Insurance Tech
    Apr 2, 20266 min read

    How Spark Advisors Keeps Group Travel Lean and Transition-Proof with Workgrounds

    How a lean people team kept events running with just one organizer, even through a role transition, by replacing manual coordination with Workgrounds.

    Spark Advisors is a 120-person, fully remote company with co-working hubs in NYC and Denver and employees spread across the country. Being remote-first has allowed them to attract diverse, regional talent. And in-person gatherings are how they stay connected and get meaningful work done.

    So with a lean headcount, team travel should be a cinch, right? Think again. Exec meetings, company retreats, team offsites – the challenge of coordinating distributed employees for multiple events each year rivals what a much larger centralized team might face. And at Spark, like at most lean, remote-first companies, there wasn’t a whole team dedicated to making it happen.

    Spark’s dedicated travel organizer was a hospitality pro, and she began every event with the painstaking work of sourcing venues, then moved into the equally detailed work of coordinating every employee’s stay individually. When big events were close to kickoff, it was standard practice to bring in a contractor for extra support.

    With a pro organizer already in place, more headcount or expertise wasn’t the answer for Spark. They needed a tool that could turn that pro into a powerhouse. Enter Workgrounds.

    Spark’s travel organizer onboarded the AI-powered platform quickly, ramping up to planning three events in Lake Tahoe, Fort Lauderdale, and Brooklyn. Together, she and Workgrounds cut roughly 40% of the time she spent on manual work, automated front-end planning, and replaced the constant stream of change requests with a self-serve flow. Events stayed a small operation with outsized impact.

    Then the real test came. When the original organizer eventually moved on and ownership of events transferred to Jamie Stevens, VP of People, the travel function kept running smoothly because the work was already living in Workgrounds. The first major event under Jamie's ownership, Spark's March 2026 all-hands in Savannah, was the smoothest event the company had ever run.

    Here's how it happened.

    1Automating the Work Before the Work

    Starting with a search engine and a list of cities before implementing Workgrounds, Spark’s organizer would work through dozens of properties one at a time, spending hours on the phone and over email confirming availability, amenities, and rates. A shortlist took several weeks to put together.

    All of this work comes before the actual planning, and at Spark it was already eating roughly 30% of the organizer’s time on every event.

    “I remember we spent so much time in the pending stage with hotels – just waiting on a sales contact to call or email back. Hours and hours spent just chasing people down for every trip.”

    JS
    Jamie Stevens
    VP of People, Spark

    Workgrounds' automated hotel sourcing gave them all that time back. With search and filtering built into the platform, and RFPs sent and proposals filtered automatically, the organizer could get to a shortlist of vetted hotel options in a fraction of the time – often just a day or two.

    But planning a 120-person company offsite is never a one-person decision. Finance wants budget visibility, execs want to weigh in on location and feel, team leads want to make sure there’s room for teambuilding and breakouts. When sourcing moved slowly at Spark, each event’s stakeholders ended up waiting on the organizer, who was waiting on vendors. With Workgrounds, the organizer can walk into a stakeholder meeting with real options, real numbers, and a real timeline, ensuring that buy-in is never a bottleneck.

    2Change Requests Without the Middleman

    People who choose remote-first work want their travel to be as flexible as the rest of their lives. When the Spark team travels, it’s typical for employees to tack on a few personal nights to explore or add a couple of extra days for client visits.

    That flexibility used to come at a cost: the organizer's inbox. Every personal request and change to the rooming list flowed through one person via Slack DMs and email threads. When you multiply that across 120 individual attendees, the back-end management of the room block has suddenly morphed into its own full-time job.

    Workgrounds replaced that flow with self-serve. Now, rooming list management lives on the platform and attendees can adjust their own stays and handle the related charges directly, without looping in the organizer at all.

    This shift matters most in the days leading up to and during the event itself, when changes tend to spike and time is already short. Take Spark's March 2026 all-hands in Savannah, Georgia – exactly the kind of event where you'd expect a lot of guests to want to extend their stay. Instead of every change request or cancellation landing on the organizer’s desk, each guest could use their Workgrounds access to adjust their booking on their own. Unbothered by the usual cascade of Slack DMs, Jamie was free to focus on on-site needs and kicking off the all-hands agenda.

    "Savannah was the smoothest event we've run. The difference was all the little stuff that just took care of itself with Workgrounds.”

    JS
    Jamie Stevens
    VP of People, Spark

    3Continuity Through Ownership Changes

    On most lean teams, the institutional knowledge, vendor relationships, and hospitality expertise all live in one person's head. Their last day is also the day the next event starts to fall apart. At Spark, the entire event was captured and managed in Workgrounds, so the travel function didn't miss a beat when ownership shifted up to Jamie, the VP of People.

    A VP's calendar simply doesn't have room for the original organizer’s old, manual process of travel planning. That's the inherent value Workgrounds delivers: Sourcing the right accommodations and securing competitive group rates had previously required dedicated time and expertise – now it happens automatically.

    But some questions still don't automate, like how to push back on a contract clause, or knowing to ask for comped meeting space in exchange for a higher F&B minimum. When those situations come up, Jamie has a direct line to the team at Workgrounds for support.

    Transition-Proof by Design

    When ownership shifted to a new VP, the travel function didn't miss a beat — because the work already lived in Workgrounds, not in one person's head.

    4Keeping Group Travel a Lean Function Built to Last

    Since August 2025, Spark has run five events through Workgrounds, booked 611 room nights, and given all 120 employees the freedom to extend and claim their personal stays.

    5
    Events
    In 8 months
    611
    Room Nights
    Booked
    30%
    Time Saved
    Less time organizing

    Weeks of manual sourcing have been replaced by a process that delivers a hotel shortlist in days. Self-serve rooming list management keeps the constant change requests off the organizer's desk. And a real, human partnership with Workgrounds fills in what automation can't, from specific contract negotiations to on-site judgment calls. The result is an events function that runs lean and stays lean, even as the ownership role evolves.