Today we talk to Holly Hester-Reilly. Holly is a product expert with multiple leadership roles in hyper growth companies like Shutterstock and MediaMath. Currently, she works at H2R Product Science and advises multiple startups.

As founders, we must understand the people more than the system because this creates more value.

Holly’s love of software and technology paved her way into the startup world. Her experience as a product leader in various hyper growth companies enabled her to understand the business on a product perspective.

She is here to share her startup journey and the challenges she faced as a product leader at Shutterstock and MediaMath. We talk about how to lead teams and expand the support of the customer’s workflow. Also, Holly mentions about people dynamics and incentive alignment, what are good and bad OKRs, how to implement them in the team, and what leaders should focus on to leverage the company’s success.

Episode Quotes
"One of the best ways to build/launch software on a timeframe that works is to make sure that you are a person that it is safe to tell the truth to"
"It is a holistic thing; it is not just the analytic experiments but also knowing the market and the customers' needs, then sharing it to the team"
"Sometimes leaders do things that are mainly focused on accumulating power at the expense of the organization's growth"
"Good OKRs are those that clearly define the vision for what kind of value your team is providing"
"Money is a means to an end not the end in itself"
"If you actually empathize with people then you can make things happen and there is a lot of value"
"As a founder, make your people do their best work towards the company's vision above just achieving the vision"

Listen to Learn
00:32 Getting to know Holly Hester-Reilly - tech startup journey
03:30 Holly's core company building skill
05:50 Make-it-or-break-it moments as a product leader, How her core skill was helpful in
solving these challenges
11:19 Why is describing a product or product market a recurring problem for most founders?
14:17 How to leverage success and be antifragile? Learnings from the Shutterstock experience
17:47 People dynamics and the role of incentive alignment, Importance of implementing well
defined OKRs
21:52 Examples of good and bad OKRs
26:39 Trello's unique way of doing "wear your customer's shoes"
28:35 Non-Rapid Fire Questions
33:23 End notes and website links