Tailscale 首届 TailscaleUp 客户大会在旧金山 SFJAZZ Center 举办，300 人参会

The inaugural TailscaleUp took place Aug. 26 at the SFJAZZ Center.Photo: Cole Group

SAN FRANCISCO—When Tailscale's C-suite floated the idea of a flagship customer conference, the company had no live event branding, no historical event photos, and no event agency. Fast forward 14 months to this past August, and the software development company filled San Francisco's SFJAZZ Center with 300 attendees for its inaugural, one-day TailscaleUp.

On Aug. 26, the event brought together engineering, security, and IT leaders for a deep dive into secure connectivity (the company's specialty). The customer conference was designed to be the Tailscale brand experience personified—technical, community-driven, and highly intentional. The program blended educational sessions, hands-on workshops, live demos, networking, gamification, and a "dark mode"-inspired after-party.

"With this being our first year, our community and customers didn't know what to expect," said Hillary Foster, Tailscale's head of events. "They didn't know whether or not it was worth coming to, right? So we had to show up, show up really well, and give everybody FOMO, so that the next time we do it, everybody wants to go."

She added, "We really built an operating and planning structure from scratch" across the company's departments.

Photo: Cole Group

The budget could not accommodate a full event agency partner, so with her background, Foster built one. "We weren't able to budget agency support, so we had to create our own agency through our networks and hiring individual freelancers," she said. "It was an awesome, scrappy team that put this together, and I'm really proud of what we did."

The anchors of the conference included a main stage, which livestreamed the keynote session; a hands-on workshop room; and a double demo station set up in the lobby, where attendees could talk to Tailscale experts and get questions answered. A "zero day" community event also took place on Aug. 25, when 50-60 of the company's "home labbers" (aka Tailscale's strong home user community) gathered, with some even leading their own sessions.

Photo: Cole Group

The conference culminated in an evening after-party, dubbed TailscaleUp After Dark, at The Hibernia, a historical event venue in San Fran. Foster said this is where all of the event's branding went "dark mode." The after-party was also an ideal way to incorporate more sponsors, since the conference didn't include any kind of expo, she explained. The party was also open to the wider tech community in SF, which proved to be a successful way to funnel more ticket sales into the daytime conference.

"About 100 ticket registrations came from that path," Foster said. "We were also able to engage a lot of different partners as sponsors who were really interested in attending. They were also able to bring more people who might not've had interest in attending a conference all day, but wanted to interact with Tailscale in some way."

Other fun touchpoints: sustainable tote bags made from recycled materials as swag and a build-your-own keycap station, where attendees could choose between colorful, Tailscale-branded keycaps to turn into fidget-friendly keychains.

Photo: Cole Group

"These have been making their rounds for awhile now in the tech world," Foster said of the fidget clickers. "The fun part about those keycaps is that they are real keycaps, so attendees can put them on their actual mechanical keyboards."

Her lessons learned for other event profs: "If it's your first time doing a customer conference, make sure that you have very clear goals for what you want this conference to achieve." Tailscale set five trackable goals and got leadership to sign off alongside the budget.

Foster also got the word out internally. She held all-hands presentations on why the event mattered, why it was happening, and what to expect.

Photo: Cole Group

"That got the entire company rallying behind it," she said. "Once you define those goals, make sure everybody knows about it, not just leadership, so that everybody in your company is invested. Sometimes people look at events as frivolous, when in reality they're a huge engine for revenue expansion."

Foster added that the company is still analyzing the ROI, but said they're looking at things like attendance and the types of expansion or net new deals that came out of the event. As for what this event will look like next year, that's still up in the air, Foster said. "A roadshow format has been floated, since we do have a global customer base."

Keep scrolling to see key vendors and more from inside TailscaleUp with insights from Foster...

VENDORS

Animations: Video Armada
Catering: Foxtail
Creative Director: Chelsea Kelly
Fabrication/Scenic: Hill & Partners
Hotel Partner: The Proper Hotel San Francisco
Housing Block Support: Meetings Made Easy
Keycap Fidget Activation: Goblintechkeys
Photographer: Cole Group
Producer: Kelly Marlow
Swag/Merchandise Partner: Creative Solutions
Venues: SFJAZZ Center, The Hibernia
Water Bottle Activation: Fill it Forward

TailscaleUp and its 300 attendees took over the SFJAZZ Center. Photo: Cole Group

The main stage keynote was livestreamed and posted onto YouTube. Photo: Cole Group

All other workshops and breakouts were also recorded and will gradually be uploaded to YouTube. "We really wanted to focus on that in-person, hands-on experience," Foster said about why this didn't become a hybrid event. Those recordings will, instead, become valuable evergreen content for the company to post throughout the year. Photo: Cole Group

These custom tote bags made from recycled materials served as handy swag. Photo: Cole Group

Swag also included these Fill it Forward water bottles. (Humble brag: Foster said she discovered Fill it Forward at a BizBash/Connect event!) Photo: Cole Group

Attendees could also pick out colorful branded stickers for their badges or water bottles. Photo: Cole Group

The evening after-party took place at The Hibernia, a historic landmark that was built in 1892 as a bank. Photo: Cole Group

Foxtail was on hand as caterer with cheeky F&B stations like this "cheat day every day" dessert bar. Photo: Cole Group

Light-up beverages were also on offer. Photo: Cole Group

About the Author

Editorial Director

Sarah Kloepple is the editorial director for BizBash and has been with the brand since 2022. She previously held editor roles at Meetings Today and St. Louis Magazine.