Engineering Evolution: A Retrospective on Growth

By our Director of Product Management, Ani Achugbue

Retrospectives are integral to agile software development, but they don’t have to stop there. On the verge of a growth moment, it’s helpful to apply the same strategic reflection to the development of your engineering operations.

As we gear up for the next stage in our journey to help Vacasa become the largest and most technologically sophisticated vacation rental management company in the world, I wanted to share a quick retrospective on the evolution of our approach to technology.

First, a little background.

I left Nike to introduce product teams at Vacasa because I wanted to help develop something new. It was exciting to forego the relative comfort of a smooth-running machine to chart a new course in uncertain territory.

At the time, Vacasa was still operating like a startup. Engineers were working more as emergency responders than creators. Each functioned as an individual unit—scrambling to reactively put out fires with no insight into what one another were doing. There were no economies of scale, no coordination, no long-term strategy. Requests came in; code went out.

The patchwork of solutions was a work of art, but it wasn’t built to last. So, we met to re-orient ourselves and identify the weaknesses in our own system. We concluded that in order to do our best work, we would have to transform the way we function and build an entirely new system. We committed to transform Vacasa’s relationship with technology from reactive to strategic.

Requests couldn’t keep going to engineers independently, so we created an intake funnel designed to work for everyone in the organization. Silo-ed teams resulted in overlap, so we prioritized visibility, which helped us increase efficiency and get more from our bandwidth. Not having a repeatable dev process slowed our ability to roll out new products, so we implemented Scrum and streamlined productivity dramatically.

To help make it all happen, we added a group of awesome product managers. By focusing efforts, streamlining processes, and managing back at the organization, they helped set us on the path to becoming a stronger, more successful technology operation. Together, we showed Vacasa just how impactful it can be when engineers have the ability to operate from a place of strategy instead of on their heels.

Like most companies, when it was smaller, Vacasa primarily valued speed and scrappiness from its engineers. But we’re a bigger, more complex organization now. And we’ve matured as a team. During my tenure, I’ve been honored to watch engineers and product managers here come together to successfully evolve our approach to technology beyond tactical reactivity into strategic programming.

As Vacasa prepares to take the next step and transition into an increasingly engineering-driven organization, it’s important for us to celebrate how far these teams have come and reflect on what we’ve learned along the way about setting up our engineers for success.

The short-term accommodation industry is growing faster than any of us ever imagined, opening up countless technological opportunities to re-define the vacation rental space. This year, we hired fintec alum Tim Goodwin as CTO and welcomed Nordstroms SVP Brian Gill—formerly CTO at Expedia and Hotwire—to our board. We anticipate doubling our engineering and product teams over the next year. We’ve come a long way in a short time and this is only the beginning.

Our product and engineering processes at Vacasa are still not as streamlined as what I experienced at Nike, but we continue to mature rapidly. If we’re able to maintain our ability to grow and adapt, the coming years will see this team create products unlike the industry has ever seen—and launch them at global scale.

I’m fortunate to work with a group of brilliant engineers and product managers who, like me, believe that building the future of an industry requires great minds, clever code, and a drive to constantly develop how we work together within a rapidly growing organization.

Want to help transform the vacation rental industry? Join our team.