Table of contents
Aaron Pacheco, CEO and Founder of OtterMon AI, once watched a project fail spectacularly, and it could have cost him his career. What saved it wasn’t a new plan or a bigger title. It was listening.
“If you go into a new role, the listening tour can make or break you.”
Aaron learned that a title gets you in the door but doesn’t get anything done. So before he fixes anything, he asks engineers, customers, and stakeholders what isn’t working and why. That’s where the trust and the real answers come from. He leaned on the same approach at New Relic, where he arrived without the relationships he’d built over years elsewhere.
Aaron started as a customer support intern at Acquia and spent nearly a decade rising to Product Lead on its Drupal cloud platform. One lesson from support stayed with him: make the problem the enemy, not the customer. As he moved up, the job kept changing. He stopped fixing the ticket in front of him and started asking what caused the last fifteen. He stopped leading on authority and started leading on data and relationships, because data stuck in a silo is useless.
“Every rung up the ladder, I had to think broader. I had to think more about money.”
He also walks Matt Peters through the leap to founding his own company. For 15 years, one problem kept him up at night: how many outages were preventable, and how the data to prevent them was always there but never put together. Leaving the safety net of a big company was terrifying, but one question made the decision feel obvious.
“There’s pain that is not being solved and somebody has to solve it. Why not me?”
Aaron closes with how The Lean Startup and its Lean Canvas exercise shaped OtterMon, and how he thinks about chat versus visual interfaces in the AI era.
What you’ll learn in this episode
- Why the listening tour can make or break a new role
- What to ask engineers, customers, and stakeholders before you fix anything
- Why a title alone doesn’t get things done
- Why you should make the problem the enemy, not the customer
- How the job changes at every rung, from fixing tickets to finding root causes
- Why data in a silo is useless
- How to decide when it’s time to bet on yourself and found a company
- How The Lean Startup can help you test a business idea
About Aaron Pacheco
Aaron “Checo” Pacheco is the CEO and Founder of OtterMon AI, an observability automation startup he founded in 2025. OtterMon unifies a team’s existing monitoring tools to help them move from reacting to incidents to preventing them.
Before OtterMon, Aaron spent fifteen years as an observability customer and product leader. He was Director of Product Management at New Relic, Co-Founder and Chief Product Officer at MyDecisive.ai, and spent nearly a decade at Acquia, where he rose from a customer support intern to Product Lead on its $140M Drupal cloud platform. He is based in Greater Boston and is also an award-winning fantasy author.
Resources mentioned
About the host
Matt Peters is the CEO and Co-Founder of Fixify, where he’s redefining the IT help desk for the AI era. Before founding Fixify, he was Chief Product Officer at Expel and held senior leadership roles at FireEye and Mandiant, where he helped pioneer some of the earliest managed detection and response services.
