When a fast-growing tech company decides to celebrate its people, the planning load usually lands on whoever has bandwidth that week. For Automotus, which helps cities manage curbs and cut congestion, that responsibility fell to Kelly Schmandt Ferguson, Chief of Staff, after a heavy year. Their Santa Monica retreat shows how purposeful team retreat planning can turn a weekend into a cultural reset.
Automotus’ story speaks to teams from San Francisco to New York and Denver who run hybrid schedules and want more in-person connection without burning internal capacity. The choices they made reveal clear tradeoffs between DIY corporate event logistics and bringing in specialists so leaders can focus on strategy.
why they picked santa monica and malibu
Location matters. Santa Monica and nearby Malibu gave Automotus easy access for most of their West Coast staff while offering outdoor options that feel natural instead of forced. A beach volleyball match, a bike ride on the Strand, and a vineyard tour in Malibu created moments that matched the team’s energy better than a downtown conference center would have.
There is also practical strategy at work. Automotus deploys its curb technology in specific cities, so planning offsites in markets where their product runs—Los Angeles, Phoenix, or Chicago—can double as customer empathy tours. That alignment—seeing the product operate on a real street and then celebrating the team that built it—deepens purpose in a way a generic venue never will.
the hidden cost of DIY planning
Leaders often underestimate the invisible costs of internal event planning: dozens of vendor calls, back-and-forth emails, and mental load on someone who should be doing higher-value work. For a Chief of Staff, fifty hours of coordination is fifty hours lost to strategy, hiring, or priority projects.
That calculus pushed Automotus to a dedicated event design service. An Event Designer took on vendor negotiation and day-of logistics so company leaders could show up as participants and culture owners rather than administrators.
the pace framework for better offsites
Automotus used a simple model we call PACE: Purpose, Activity mix, Connection moments, and Energy management. Purpose makes the goal clear before booking anything. Activity mix balances high-energy options like beach volleyball with lower-key moments like a wine tasting or a bike tour along the coast. Connection moments are the unscripted buffers where real bonding happens. Energy management sequences the days so high-intensity activities do not follow one another.
For teams in New York or Miami thinking through a two-day retreat, the PACE approach scales: open a day with a shared physical activity to break hierarchy, follow with a relaxed dinner for conversation, hold a short morning values session, then close with a low-key communal activity that requires presence but not effort.
Teams wanting more examples can explore more workplace insights about activities that work for mixed groups and can check read more articles on the Naboo blog for formats used in markets like Las Vegas, Washington, and the Rockies.
common planning mistakes
- Choosing impressive activities that do not match team preferences
- Overpacking the schedule without breathing room
- Measuring success only by flawless logistics instead of real connection
- Skipping a short values or alignment conversation
how to measure success
Offsite returns are often qualitative and delayed, so track a mix of leading and lagging indicators: participation and engagement at the event, post-event satisfaction scores, new cross-team conversations, and whether decision language becomes more consistent over the following quarter. For Automotus, immediate wins were high participation and visible energy at the close; the cultural lift showed up in smoother collaboration in the months after.
keep hybrid work healthy
Automotus values remote flexibility, yet the team chose in-person moments deliberately. The question for leaders is not remote or in-person but what work benefits from being together. Annual or semi-annual offsites, planned with intention and the right support, accelerate relationship depth and make remote collaboration more effective.
delegate logistics to protect capacity
The clearest insight from Automotus is simple: the people who add the most meaning at an event are not usually the best people to run the logistics. Bringing in specialists protected senior staff time, let leaders participate as humans rather than coordinators, and produced an event that felt intentional instead of over-managed.
frequently asked questions
how far in advance should we start planning a two-day retreat?
Six to eight weeks is a practical minimum for a two-day retreat with multiple venues, but twelve weeks gives better options. Working with a specialist can compress that timeline by removing the research phase.
what activities work best for mixed-experience teams?
Pair a physically active option with a relaxed social one. For example, a beach volleyball game plus a vineyard visit or a guided food tour gives multiple ways for people to connect.
how do we justify the cost to leadership?
Frame the cost in terms of what it protects: leader time, faster alignment, and improved collaboration. The cultural returns are often larger than the per-person price tag when you account for reduced context switching and stronger team momentum.
what difference does an event platform make?
Specialists bring pattern recognition. They have seen pacing mistakes and vendor issues before, so they plan to avoid them. The result is smoother execution and more time for leaders to focus on content instead of coordination.
how do we include values without it feeling like work?
Keep the session short, forward-looking, and in a relaxed setting. Framed as a shared reflection inside a celebratory weekend, a values conversation lands as meaningful instead of mandatory.