How I Survived Insane Hypergrowth at Airbnb

by Jonathan GoldenJun 07, 2019

As I reflect on my time as Director of Product at Airbnb, I already feel a sense of nostalgia. I get another emotion, though, when I remember the harder times. Helping the business scale like crazy was a roller coaster, and there were many moments when I was ready to throw my hands up and jump on a plane to somewhere across the world (to quietly relax in an Airbnb, of course).

Building a startup that is in hypergrowth is like few other professional experiences. The work environment is different every few months in every way, including the team members around you. The pressure of operating at a breakneck pace can seem insurmountable. But I was able to handle stressful situations much better as I matured as a manager and, more importantly, as an individual. Over time, and with a lot of trial and error, I developed a few rules that helped me build resilience and succeed in a hypergrowth environment.

1. Don’t just identify a problem. Start fixing it by enlisting others.

I cannot stress this enough: bring a solution to the table any time you spot a problem. For hypergrowth companies, there are problems everywhere, literally every place you look. Just saying that there is a fire somewhere, without helping to put it out, is not helpful.

Others may not know how big the fire is, so you first need to develop a case for sizing the problem. Typically, it’s a lot easier to get the green light to fix a problem than it is to get the resources. So be prepared. Think through what you need, and the timeline for fixing the problem, so you can present a compelling case for what it’s going to take.

I learned this lesson well during a particularly challenging moment at Airbnb, when I was relying on the mobile team to support long-term reservations. Though it was a large part of our web app business, that feature had never been built for mobile. For over a year, I asked the mobile team to take this on, pinging them monthly when my recurring calendar notification reminded me to. But while I’d identified a problem, I took no real action to aid in the solution. I was stuck in the seemingly logical conclusion that it was the other team’s responsibility. If I would just elevate the issue, they’d fix it.

Inaction made me increasingly frustrated. I contemplated complaining to the founders, an extremely immature move I’m glad I didn’t pursue. Instead, during downtime before the holidays, I built a plan: Taking the time to get the mobile engineers on board, I borrowed a few backend engineering friends on my team to work on the solution during the holiday break. It was outside the normal workflow of everyone involved. But by explaining the obvious and immediate impact to the business, and working directly and candidly with others, I built trust; in return, they gave me their time. We pushed the feature out in the first mobile release of the new year.

At the leadership meeting the following week, everyone around the table asked why mobile bookings had rapidly accelerated. I succinctly told the story of the team’s quick execution and the subsequent impact. Everyone was shocked that we hadn’t fixed this problem before — but extraordinarily happy that we’d finally closed a gap.

I’ve seen too many individuals (myself included!) identify problems but not be willing to help solve them. The hard work is in enlisting others to help fix what’s broken — educating colleagues, in a non-confrontational way, about the scale and scope of the solution and the resources required.

A team player who is constructive when problems arise is far likelier to advance, and advance quickly. Focus on outcomes, and you’ll become the coworker everyone wants to work with: someone who can inspire the organization to take action when they want to. Simply put, someone who can get it done.

2. Understand the (ever-broadening) context.

Being an effective team player isn’t just about solving problems as they arise. It’s also a matter of understanding, and contributing to, the priorities of the overall business. Because what matters to you most might not be what the company needs to focus on at a given moment in time.

I’ve witnessed coworkers become irritated when their work product is not presented in company meetings. They then either want to work on the latest shiny object or become withdrawn, assuming that their work is not important.

I get it. I’ve been there. In 2016, I couldn’t understand why Airbnb wasn’t spending more resources targeting business travel, which is roughly a third of the global travel market. Then in a one-on-one, Brian Chesky, founder and CEO, confirmed that it was extraordinarily important but that two other initiatives, while smaller in size, were more urgent at that moment due to competitive threats. Understanding that context completely shifted my perspective, and restored my motivation. What had been frustrating for months became an opportunity to align my work with leadership’s priorities. Brian and I plotted out a timeline for when the appropriate resources would be allocated to the business travel effort. Ultimately, it was only delayed by a year.

Since then, I have constantly strived to stack rank priorities and to reshuffle them as I gain awareness of the context in which I work. To thrive in a hypergrowth environment, you need to push your ego to the background. Focus on what is most essential to the company’s success instead of simply advocating for whatever’s in front of you.

Some startups claim that everything is a priority, but this can’t be the case. It’s up to the founders and leaders to be transparent about what is important for the year or the quarter so that the team can organize around these objectives.

Then, it’s up to you to figure out how you can support those objectives and scale in knowledge. As a builder, think about how your activities fit into the organization’s activities and how you can be even more impactful. If you are a manager, it’s up to you to weave the broader context into your team’s day-to-day work and message it compellingly. If you are successful in identifying problems and building consensus around solutions, the key is to always tie those efforts back to the company’s priorities.

3. Confront challenges head-on. You’ll get through it!

When a team encounters a challenge that they have never seen before, it can feel insurmountable. But look around you: those who have been through a few tough challenges before will seem to have a steadier hand. That’s only because they have dealt with hard times before, and seen them through.

It’s important to keep a positive attitude even when the heat is on. There will always be people who are ready to throw up their hands and claim that nothing will work. But here’s the reality: something has gotta work, or you’re a dead duck anyway. Don’t despair — make a plan and get everyone paddling in the same direction. Putting out fires is how you will spend most of your time, so think creatively. Take some risks. Just work through the issue and you’ll get to the finish line.

At Airbnb, we never needed positive thinking more than during the trust crisis of 2011, when a host’s home was trashed (and a front-page story ensued). The team is what got us through those difficult days and weeks. Even the founders slept with us on air mattresses in the office to respond to the crisis and make the product better than ever. I distinctly recall a financial consultant, though, who pulled me aside during all of this and pleaded with me not to launch Host Guarantee. She told me it would bankrupt the business. I heard her out, but I also recognized hers as a reaction of fear. She was playing it safe, focusing on avoiding the worst-case scenario, rather than actively pursuing a solution. It’s in these moments, though, that you actually need to double down on proactive, positive thinking.

Leadership is paramount, too. Because before action comes the mindset that you will get to the finish line — and that requires someone who can bring a team together to face the challenge at hand. As a startup scales, it will only face bigger problems and more complex decisions. But as you gain experience working through issues, those challenges won’t seem so formidable.

4. Everything changes all the time. Get over it.

It took me a while to realize that sometimes, in hypergrowth mode, everything just changes overnight. There are times when this may be unjustified — the whims of an exec, for example — and times when it’s extraordinarily justified, like when a major crisis appears and you have to respond.

When something changes, it doesn’t mean that everything the team was doing before was wrong. It just means that new information came into focus and prompted a refinement. Whatever your role, flexibility is crucial to surviving startup life.

For me, these rapid changes were initially hard to take. I’m a planner who likes to think through issues, lay out my methodology, and then execute. In 2012, I managed a team called User Tools, which essentially covered the entire product except for the booking flow. Everything a user did before a booking and after a booking was my responsibility. I didn’t love that structure, but I was happy to take it on.

When I was asked to build an annual product roadmap for the team, I took two months, collaborating with leadership and engineers to figure out what we should focus on. I laid out a compelling case — so compelling, I convinced everyone that the team really shouldn’t exist. There were too many objectives for one team to manage. We realized that the team should be broken up.

That presented me with an existential crisis. I was suddenly team-less. Was this the result of bad performance? I had to take it in and accept that, though I was affected, it wasn’t about me at all. I had actually been the leading contributor in the reorganization. Could we have realized this earlier and planned better? Sure. But it was also my work that led us down this path — ultimately a better path. I rallied our engineers and charted a new course, building a Payments team that took on an increasingly prominent role in defining and achieving the company’s product objectives.

It took many of these experiences to build up the fortitude to embrace high-velocity changes. Recognizing that these things are going to happen, and that my response mattered more than the changes themselves, would have served me well earlier on in my time at Airbnb.

If you’re in a leadership role, you have the added responsibility of rallying your team behind a new direction. Don’t say “nothing changed.” Acknowledge the change and explain the reason for it. Again, I can’t stress enough how important it is to be candid about the why. Organizations normally change for the better as they constantly work to make the team operate as effectively as possible.

Take solace in the fact that no organization is perfect. To survive, every company must change and flex. For instance, at Airbnb we reoriented the product team at least every year as the product’s external environment and community of users shifted. Change also doesn’t mean that something was wrong before. The internal organization simply needs to respond to exogenous factors.

The key is to look forward instead of reflecting on the sunk cost of your work. If the opportunity ahead is brighter than what you were pursuing before you changed paths, then it is the right decision. Don’t dwell on what you’re throwing out the window. Be open to the growth that this type of change typically brings.

5. It’s all about the EQ.

The most stressful situations were often the ones where my technical skills were least useful. During one particularly challenging period, I found myself continually butting heads with a colleague. He was an extremely logical thinker, and I fancied myself one as well. But we always ended up on opposite sides of the table, in every meeting. I would find one place to critique his thinking and he would do the same to me. It was so surprising, because deep down I thought we were actually on the same page. After a year of this — not kidding — I finally told him how I felt.

At Stanford, a class nicknamed Touchy-Feely (actually titled “Interpersonal Dynamics”) is known as the class where you get in touch with your emotions. I couldn’t find a way to relate on a rational plane with this colleague, so I decided to call upon everything I remembered from that class and take it to the emotional plane. I framed things in terms of how they affected me emotionally, not who was right or wrong in any given moment. Our conversation lasted for an hour and a half. When we parted, I didn’t know if he’d ever talk to me again. To his credit, he took it all in, but it took time. After a few months, we rebuilt a bridge of trust and are good friends today. That is the power of acknowledging that we are all emotional beings — even in the workplace — and learning how to manage those emotions.

My colleague and I went on to tackle many challenges together, including risky new product launches and organizational changes. Looking back, it was the greatest personal accomplishment I had at Airbnb. We both took risks and ultimately transformed a relationship. I am so thankful for it.

In Summary

Being good at your functional job is table-stakes in a dynamic, hypergrowth environment. With startups, you are commonly operating at the fringes of new technologies and behavioral changes; much of your work will be novel and have unknown outcomes. Being patient with others, understanding your own emotions, and identifying what your colleagues might be going through is the key to surviving hypergrowth. My greatest lessons from Airbnb came through how I responded to others, and how I channeled my own emotions into constructive action. Each stage of the company required an up-leveling of my emotional, communication, and leadership abilities — and those are the tools that I will carry forward.