About the Role

As our Engagement Program Lead, you'll own how Parachute comes together. You'll run the logistics and execution behind our employee programs including company offsite, our department and team gatherings, the moments where a remote-first company creates in-person collaboration to accelerate working relationships and shared learnings. You'll also keep our People & Culture programs running day to day, so they land on time and feel considered.

We're roughly 320 people and growing fast, which makes the scale of this work real: our annual company offsite now brings the whole company together, and department gatherings are multiplying faster than any one person can plan them. A big part of your first year is standing up Offsite-in-a-Box: a set of vetted vendors, templates, and budget tools that lets any department lead plan a great gathering without starting from scratch. This role sits at the center of two things we care about: making in-person time count, and making it easy for teams to create it themselves.

About the Team

People & Culture at Parachute is a small, senior team with a growing bench behind it. One side of the function owns how we organize, how we hire and pay, and how the function runs day to day. The other side owns what happens after someone joins: engagement and organizational insight, leadership and manager capability, and the moments that bring a remote-first company together.

You sit on the Employee Experience & Development side, reporting to the VP who owns the strategy and design of these programs. 

The People & Culture team is growing with expanded programming and responsibilities, which means the systems you build become how we operate — and there is room to grow with the function.

Key Responsibilities

Company events and offsites

• Company offsite: Own end-to-end logistics for our annual company offsite including venue and vendor sourcing, contracts, travel and rooming, run-of-show, on-site execution, and post-event reconciliation
• Department gatherings: Support department leads planning their own offsites with sourcing, budget guidance, and a sounding board on agenda and logistics
• Spend discipline: Track spend in real time against event budgets and reconcile with Finance after every event
• Contract and vendor governance: Route vendor agreements above our signature threshold through Legal, and hold every vendor to W-9, certificate of insurance, and indemnification requirements before signature. No employee or confidential company data goes into event vendor tools.
• Duty of care: Own traveler safety, emergency protocols, and accessibility requirements for company-sponsored travel and on-site events.

Offsite-in-a-Box

• Build the toolkit: Own the intake form, planning templates, vetted vendor agreements, and budget calculator that let department leads run their own gatherings, maintained as a documented, current library you are the named steward of — structured so it can serve as context for our AI tooling, not just a shared drive folder
• Onboard planners: Bring planners into the process and collect the post-event one-pager from each gathering
• Iterate: Refine the toolkit each quarter based on what planners tell you is missing or getting in the way
• Automate the coordination: Use AI tooling to take coordination time out of the process: intake triage, vendor comparison, first-draft budget reconciliation, and post-event synthesis. The tenth department gathering should take materially less of your time than the first.

Program administration

• Approvals: Run the budget approval workflow for gatherings that fit within policy, escalating only the exceptions
• Program calendar: Coordinate logistics, communications, and scheduling for company-wide People & Culture initiatives (e.g., engagement survey launches, manager program scheduling, and recognition fulfillment)
• Recognition: Own recognition and swag fulfillment end to end, including vendor management for our swag store. You'll partner closely with our Celebrations & Community lead on the recognition and celebrations calendar: program design and criteria sit with that lead and the VP, while execution, logistics, and vendor relationships sit with you.
• Scale: Build and refine processes that hold up as the company grows

Inclusion & Belonging Council

• Turn ideas into events: Partner with our Inclusion & Belonging Council to translate what they want to do into a real calendar, a real budget, and bring events to life
• Remove the friction: Handle logistics, vendors, communications, and scheduling so Council members can spend their energy on content and community rather than coordination
• Reach everyone: Make sure programming works for Parachuters regardless of where they sit geographically track participation for hub versus non-hub Parachuters so the gap stays visible and closing
• Close the loop: Track participation and feedback, and bring it back to the Council so the calendar gets better each cycle

Measurement

• Track what matters: Attendance, utilization, cost per attendee, and post-event feedback across the program, split hub versus non-hub
• Quarterly read: Turn that into a simple quarterly summary that tells us what is working and what to change
• Tie programs to engagement: Evaluate gatherings against movement in the connectivity and belonging sub-scores of our engagement survey, not attendance alone. Cost per attendee only means something next to the engagement lift it bought.

Requirements

• 4–6 years in event program management, employee experience, or a related operations role
• You have owned a multi-day offsite or large company event end to end, for 300+ people, including the budget
• Vendor confidence. Comfortable sourcing vendors, negotiating a contract, and holding a vendor to what they committed to
• Real budget ownership. Tracking spend as it happens and reconciling cleanly with Finance
• Strong organizational skills, with the ability to manage multiple workstreams and deadlines simultaneously
• Clear written and verbal communication; comfortable updating stakeholders at different levels
• Judgment with confidential information — you will sit close to sensitive People & Culture work
• AI fluency. Daily, active use of AI tools (e.g., Claude, ChatGPT, Notion AI) — and evidence you have used them to take real work off your own plate, not just familiarity with them
• Proficiency in project management tools and software (e.g., Asana, Jira, Notion, Google Workspace)
• Desire to work in a startup environment with a proactive and hungry mindset, and able to pivot quickly based on company needs
• Willingness to travel (approx. 10-20% travel) for on-site execution of annual offsites, regional team gatherings and general venue sourcing. 

Nice to have

• Experience supporting a remote-first or distributed workforce
• Experience supporting an employee resource group, culture council, or other employee-led group
• Familiarity with offsite planning platforms or vendor marketplaces
• Healthcare or health tech experience

Benefits

• Medical, Dental, and Vision Coverage: Comprehensive plans with options for low-to-no-cost premiums
• Employer HSA Contribution: Company-funded contributions to your Health Savings Account
• 401(k) Retirement Plan
• Equity Incentive Plan
• Annual Company-Wide Bonus: Opportunity for up to 15% bonus based on company performance
• Remote-First Culture: We are remote-first with a dedicated NYC office and reimbursement options for co-working spaces
• Flexible Vacation Policy
• Summer Fridays: 5 additional Fridays off during the summer (separate from PTO)
• Home Office and Wellness Stipend
• Monthly Internet Stipend
• Annual Learning and Development Stipend

Base Salary Band (based on experience and level)

$85,000-$110,000