Remote work brings many efficiencies, from eliminating commutes for employees to reducing real estate costs for organizations. However, having a remote workforce makes the times that the team gathers in person all the more important. Team offsites – dedicated, extended period of times where a team gathers outside of the office – may be the only time that remote employees engage in real life, and are prime opportunities for planning, reflecting, and bonding. Offsites are a big investment in both time and money… every team member is not only potentially traveling on planes, but also taking a break from their day-to-day tasks to participate in the offsite. Considering these costs, it’s important the team leaders put significant thought and planning into an offsite in order to get the most value out of it.
Given this is such an important topic, I enlisted the help of my friend Kirsten Newbold-Knipp, a GTM exec who has led sales and marketing teams of 5-50 people at companies like FullStory, HubSpot and Bigcommerce. Our thinking is aligned on the value of offsites and I’ve included some of her best practices in this discussion.
The last several leadership teams I have been a part of operated remotely, and we developed best practices to make our offsites effective. This article is a tactical playbook to help you run a great team offsite. While the examples are often referencing startups and scaleups, many of the insights are applicable for division offsites at larger organizations as well.
With the decade long bull market and excessive fundraising environment, unprofitable startups are gobbling cash at a remarkable pace. The mantra is “grow as fast as possible, raise the valuation, figure out profitability later.” That can certainly work for some, unless the music stops. If there are unforeseen circumstances — a new product doesn’t work or the business model shows some flaws — that spigot of never ending money may stop flowing.
I felt this pain acutely at my last startup. We grew quickly and let hefty expenses, many for products and services that we didn’t even need, pile up. Our leadership team was eager to add more staff to scale, but we didn’t carefully consider how the additional costs would reduce our runway and increase our risk, especially if revenue did not grow as quickly as we projected, or if we couldn’t collect accounts receivables promptly. Not surprisingly, we encountered both of those obstacles. This forced us to make layoffs, which is agonizing for everyone involved. It was a valuable lesson learned and shaped my current philosophy on cost management.
When a startup begins acquiring customers, it feels pretty magical. Once the sale is closed, there might be a few manual processes in place, like writing down some detailed information about the customer, setting up the product for them and configuring automatic billing. What happens when we have 100 customers? Suddenly, we have a massive influx of new data to track. Is each customer getting billed properly? Do we know who the customer’s key contacts are so we don’t accidentally send them future marketing emails?
These challenges are precisely why a growing startup requires some basic business infrastructure: systems, processes and tools that enable us to do the important stuff (sales, marketing, product, etc) seamlessly. Most companies refer to this team as Business Systems or Business Operations. There are 3 simple goals for that team: