Bringing it Together at our TT Connect North America and Philippines Offsites

Thumbtack People Team
Life @ Thumbtack
Published in
6 min readJul 18, 2023

By: Sophie Yoo, Senior Manager, People Programs

It’s been two years since we officially introduced Thumbtack’s virtual-first, not virtual-only working model, and we’re continuing to anchor in our commitment to flexible work coupled with in-person connections. We believe that meaningful face-to-face connection helps us to foster deep relationships and build community. That’s why in-person gatherings are a foundational component of our working model — there’s power in building relationships in real life.

Across North America and the Philippines (TPH), more than 820 Thumbtackers came together for our first “TT-Connect’’ in-person gatherings of the year in Berkeley, CA and Manila, Philippines. The events’ theme, “Bring it Together,” reinforced the “why” behind our virtual-first, not virtual-only working model — in-person connection. Together, we bonded, laughed, learned more about one another, and celebrated the people and work that make Thumbtack, Thumbtack. We’re excited to share our favorite moments and what the event was like for Thumbtackers, some of whom attended for the first time.

Celebrating past, present and future

Each event kicked off with a “TT-Connect Welcome Dinner and Reception” hosted by leaders who shared a special toast that reflected on our journey as a company as well as some of the exciting things ahead! Teams mingled, caught up over dinner, cocktails or mocktails, then enjoyed late-night events like sugar skull painting, “bingo & brews,” and board games.

Bonding time & team breakout sessions

Day 2 was full of exciting events, beginning with morning activities like pilates and circuit training hosted by Thumbtackers. From there, official programming kicked off with a special “Ask Me Anything” session with our CEO, Marco Zappacosta, followed by a series of team breakout sessions tackling the topics and projects most impactful to each team in H1. For our G&A teams, this included the first iteration of our Diversity, Equity, Inclusion and Belonging 101 training.

In the early afternoon, Thumbtackers participated in “Choose Your Own Adventure” style activities hosted by our Employee Resource Groups such as assorted lawn games, board games and DIY activities, like creating lip scrubs and sensory water bottles.

Later that evening, everyone came together for a themed cocktail party and dinner that included awards & recognition. Thumbtackers dressed as their favorite category on the Thumbtack app or in their best Thumbtack swag or onesies. Our nighttime festivities were a hit — Thumbtackers sang their hearts out at karaoke (there were even some team vs. team “sing-offs”), bonded at a neon party, enjoyed “all you can eat’’ late-night bites or simply kicked back and caught up with coworkers.

Our 2022 North America Values Award Winners even came together for a special dinner with our Senior Leadership Team to celebrate them and how they represent and live Thumbtack’s values every day.

Favorite moments & personal highlights

So, what do Thumbtackers have to say about their experience? We caught up with 2 attendees to get their personal highlights and how the event fostered a sense of connection with their teams.

Arvie Angeles (he/him), Manager II, Trust & Safety Proactive, Works and lives in Manila

My personal highlight from the offsite was the Trust & Safety Team’s team breakout session, where we participated in the “Dress Up Your Manager” contest. It was truly amazing to see the level of teamwork and creativity displayed by all the teams as they transformed recycled materials into impressive superhero costumes. The competitive spirit among the managers was infectious, and I am thrilled to share that our team emerged as the champions of the contest.

The offsite event was an incredible opportunity for our team to bond and connect with our colleagues through enjoyable activities such as dinner, games, and workshops. During dinner, we had the chance to have meaningful conversations and get to know each other on a personal level, which is rare in our remote setup. It was a valuable time for me to connect individually with each of my team members, forging stronger relationships beyond our coaching sessions. I also made new friends from different teams, which is quite challenging in a remote environment.

Misha Garg (she/her), Head of People Data Science, Works and lives in Boston

My favorite activity at the offsite was the Team breakout sessions! Connecting with my core stakeholders over key business challenges was very rewarding. It allowed us to cover significant ground in a few hours and come out with a lot of great information that is helping us to move faster in a virtual setting.

This was my first big company offsite at Thumbtack and wow! I was not disappointed. I found that both structured and unstructured time was very intentionally planned and effective in helping us build deeper relationships. The unstructured time was great — I bumped into so many people that I had only met virtually until the offsite and we ended up connecting on a variety of topics from personal life to specific work projects.

A look ahead — Local Community meet-ups, team events & more

As our first in-person gatherings of 2023, our H1 offsites proved to be both invigorating and full of laughs, connection and celebration. As we look ahead, we’re excited to embrace ways in which we can deepen our relationships through in-person events like local community meet-ups, team gatherings, and more. Stay tuned for updates as we continue to live out our virtual-first working model coupled with in-person connection and events.

We’re hiring inspired folks who want to embrace the virtual-first, not virtual-only way of working. Check out opportunities to join at www.thumbtack.com/careers.

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Thumbtack People Team
Life @ Thumbtack

We spend our days empowering people from all walks of life to do their work with joy and purpose. Read more about the work we’re doing, and how we’re doing it!