Inside Breather: Working in product at a rapidly scaling startup

Christine Montgomery was employee 100 at Breather, a Montreal-based startup that rents on-demand, Architectural Digest-esque workspaces by the hour. In the year since Christine joined the company, Breather’s headcount has doubled. And their product has expanded to new markets across North America and around the world.

That’s a lot of growth. And with that much growth comes huge opportunity—but also way more complexity. After years working in product at a legacy media company, where processes were deeply entrenched, Christine traded tried-and-true for chaotic-but-way-more-creative. She shares some observations from her first year as a product manager at a rapidly scaling startup.

Why did you want to join Breather?

It was one of those things where I went to the website and immediately understood what they were trying to do. It clicked right away. But I was particularly attracted to working with a physical product and working in the realm of service design where software actually meets the way people interact with space. And I was really attracted to the idea of working with an interior design team. Immediately when I saw Breather, it clicked.

Coming from a corporate background, were there any “habits” you had to break?

At my last company, despite it being large, the digital team very much worked in an agile environment. We were almost in a silo for a good portion of when I was there. We were heavily, heavily processed, but that process worked very effectively. And when I came to Breather, we did not have any process at all. I was used to having a partner and a scrum master. I had to readjust and embrace the chaos of a startup. And figure out how to deliver value in that environment.

And the other thing, which was so extremely positive, was I think when you work in large companies, there’s almost a manipulation of the facts. At Breather, there are so many really strong people who work here who want a really honest understanding of how effective our product is. I like the upfrontness of a startup. That was super refreshing.

What are biggest product lessons you’ve learned since you started at Breather?

So the first one, as I was touching on before, is to embrace chaos, be comfortable with vagueness, and focus on value. If I had to pick one thing, it’s absolutely that. It’s really challenging. But you always have to be thinking: what’s the most valuable? It’s okay that we don’t have a process for this. It’s okay that we’re still figuring it out, because we know what the mission is, and we’re going to find what’s valuable.

"I have no idea what this is. And I have to lead this team. And everyone knows more than me."

Another thing is: treat everything you build like it could be thrown out. In product management now everyone has really embraced this MVP and fast delivery culture, which is amazing. And you really need to be able to live and breathe that, because we’re still discovering what our product is. So everything we do must be fast and unprecious.

What are some of the ways you focus on value amid chaos?

I try not to worry too much about frameworks. I do think they’re important, and becoming increasingly important as we grow. But one of the mistakes we made as a product org in the past year is to be very focused on process, versus people-focused.

It can definitely be challenging to focus on value when you’re a scaling startup. In my last position, it was very easy to be data-driven because it was a legacy product where we knew everything about it, we had a very established API. We had all of our tools in place to measure. Whereas at a startup, we’re still building those things. You really have to focus on how well an initiative aligns with the mission of the company and the key strategies.

Are there business advantages that come out of chaos?

The advantage of chaos in a scaling business is speed and independence. There are times when it’s been unclear what’s going on, or who owns what, but the benefit is that innovation can come out of that. It gives people autonomy to try new things.

What are the hardest parts of being on a product team at a company that’s growing so quickly?

One major challenge for us is that Breather became international very quickly. We have spaces in Canada, in the UK, all over the US, and we’re expanding elsewhere very soon. So ensuring there’s strong communication and a strong feedback loop when you get international so quickly is definitely a challenge. We have people all around the world who really understand the business and especially understand it on the ground in their city. And keeping those communication lines open has been a challenge that we’ve had to overcome.

I think you go through a bit of a pendulum when you’re scaling. We have gone from being very, very centralized and very slow as a product team, but very thorough, to being very chaotic. We did this whole cross-functional transformation that made us very, very tied with the engineering team. We were going a lot quicker, but then we suffered on the communication side.

So now we’ve swung the pendulum another way towards being an engineering-focused product team. I think a big challenge has been that pendulum back-and-forth. We’ll probably continue to swing, but that’s what the job is.

Can you map out more specifically how your product org has evolved since you started at Breather?

When I started, we had an independent product team, and we very much worked in a waterfall. We had a pretty dry backlog, and it was very heavy in terms of actually getting to the point where we would work with the delivery team. We recognized this as a problem, and said, “What can we do about it?”

"You can’t solve communication, but oftentimes the answers to improving it are quite simple."

So we went cross-functional. And we just went headfirst into it. And then we had product managers very integrated into delivery teams, but we did not maintain the centralized function of a product org at that time. At this point we did not have dry backlogs anymore, but coordination suffered and vision suffered, and being able to connect the work to the mission was also something that we had to work through. So Breather right now is moving into this dual-track product discovery methodology where we maintain a centralized product org, who collectively think about the delivery of our product and the whole customer journey.

How do you stay close to the customer when also dealing with the pressures (and chaos) of rapid growth?

We have a user research team here. We have an insights team that leads the charge on ensuring that we know our personas and that we’re doing analysis on qualitative and quantitative data. But we’re still figuring out how to account for local nuances. I see that as a challenge that we’ll always have.

When you go into new countries, there are certain things that we didn’t think about in terms of product. We’re used to certain kinds of search methods, whereas in a different country they’re actually used to a very different pattern. Payment methods differ from country-to-country. So it’s great to have global teams embedded and to be listening to them, because they provide a great feedback loop for us in terms of: what are the major considerations we need to bring to the product to be able to understand localization?

What are some of the strategies you put in place to improve communication?

One thing we’re working on right now, it sounds really simple, but it’s release checklists and communication checklists. I was reading a book recently—this was kind of how this came about—called The Checklist Manifesto. It’s written by a surgeon who talks about implementing checklists in surgery. Surgeons, because they have such a complicated job and they have so much to consider, often forget about the basics. They don’t remember the patient’s name. This happens when you work in complex environments. People always think that simple things are redundant. But I’m trying to find those simple wins.

I really believe communication will never be solved by anybody in a company. It will never be perfect. You have to repeat things a hundred times. You can’t solve communication, but oftentimes the answers to improving it are quite simple.

Are there any other processes you would like to put in place to help manage growth?

On the delivery side, I’m a huge fan of self-organizing, agnostic, cross-functional teams. I actually am not super keen with developers being associated to a function. I think they should first and foremost form small teams based on people they think they work well with. Then you have teams that are made up of people who like working with each other, and those are always the most successful teams.

What I’ve seen in the past is that you end up having certain teams that like the more business-as-usual, administrative stuff. And there are other teams who want to do the crazy, hacky stuff. And you let them float there. So I would love to see that happen.

"Everything we do must be fast and unprecious."

The other one, which I’m very keen on, is this idea of iterative research. We’ve gotten really, really good at rapid delivery. And understanding MVP and getting small chunks of software out that provide incremental value. We’re so good at that. But I think where the product community still has so much opportunity to grow is applying the same methodology to how we research and how we understand what our products are. So we get away from the point where we’ve done a 4-month project on building user segments and those are our segments for the next year. It’s like, “How do we break that up?” We can learn a lot from MVP, agile delivery methods and be a lot more iterative about research.

How would iterative research manifest in reality?

I think an example of that would be, let’s say you’re building your personas. You don’t need to wait until you know exactly who your personas are and you’ve synthesized the data and done all the quantitative and qualitative analysis to understand your persona. You can do an interview and ship it and that becomes part of it. And then you can do a survey, put it out there, and iterate again. You don’t have to wait until all the pieces are together.

From a personal perspective, what’s been your most stressful moment and your most gratifying moment from the past year?

In terms of personal chaos, I moved into an operations role in the company having no idea what I was doing. My boss was like, “I think this would be an amazing focus for you, I think it really complements your skill set. As product manager, communication and organization are some of your strong suits, so I think you’ll be really good at this.” And I was like, “What is he talking about? I have a demand background. I come from a content and marketing space, I have no idea what this is. And I have to lead this team. And everyone knows more than me.”

It ended up that my most stressful moment is my most gratifying, because I actually did end up loving it. And found out that it was something that worked really well for me. And it was gratifying in the sense that I got to learn about this entirely new side of the business that I had no familiarity with, but that I’m actually super interested in and very excited about.


Looking forward to the next year, how do you see your product team and yourself as a product manager evolving to meet the needs of growth?

I think as we grow what I’m really looking forward to is focus. You wear many, many hats as a product manager in a scaling startup, and you do a lot of different roles that are outside of what you would traditionally consider product management. And that’s awesome. It’s really cool to be able to do that, but I also look forward to focusing on long-term product initiatives. And just as I said you have to treat everything like you can throw it out in a minute, it’s going to be awesome as well to do some long-term thinking.

We have some room to think about these really cool, innovative, R&D-oriented product things. And because we work with physical space and software, there’s going to be a lot of really interesting things coming out of Breather in next year or two in terms of product that are very—for the lack of a better word—futuristic.

What fun. What more could a product-and-technology-oriented person want than to be working on the latest things and to be working on innovation?