Head of Events & Offsites

About the Employee Experience Team

At Thumbtack, we believe a thriving team is the foundation of a thriving business. As an award-winning virtual-first (not virtual-only) company, we’re intentional about ensuring our Team members feel connected, cared for, and empowered no matter where they’re working from. That’s why our Employee Experience (EX) function isn’t just a nice-to-have, it’s a core part of how we operate. Embedded within the People org, our EX team is behind the moments that make work feel meaningful. We create in-person connection opportunities, build thoughtful recognition programs, and support holistic wellbeing in ways that truly matter to people, rather than just ticking a box.

About the Role

As Thumbtack's internal events function enters its fifth year, we're seeking an exceptional events leader ready for their next big challenge: elevating a program that creates purposeful, business-aligned in-person experiences for our 1,000+ distributed employees. In this role, you'll lead 50+ annual gatherings–ranging from intimate leadership offsites to 500-person company events–and managing the annual events and offsites budget to deliver high-impact, meaningful experiences that drive engagement and business outcomes. You’ll lead a small-but-mighty global team of event managers and coordinators, ensuring every gathering is executed with operational rigor, financial discipline, and a focus on what truly matters.

Here's what makes this role unique: you'll have real influence over how thousands of employees experience our culture, but you'll need to earn that impact through exceptional execution, fiscal rigor, and a deep passion for your craft. The scope is significant, the timeline expectations are ambitious, and the quality bar is high because these gatherings are strategic business tools that drive alignment for our distributed workforce. We need someone who gets genuinely excited by complex operational challenges and thrives when given ambitious goals with the autonomy to achieve them your way. If you're most comfortable maintaining existing programs or prefer roles where someone else defines the "how", this isn't the right fit. If you're energized by work where you can see direct impact and you take extreme pride in your bar for excellence, let’s chat.

What you'll do

• Event Planning & Execution: work alongside your team to execute 50+ annual in-person employee gatherings ranging from 5-person executive offsites to 500-person employee conferences, managing every detail from venue sourcing to on-site logistics and post-event follow-up.
• Drive Impact Through Excellence Lead: Architect and continuously improve the operational backbone of our events engine by building scalable planning workflows, playbooks, and automation systems that ensure consistent quality across your portfolio and maximize your team's efficiency.
• Financial Stewardship: Build and manage the annual in-person event & offsite budget with precision and a bias for impact over optics, owning 12+ month forecasting, event-level P&Ls, and cost-per-head optimization.
• Lead with Autonomy and Accountability: Manage and develop a global team of event managers, coordinators, and contractors across the US and Philippines, setting clear expectations and providing growth pathways in a fast-paced and high-performance environment.
• Executive & Cross-Functional Alignment: Drive collaborative partnerships and cross-functional alignment with Departmental Leaders, Finance, Communications, Legal, and Executive Admin teams, translating leadership vision into impactful and executable event plans with tight timelines.
• Vendor Strategy & Partnerships: Establish and manage scalable vendor partnerships (e.g. venues, airlines, production companies) that unlock long term efficiencies, reduce costs, and ensure high-quality, consistent execution across all events.
• Own the Details That Drive Results: Establish measurement frameworks and feedback loops to track planning lead times, participant satisfaction, budget efficiency, and team velocity, using data to drive continuous improvement

In order to be successful, you must bring

• 8-10 years leading large-scale employee events in fast paced, high growth environments with experience being in-house (agency background is a plus but not sufficient alone). You must have expertise in multi-day offsites and company-wide gatherings (think leadership retreats, multi-day team offsites, and all-company strategic planning conferences - not holiday parties, lunch & learns, weddings, or single-day events). You must know the nuances/complexity of large-scale domestic travel, overnight accommodations, multi-session agendas, complex F&B programs, and creating experiences that drive business impact.
• Proven track record owning and managing event budgets with precision; able to forecast 12+ months out and confidently deliver to budget targets, not just estimate around them.
• Hands-on leadership of globally distributed teams with experience managing across US/international time zones while maintaining high performance standards and coaching mindset.
• Systems building and process optimization expertise where you've created scalable operational frameworks, automated workflows, and measurement systems that connect people, process, and performance outcomes.
• Exceptional communication and influence skills that enable you to drive effective partnerships and alignment across cross-functional teams, hold others accountable, and clearly articulate decisions and tradeoffs when stakeholders have competing priorities.
• Tech-forward mindset and early adoption of AI/automation tools by actively leveraging platforms like Slack, Swoogo, Navan, and especially AI tools like Gemini and ChatGPT to multiply your team's capabilities and streamline event operations.
• Willingness and ability to travel 5-10 times per year domestically and once annually to the Philippines.

Expected salary ranges

• For candidates living in San Francisco / Bay Area, San Jose, New York City, or Seattle metros, the expected salary range for the role is currently $180,000 - $220,000.
• For candidates living in Austin, TX or Washington DC metros or in California, Massachusetts, New Jersey, or Washington states, the expected salary range for the role is currently $160,000 - $200,000.
• For candidates living in all other US locations, the expected salary range for this role is currently $153,000 - $187,000.

Actual offered salaries will vary and will be based on various factors, such as calibrated job level, qualifications, skills, competencies, and proficiency for the role.