What if performance reviews weren’t dreaded rituals, but living systems that actually made people better?
For Stefano Grossi, that question has guided both his leadership philosophy and his latest venture. With over 20 years in technology and product leadership, spanning firefighting, software engineering, and executive roles, Stefano has seen firsthand how culture, technical debt, and people systems can either accelerate SaaS growth or hold it back.
In this episode of SaaS That App: Building B2B Web Applications, Stefano joins host Aaron Marchbanks to share lessons from scaling FreshBooks, migrating 30,000+ customers off a legacy platform, and why he founded Branco.ai to reimagine employee growth with AI-driven continuous feedback.
From Firefighter to SaaS Technologist
Stefano’s career didn’t begin in tech boardrooms. Before building products and leading teams, he served as a firefighter and EMT in Italy. Those years taught him two lessons he carries into every leadership role today:
- Stress management under pressure. Emergencies don’t wait for calm environments. Learning to act decisively in high-stakes situations translated directly into managing complex technical projects.
- Camaraderie and trust. As he explains, “When you put your life in the hands of your team, that bond is unshakable.” For Stefano, building high-performance engineering teams is about replicating that same level of trust in professional settings.
By day, he was coding; by night, he was on call as a firefighter. That balance between discipline, risk, and learning new skills became the foundation for his later work in scaling SaaS.
Why FreshBooks: Learning Culture at Scale
When Stefano joined FreshBooks more than seven years ago, it wasn’t just about product. It was about culture. He wanted to understand how a company could scale globally while staying true to its values.
FreshBooks was already recognized as one of Canada’s best employers, and Stefano wanted to learn what it took to preserve and evolve that culture while growing teams across multiple geographies.
During his tenure, he moved from VP of Engineering to Chief Technology & Product Officer, launched FreshBooks’ European operations in Amsterdam, and oversaw key expansions in payments and payroll.
The biggest lesson? Culture evolves, but values endure.
“Values are the cornerstones of culture. Take time to define them and make sure that those are non-negotiables.”
From remote work to diversity and inclusion, FreshBooks’ culture shifted over the years. But the clearly defined values anchored the company through those changes.
Migrating 30,000+ Customers Off a Legacy Platform
One of Stefano’s toughest challenges came in the form of a large-scale product migration. The old “Classic” FreshBooks platform still hosted 30% of users but represented 80% of revenue.
Migrating that customer base wasn’t optional. It was essential to eliminate the “classic tax,” the drag on innovation caused by maintaining two systems.
The migration process included:
- Cross-functional decision rooms - ensuring sales, support, engineering, and marketing all had input.
- Decision logs - transparent documentation of every major choice, accessible to the entire organization.
- Biweekly company-wide updates - the same report that went to the board was shared internally, aligning everyone on progress, pain points, and metrics.
The result wasn’t painless, but it was transformational. Customers gained faster, simpler workflows, and the organization eliminated a 20–30% velocity tax on innovation.
Technical Debt and the Pyramid of Needs
Stefano is candid about technical debt: it’s unavoidable, but it must be communicated in a language executives understand.
“The only way you get your technical debt to be understood is if you translate it into dollars. That’s the way you need to explain it.”
To help teams navigate the balance, Stefano created the Pyramid of Needs:
- Keep the Lights On (KTLO): Uptime, maintenance, and reliability.
- Quality: Foundational stability before features.
- Enablement: Empowering other teams to move without blockers.
- Enhancements: Improving today’s MVP so it doesn’t stagnate.
- New Features: The tip of the pyramid, where most want to spend time, but only after lower layers are funded.
By framing trade-offs in this way, leaders can see that ignoring technical debt isn’t a savings; it’s a cost that shows up as slower delivery, churned users, and higher support volume.
Fail Fast vs. Outcome Over Output
The startup world often idolizes “fail fast.” Stefano agrees, but only in the right context.
You don’t want to fail fast with uptime or customer trust. But when experimenting with new features or go-to-market strategies, speed of learning is critical.
For Stefano, the real shift is focusing on outcome over output:
- Output = shipping a feature.
- Outcome = achieving the desired business result.
He pushes teams to define which number they want to move adoption, retention, engagement and then run experiments toward that goal. Learning, even without success, is still a valuable outcome.
Why Stefano Founded Branco.ai
After two decades of working with performance reviews, Stefano grew frustrated with how broken they had become. Reviews were backward-looking, checkbox-driven, and often demotivating.
Branco.ai was built to fix that. The platform integrates directly with Slack to deliver continuous, peer-driven feedback. Every week, employees receive short prompts to share feedback with their peers. Over time, that feedback compounds into 200+ actionable data points per year, far more than any annual review could provide.
Unlike generic AI “coaching tips,” Branco’s system:
- Anchors feedback in company values and leadership competencies.
- Translates vague advice into specific action steps (e.g., “In your next team meeting, share your decision process and ask for feedback”).
- Builds an evolving action plan personalized for each employee.
The goal isn’t just efficiency. It’s making leadership development and personal growth part of the daily workflow.
What’s Next for Branco.ai
The company is in its soft-launch phase, already showing promise with early clients. Success metrics include predicting employee attrition, driving promotions, and saving managers hundreds of hours in review prep.
The next focus is equipping managers with better reporting and coaching tools, turning continuous feedback into systemic growth for entire teams.
For Stefano, the vision is clear: end broken performance reviews and replace them with living systems that truly help people and organizations thrive.
Stefano Grossi’s journey, from firefighting in Italy to scaling FreshBooks and launching Branco.ai, highlights the intersections of leadership, culture, and innovation in SaaS.
His lessons are a reminder that:
- Values outlast culture.
- Technical debt must be translated into dollars.
- Outcomes, not outputs, drive real innovation.
- Continuous feedback is the future of performance management.
For SaaS leaders, the takeaway is simple: scaling isn’t just about shipping code or chasing growth. It’s about building teams and systems that last.
Stefano Grossi Background
Stefano Grossi is an executive technologist, product leader, and founder of Branco.ai, a B2B platform that uses AI-driven feedback and action plans to align company strategy with employee growth. He is also the Chief Technology & Product Officer at FreshBooks, where he has led product innovation, international expansion, and integrations such as Stripe Connect and payroll. Previously at SOTI, he scaled product teams by 500%, introduced Continuous Delivery and Infrastructure as Code, and increased profitability by 40%. With a background that spans firefighting, engineering, and executive leadership, Stefano is known for building high-performance teams and pioneering new approaches to culture and performance management.
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