to be the only factor where accountability and decision making lies.” — Tim
  • “As a product manager, typically nobody reports up to you, so you need to inspire others to build your vision — see the big picture and translate that, which is often what a CEO does.” — Abbe
  • “You need to be the best advisor for the CEO of your product area.” — Doug

The panelists also shared thoughts on the alignment between product and marketing teams:

  • “Marketing should be tied close to the execution and invited to product meetings as early as possible to ensure alignment.” — Doug
  • “We should try and pull product marketing in sooner instead of just a handoff, bring them in early to bring the perspective of value to customers.” — Abbe
  • “There are lots of ways this can work—it depends on what you want to optimize for.” — Tim

When asked about where design leadership should live inside of the product organization:

  • “Centralization is important especially as the scope of your offerings grow, the best product decisions get made when you have a good balance between design representing the user, engineering representing the tech capability, and product representing the market.” — Tim
  • “You’ll be smarter with more people in the room earlier.” — Doug
  • Kristian closed the discussion referencing the three lenses of innovation often used by design studio IDEO:

Fireside Chat — Steve Sloan, CPO at Twilio SendGrid

To wrap up the day, High Alpha Managing Partner Scott Dorsey sat down for an energetic Fireside Chat with Steve Sloan, Chief Product and Marketing Officer at Twilio SendGrid. Steve’s unique position and background was a highlight that brought a lot of interesting takeaways to the table, especially around leadership.

  • When you don’t let folks at all levels talk and when the leader talks first, the voice of the customer is shut down. Let the folks who know your customer best have a voice. You need data and VOC to come through all the time.
  • You need to be aligned internally on what success means.
  • Customers who are angry are passionate and will generally pay to fix that issue. Customers who are apathetic generally don’t care as much and wouldn’t pay to solve that problem.
  • Killing products and work will always feel personal. The best way to do it is to get the data to prove that the work is not adding value to your customers.
  • Culture is key. Hiring for culture is good, but firing for culture cements to the organization that you’re serious about your culture code.

Flight Schools are an exclusive opportunity for our portfolio companies to come together to share learning and collaboration between companies, fully leveraging the benefits of the High Alpha network. If you’d like to attend a High Alpha Flight School in the future, check out our current job opportunities at High Alpha and our portfolio companies.