Happy software starts with happy teams: Isaac Mann talks successful engineering leadership

HappyCo’s Director of Engineering never shies away from complex problems. In fact, Isaac Mann has longed to solve them ever since he was little. “As a kid, I was massively into Lego.” For Isaac, every Lego endeavor unfolded like this: “I always started with a goal in mind, thinking: ‘I wanna build this thing.’ Then, I got down to the base structure and made sure it was color-coordinated, that it captured my imagination — i.e. if this were the real world, how would it be built?”

Flash forward to 2019, and you’ll find Isaac posing just these questions (minus the color-coordination!) as he leads HappyCo’s engineering team. “We’re always going from the idea of first principles, where you frame the conversation around what you’re trying to achieve.” To Isaac, that means fostering a culture of collaboration — not commands. “We facilitate engineers asking the right questions, making sure that one person doesn’t do their task and simply hand things off to the next person. Instead, there’s a consultation built into every phase of the project.”

Isaac says encouraging this kind of healthy debate is critical: “when someone creates in isolation, the code can go in a downward spiral. That’s why we make sure there’s always someone you can turn to and ask if something is a good or bad idea.” As reasonable as this sounds, Isaac says it’s rarely the case at software companies. “Honestly, a lot of engineers have had thankless jobs… because people don’t train their managers well. So, as an engineer you’re asked to do six days of work by tomorrow. That means hacking the life out of it and creating technical debt that can’t be easily solved.”

At HappyCo, Isaac has worked tirelessly to scrap that old story and create a wholly different dynamic. “Here, Product and Engineering agree on an outcome and build a path together. As I see it, you’ve got a decision chain. The more support you give that chain, the better and faster the decisions you can make.” Interestingly, Isaac says his team’s “small but agile” nature is the key to HappyCo’s success.

"Here, Product and Engineering agree on an outcome and build a path together. As I see it, you’ve got a decision chain. The more support you give that chain, the better and faster the decisions you can make."

“If you’ve got a massive team, it’s very hard to change the culture — it’s like trying to change the direction of a ship using a paddle.” Whereas at HappyCo, when Isaac hires new engineers, “they hear the same message: that we build together, treat each other well, and care to develop our skill sets.” On the professional development front, Isaac also goes against the grain by refusing to separate his team into front-end and back-end specialists. Instead, he hires candidates with “one or two primary skill sets” and then sets up a framework to enhance their secondary skill sets. This strategy, Isaac explains, makes HappyCo truly “feature-oriented”; engineers develop the breadth of their abilities so they can meet customers’ evolving needs.

This strategy, Isaac explains, makes HappyCo truly “feature-oriented;” engineers have the training they need to meet customers’ evolving needs.

But there’s something else inherent in HappyCo’s business model that paves the way for delightful software. In a word? Focus. By tailoring its product around rental housing inspections and the data they capture, HappyCo has avoided a stumbling block so common in software: “creating a lot of sprawl.” As Isaac stresses, “companies with a wide focus change one thing and it can put so many other things out of sequence.” HappyCo, on the other hand, benefits from its specific lens within the multifamily sector. “We can improve our architecture and decrease technical debt at a high rate because of our clear focus.”

Pacing is at the heart of the equation, too: “when you try to crank out a product too fast, you end up with problems that are expensive to fix.” Isaac’s team, on the other hand, operates with this understanding in mind: “catching a bug in design, even before you code, is cheap. Relying on end-user testing is not the stage where you want to find trouble.” Indeed, sensing trouble is precisely what Isaac empowers his staff to do — every step of the way. “We have a crowded quality assurance environment on purpose, where everybody dips into someone else’s job a bit. It’s valuable because it keeps engineers close to the effect of their software on the users.”

In this respect, he ensures that his team lives up to Kaizen, a HappyCo core value centering on continuous learning, continuous improvement. From Isaac’s perspective, the benefits abound: “when engineers can contribute to the whole chain, you get better at making a quality product.” Plus, at a tight-knit company like HappyCo, the collaborative process unfolds with a genuine sense of camaraderie: “when you keep a small team, you maintain a personal connection with people.”

"When engineers can contribute to the whole chain, you get better at making a quality product."

For Isaac, creating a positive environment is key to engineering management: “we’re building a team that enjoys building software. We always try to make it rewarding, giving them that dopamine effect of creating and completing something as a team.” Working on any product within HappyCo’s suite, Isaac and his engineering staff truly follow in the footsteps of HappyCo’s CEO and CTO: “Jindou and Mackross have always believed in building software that’s delightful — and it’s really something we’ve internalized as a group.”

Above all, Isaac feels grateful that in creating delightful software, he makes customers happier, too. “The more you dig into software, the more you’re directly solving problems — getting at how people think of things, building a taxonomy and actually finding solutions for people.”