In this insightful episode of SaaS Fuel, host Jeff Mains is joined by Mary Moore Simmons, VP of Engineering at Kibo. Together, they dive into the realities of building and scaling high-performing engineering teams, especially in fast-growth SaaS environments.
Mary unpacks the nuanced challenges of evolving organizational processes, cultivating feedback-rich and psychologically safe cultures, handling “brilliant jerks,” and integrating AI to reduce grunt work and boost developer creativity.
Tune in for a practical playbook on scaling teams, optimizing ways of working, and navigating technical debt as a business strategy, not just a developer’s gripe.
[00:00:00] Feedback-Fueled Leadership: Mary's greatest fear as a leader is not knowing where she or her team might be going wrong—emphasizing feedback as the antidote to blind spots and organizational toxicity.
[00:04:53] Process Check: When engineering processes feel slow or clunky as you scale, it's a sign to revisit and adapt. The right process should always speed teams up, not slow them down.
[00:06:52] Culture First Hiring: Early hiring mistakes often relate to compromising on culture or failing to address culture misfits as teams grow. Brilliant jerks cost teams more in the long run, even if they are individually productive.
[00:14:50] Handling Exits with Transparency: Delivering clear expectations and feedback means no one is surprised by tough decisions; transparent communication helps maintain trust when high-performers are let go for culture reasons.
[00:20:38] Normalizing Feedback: Build an environment where feedback is everyday and safe—not just a scary signal of things going wrong. Celebrate when people speak up early and often.
[00:27:00] AI Adoption: AI tools are powerful but still come with learning curves. Early adoption requires empathy and encouragement, especially in startups, and the biggest impact comes from knowledge sharing among engineers.
[00:44:44] Technical Debt as Strategy: Make the business case for addressing technical debt—frame it with impact, not just engineering complaints, to get real buy-in from business leadership.
"My greatest fear as a leader is that I’m messing everything up and no one’s telling me because they’re too afraid." — Mary Moore Simmons
"Process should always be speeding people up, not slowing them down." — Mary Moore Simmons
"Hiring a brilliant jerk might make you faster today, but it will drag your team tomorrow." — Mary Moore Simmons
"Feedback should be constant and small—don’t let it become a scary event." — Mary Moore Simmons
"Technical debt is not a developer gripe. It’s a strategic conversation with real business impact." — Jeff Mains
"AI tools double my speed, but they can also take me ten times in the wrong direction if I’m not paying attention."— Mary Moore Simmons
Viral Topic: Amplifying Teams with AI
"It's less about automation and more about amplification so if you're building a team, evolving your culture, or just trying to make scaling a little less chaotic, this episode has the clarity you didn't know you needed." — Jeff Mains
AI & Automated Testing: "without automated testing, everything breaks. And I've experienced that. I think probably a lot of other founders have experienced that." — Jeff Mains
New Heights with Jason & Travis Kelce
Football’s funniest family duo — Jason Kelce of the Philadelphia Eagles and Travis Kelce of the Kansas City Chiefs — team up to provide next-level access to life in the league as it unfolds. The two brothers and Super Bowl champions drop weekly insights about the weekly slate of games and share their INSIDE perspectives on trending NFL news and sports headlines. They also endlessly rag on each other as brothers do, chat the latest in pop culture and welcome some very popular and well-known friends to chat with them. Check out new episodes every Wednesday. Follow New Heights on the Wondery App, YouTube or wherever you get your podcasts. You can listen to new episodes early and ad-free, and get exclusive content on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. And join our new membership for a unique fan experience by going to the New Heights YouTube channel now!
Dateline NBC
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On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!