Balancing the Grind with Geoff Roberts, Co-founder of Outseta

Geoff Roberts is the Co-founder of Outseta, an all-in-one platform offering fully integrated CRM, subscription billing, and customer messaging tools.

1) To kick things off, could you tell us a little about your career background and current role?

Sure! So I found my way into tech accidentally—I was a writing major in college and had aspirations of being a sports or travel writer. I graduated in 2008 as the economy was crashing—newspapers were folding and I didn’t want to be a professional blogger, so I went back to school and got a MBA. 

After grad school, the economy was still doing lousy and I needed a job—a start-up called Buildium in Boston offered me a job as their first full-time marketing hire. It was a small company of less than 10 employees, and frankly I had no real interest in software.

But I was walking into a great situation and team really without realizing it. I spent the next 5 years leading the marketing team at Buildium, helping the company scale from a start-up to over 10,000+ customers and $15M+ in revenue as we grew to 140+ employees. I fell in love with start-ups and all things growth related in the process. Buildium was acquired at the end of 2019 for $580M.

After I left Buildium I lead marketing teams at a couple of other venture backed SaaS start-ups, then I teamed back up with one of Buildium’s Co-founders, Dimitris Georgakopoulos, to launch my current start-up, Outseta. We’ve been focused on building the business for the last 3.5 years now. 

2) What does a day in the life look like for you? Can you take us through a recent workday?

My days are admittedly a bit hectic at the moment! I have 7-month old twin boys, I work from home, and my wife was laid off due to COVID. As you might expect, days are a bit hectic on the home front right now.

We get up around 6:00am and feed the kids, and I usually start working by 7:00am. I spend the first couple of hours of the workday responding to email and customer service requests from our users, then typically take a short break to go for a run or surf.

Late morning or early afternoon I try to make sure I have a few hours of heads down time where I can focus on deep work, then I usually end up providing some relief to my wife in the afternoon so she can take a breather from watching the kids. 

Generally speaking, I do a really good job with work/life balance—I always find time for fun, for exercise, and I cook dinner almost every night. But I don’t adhere to a strict schedule and work is typically interspersed from 7am-7pm with the breaks that I mentioned. This may not be perfectly ideal, but it’s what we’re making work at the moment under these bizarre circumstances. 

3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?

Yes, I’ve been working remotely since 2013. At this point, I wouldn’t have it any other way—I fully understand the benefits of a co-located team, but the advantages of remote far outweigh the disadvantages.

Remote more than anything provides a vastly improved quality of life for employees, and my primary motivation at Outseta is to build the most human friendly workplace on the planet. I really believe that the company should exist to serve the life of its employees, rather than employees existing to serve the business.

Our About Us page will give you a better sense of how we run the company, and the language below on how we behave is pulled straight from our operating agreement. 

How do we behave?

• We look to invest in, develop, and fill open roles with employees/members first.
• We optimize for the best people possible by embracing remote versus co-located work.
• We value flexibility, but we honor our commitments to each other.
• We think long term over short term and care more about the journey than the destination.
• We embrace self management, encouraging autonomy and empowering our people to make decisions openly and transparently without managerial oversight.
• We earn influence by consistently demonstrating great work and decision making.

4) What does work-life balance mean to you and how do you work to achieve that goal?

I think the notion of work-life balance implies that work and what you do outside of work are served up in equal portions, but to me it’s more about the freedom to allow work and life to ebb and flow.

As co-founder of an early stage start-up (and with COVID-19), I’m currently working as much as ever but I also have the freedom to take a break when I want to. In 2018 I traveled with my fiance for 6 months, working probably 20-30 hours a week, having the freedom to scale up or down based on your interests and what’s most important at the time is work-life balance to me.

For me this had never been particularly challenging—I’m hugely motivated at work, but I have a lot of interests outside of work that I’m passionate about and engaged with.

5) In the past 12 months, have you started/stopped any routines or habits to change your life?

Having twin boys changed everything for me—I’m now routinely up at 5:30am and rarely stay awake past 10:00pm. This change was forced on me—I’m not a morning person—but I have discovered that I’m particularly productive first thing in the morning while my mind is still fresh. I do most of my best work before noon, and try to schedule meetings for the afternoon.

6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?

I think everyone that’s found their way to your website should be required to read Reinventing Organizations by Frederic LaLoux and The Advantage by Patrick Leoncini. There books have had an outsized impact on how we’re building Outseta and are a great resource for anyone looking to build a high performing, highly humane organization.

7) Are there any products, gadgets or apps that you can’t live without?

No. I’m an analog guy in a digital world. I know that sounds strange coming from a Co-founder of a tech company, but I think many times technology actually makes us less productive than we might otherwise be.

People who are techy generally have no sense of this—half of the “productivity hacks” I hear getting thrown around in the tech world help you manage/use your other technology products more efficiently. For me, unplugging everything is usually far more effective.

8) If you could read an interview about work-life balance by anyone, who would that be?  

Barack Obama. The role of the President just amazes me—the stress, the hours, everything. Frankly I don’t know why anyone would want to do that to themselves, and it seems crazy to be that the politicians in this role are often in their 70’s. How can you possibly maintain that schedule and all of the demands of the role and still be effective? Let alone awake!

9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?

I wish people would talk less about productivity hacks and “the future of work” and instead focus on how we can build more inclusive and employee friendly workplaces. The emphasis for me isn’t enough on how we can simply treat people better—like people—like how we’d want to be treated ourselves.

I think the more you treat employees great and look to support them not just professionally, but in all aspects of their life, the more loyal and engaged they’ll become. I believe that this isn’t just the right thing to do, but it can also directly drive better business results. I think we’ll see that proven out even further over the next 50 years.

Before you go…

If you’d like to sponsor or advertise with Balance the Grind, let’s talk here.

Join our community and never miss a conversation about work, life & balance – subscribe to our newsletter.