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.
Key Takeaways
[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.
Tweetable Quotes
"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
SaaS Leadership Lessons
- Lead with Feedback Openness: Proactively create a culture where feedback is routine, safe, and celebrated—not something to fear.
- Prioritize Psychological Safety: The best innovation happens when team...
Popular Podcasts
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!
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.
Cardiac Cowboys
The heart was always off-limits to surgeons. Cutting into it spelled instant death for the patient. That is, until a ragtag group of doctors scattered across the Midwest and Texas decided to throw out the rule book. Working in makeshift laboratories and home garages, using medical devices made from scavenged machine parts and beer tubes, these men and women invented the field of open heart surgery. Odds are, someone you know is alive because of them. So why has history left them behind? Presented by Chris Pine, CARDIAC COWBOYS tells the gripping true story behind the birth of heart surgery, and the young, Greatest Generation doctors who made it happen. For years, they competed and feuded, racing to be the first, the best, and the most prolific. Some appeared on the cover of Time Magazine, operated on kings and advised presidents. Others ended up disgraced, penniless, and convicted of felonies. Together, they ignited a revolution in medicine, and changed the world.