The Future of Work: Embracing Offsites in Technology Startups

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In the wake of a global shift towards remote and hybrid work models, technology startups are increasingly turning to offsites as a means to foster connection, collaboration, and culture among their teams. Jared Kleinert, Founder and CEO of, shares his insights into this evolving trend, underscoring the pivotal role of offsites in shaping the future of work.

Connecting in a Disconnected World

“We spend 50% of our waking hours at work and increasingly we're all with remote or hybrid or distributed companies," Jared explains. This statement highlights the crux of the challenge faced by remote-first companies such as Automattic, Buffer, Zapier, GitLab, and 15five, who have long recognized the value of bringing teams together in person to enhance cross-department collaboration, employee engagement, and strategic planning.

The Genesis of

The pandemic catalyzed a dramatic shift in work models, prompting Jared to envision a future dominated by remote and hybrid organizations. This foresight led to the creation of, a platform designed to simplify the planning of team retreats.
"I was making a bet that every company was going to be remote or hybrid in the future...And I realized there wasn't much software to make offsite planning easier," Jared explains. Today, stands as a leading solution for companies seeking efficient, stress-free offsite planning.

Tailoring Offsites to Organizational Needs

The approach to organizing offsites varies widely across companies, reflecting differences in team size, company stage, and the degree of team decentralization.
Jared shares that itself hosts two company-wide offsites annually, supplemented by quarterly leadership meetings. This model adapts as companies scale, with larger organizations potentially organizing multiple large gatherings alongside department-level offsites to maintain intimacy and foster specialized collaboration. This model is quite common, with January and June being the most popular months.

As companies get larger (up to 500 or even 1000 employees), they often prioritize at least one all-hands meeting annually. Then the approach often shifts to two or three larger gatherings to maintain the intimacy, with more frequent department-level and specialized off-sites–for example, sales kickoffs, presidents clubs, gatherings around conferences, perhaps around conferences. Product and engineering teams might have quarterly offsites around how they build out their sprint cycles and around certain product pushes.

Insights on Offsite Planning

Delving into the logistics of offsite planning, Jared notes a preference for centralized locations that ease travel for globally dispersed teams. North America, particularly major cities and areas with proximity to international airports, emerges as a popular choice, alongside destinations like Cancun and Lisbon. Seasonality also plays a role, with companies opting for warmer locales during colder months or embracing nature retreats in the spring.

The Evolution of Offsite Experiences

The trend towards boutique and experiential locations marks a departure from traditional corporate retreat settings. This shift is driven by a desire to create memorable, unique experiences that foster deeper connections among team members. "Building deeper connections with your colleagues at work is really about creating unique shared experiences," Jared remarks, highlighting the strategic advantage of selecting compelling destinations to enhance employer branding and team cohesion. partners with companies like Getaway and Autocamp that have experiences in nature. They also work with various resorts. “It makes for a much more exciting experience versus being stuck in a conference room for three days,” Jared explains.

Financial Considerations and Length of Offsites

Inevitably, cost is a consideration for offsites, and there’s a range of what startups can afford. Jared suggests that the average cost tends to be around $1,800 to $3,300 per person (with an average around $2,200), inclusive of all expenses. The duration of offsites typically ranges from three nights to a full work week, tailored to the specific objectives and size of the attending team.

The Journey Ahead

Reflecting on the trajectory of and the broader offsite landscape, Jared acknowledges the uncertainties posed by global events and economic shifts. From COVID to a tech recession, companies have faced concerns about both safety and costs. While many companies are still hurting, “for the most part, we've seen companies slowly but surely be okay with making these investments and realizing that they don't have a better alternative.”
He’s optimistic about the enduring relevance of offsites, "You can't run a remote company and not meet for two, three years...if you're going to do it, you might as well invest meaningfully."

Key Takeaways for Successful Offsites

In an era defined by remote work, technology startups are recognizing the invaluable role of offsites in cultivating a connected, engaged, and vibrant organizational culture. The right approach to gathering in person (whether you want to call it an offsite, retreat or workcation) will be different for every company, but it’s clear that the future of work is not just about where we work, but how we come together to inspire, innovate, and thrive as a community.