Company Culture, Expert Insights, Team Morale

Expert Insights: Jared Kleinert on Meaningful Company Events For Remote Workforces

Here at, we get the chance to cross paths with tons of experts from the corporate world. 

From thought leaders in HR, sales and company culture, to cutting edge creatives working in events, advertising and branding, we work with all sorts of talented individuals pushing the boundaries of how business gets done. 

Our Expert Insights series aims to bring our audience tips, tricks and wisdom from top professionals across the globe. 

We recently had the pleasure of speaking with Jared Kleinert, the CEO / Co-Founder of Offsite, a startup that’s revolutionizing the team retreat. Jared is an expert in company culture and the millennial workforce, not to mention a TED speaker, award-winning author, and USA Today’s “Most Connected Millennial.”

Jared is also the founder of Meeting of the Minds, an invite-only summit series that brings together top minds across the business community. At events in locations such as Napa Valley, Bermuda, and the Adirondack Mountains, leaders of companies generating 7, 8 and 9 figures of revenue gather to share insights and forge life-long relationships. 

In 2013, Jared was a delegate to President Obama’s Global Entrepreneurship Summit in Malaysia. As a consultant he has been hired to help companies such as IBM, Facebook and AdAge better understand their millennial workforce. 

We picked Jared’s brain about how remote and hybrid workforces can remain connected, what top companies are doing to plan meaningful in-person events, and why the company retreat is more meaningful than ever before. 

In your opinion, what is the #1 thing companies miss out on when their employees aren’t gathering in person?

Running a remote-first company is hard. 

Most remote and “hybrid” companies struggle with recruiting top talent, engaging employees, and building great company culture because they miss the human connection that offices provided us previously. 

While tools like Zoom, Slack, Asana, Notion, and 15Five, plus tried-and-true resources like email and GSuite, can make day-to-day work more collaborative and productive, over time remote teams have vulnerabilities around communication, alignment on strategy, and empathy for coworkers. While offices aren’t necessary in today’s day and age, and may actually hinder certain companies in finding and keeping top talent, “office culture” did allow people to see their teams, boss, and other work colleagues more often, allowing them to pick up on body language, hang out before or after meetings, and develop meaningful relationships. 

In 2021, and in looking towards the future of work, companies are realizing they must invest in facilitating deep, meaningful connections for their employees in new ways. That’s what we do at Offsite, helping teams plan stress-free team retreats where they have dedicated time, space, and intention to build trust, re-align on their goals, and make friends at work that will lead to increased productivity, engagement, and employee retention at home. 

How have company events changed in the last two years?

Team retreats are now, in many cases, the only times during the year that colleagues will see each other in real life. 

Therefore, the intentionality, prioritization, and ROI on planning regular offsites as a company has increased dramatically. Some companies are reinvesting almost all the funds previously allocated for office space to team retreats planned in a regular, predictable cadence such as an annual “All Hands” meeting with the entire company, and quarterly executive team or department-specific meetings. 

Given how easy it is for talent to switch jobs, slack off at home as they aren’t being micromanaged in offices anymore, and lose connection to the people and purpose of their employer, there is more reputational risk for employers around offsites (off-site company events) as well. No longer is it acceptable to bring people to a hotel conference room with dreary carpet, slow WiFi, and no flex time on the agenda to take a break, do some activities, or sneak in a workout. 

Offsites must be programmed weeks in advance to support the objectives for the team meeting, whether it’s team-building, strategic planning, learning and development, or something else. 

Offsites must be transformational, leading team members to forge long-lasting friendships at work so they can have difficult conversations in weeks and months to come, feel more inclined to work hard for their colleagues, and stick around during the growing pains in any business rather than leaving for another job opportunity. 

Offsites must be planned with feedback from your team in order to consider dietary preferences, travel sensities, blackout dates (such as weddings, milestone moments for parents, or healthcare needs), and attendee expectations for any retreat. 

What trends are you seeing for companies who are organizing in-person events for the first time in a while? What sort of goals are they hoping to accomplish?

Some companies are focused on team-building, others are focused on OKRs or strategic planning for the upcoming quarter, and occasionally we help companies plan client-facing events. Ultimately, we’re focused on helping co-founders, Chiefs of Staffs, EAs, Heads of People, and Directors of Operations especially with developing transformational experiences during the few days of the year where they can get everyone together in-person as a remote-first company. 

Most of our clients are high-growth, venture-funded startups that have doubled or tripled their headcount in the last two years and many of their employees haven’t met each other, so they are working with Offsite to support their team-building efforts. Building camaraderie in these cases allows for better collaboration and communication between departments. 

Strategic planning is another objective many of our clients are optimizing for, if they already have a quarterly OKR planning process, or want to lead department-level meetings like a design sprint, hackathon, or sales training.  

Other companies are trying to make as engaging and fun offsites as possible to, quite frankly, reduce employee churn. People are entering your company and then leaving your company, so you might want to have a great offsite experience to build the team and give them a reason not to leave.

What do you think the future of offsite events will look like if hybrid and remote work continues to remain popular?

Remote-first companies with industry-leading culture such as Basecamp, Zapier, GitLab, Automattic (which owns WordPress), Atlassian, 15Five, Buffer, and others have relied on offsites for the last decade. 

They have established a cadence for meeting in-person (typically, there’s one annual All-Hands meeting, plus quarterly executive team meetings and department-level or geocentric meetups), and so we want to support companies who already have an established cadence and help them save time, money, and stress in planning these offsites regularly. 

We also want to support newly remote companies in establishing their own meeting cadences, and educate them on how to create transformational in-person experiences because the stakes are high when building company culture as a remote-first organization. 

Over time, we will educate the market on different types of offsites, and build systems and software around ensuring those experiences are engaging and valuable as well. 

Getting your team some swag never hurts either! 😉
Thanks to Jared for sitting down with us today! Visit Offsite to learn more about how Jared and his team are revolutionizing the future of company events. Are you an industry leader that would like to be featured on our blog? Please feel free to reach out to to get in touch.