Job Opening: Head Of Events

Out-Of-Pocket is trying to make the business of healthcare easier to understand. We’ve been doing this through the newsletter, courses, events, online community and more.

We’re looking for someone to take our events to the next level, handling everything from ideation to execution. We are all in on in-person events and it’s a core part of the Out-Of-Pocket strategy. 

We’re very intentional about creating spaces where the audience is curated, the event style is intimate, and the finer details are considered. We are much more focused on the substance of conversations and the experience of attendees vs. the style and glamor of the event.

The Role:

This role involves juggling several different events each year.

• Hackathons - We organize hackathons for people to build cool projects. These are full weekend affairs where teams brainstorm and meet each other, hack for 36 hours, and then we have a demo day with 150+ attendees
• Micro-conferences - We host <100 person conferences that are all breakouts and no panels. These are typically role-specific (e.g. ops knowledgefest for people in healthcare operations, healthcare data camp for data engineers/analysts).
• Sponsored Dinners - These are curated dinners that are invite-only, 20-25 executives, and involve designing a dinner experience that integrates the sponsor natively and keeps conversations interesting.
• Sponsored Happy Hours - happy hours for anywhere from 60-100 people that involve a sponsor, flash talks from people in the OOP network, and beer/food.

It’s possible we expand beyond this to even more events .

Skills Needed:

• Being one step ahead of everything -You naturally build in buffers, checklists, and “what could go wrong” reviews. You not only notice the missing chairs before the event—you’re the person who catches it two weeks earlier on the run of show.
• Creative event designer - Our events are different than most companies. We’re always experimenting on the event design itself and want your weirdest and most creative ideas that can elevate the attendee experience.
• You love to host - People feel seen and welcomed around you. You're social, proactive in connecting people, and embody the vibe we want at events. You bring charisma, presence, and confidence—this is not a behind-the-scenes-only role.
• Focused on quality - from the food vendors we use down to the types of cups we purchase, you care about each touchpoint of the attendee experience being thoughtful
• You’ve run lots of IRL events before – You’ve planned and executed real events yourself. You know what it’s like to own logistics, anticipate attendee needs, and solve problems in real time.
• Organized, both offline and online – You’re on top of timelines, budgets, tasks to be done, and every moving piece.You don’t just manage complexity; you externalize it for the team..
• You get energized by crisis (the good kind) – When things don’t go according to plan (and they won’t), you adapt and keep your cool. This is your element!

Responsibilities:

Event Execution:

• Plan and execute events from start to finish, ensuring they run seamlessly.
• Coordinate vendors, venues, and logistics with an eye for detail.
• Be on-site during events to oversee operations and tackle any last-minute challenges.

Creative Strategy:

• Collaborate with leadership to dream up new event concepts and engagement strategies for event attendees and the slack members.
• Experiment with layouts, activities, and other elements to make each engagement unique.
• Create a plan for how our events feed into the other parts of the business (e.g. content for the newsletter)
• Constantly gather feedback to refine and improve future events

Communications, Operations & Back-Office:

• Create and maintain event project plans, budgets, and timelines.
• Work with our internal team to create websites and manage the application flows (our events require an application)
• Manage the event specific content calendar, including marketing over socials, communication within slack
• Communicate with sponsors to coordinate details of their involvement
• Source and research vendors + venues within different cities.
• Track and manage event expenses to stay within budget.
• Choose tools and platforms that streamline operations (project management software, invoicing, etc.).
• This role requires strong asynchronous communication: we expect clear visibility into what you're working on, what you're prioritizing, and how you're planning to get there. Because we're remote and fast-moving, documenting your thinking is as critical as the work itself.

Qualifications:

• 3+ years of experience in event planning or project management.
• Experience managing on-site event operations and troubleshooting in real-time.
• Comfort with tools like Notion, Airtable, Google Suite, and project management platforms.
• Bonus points if you’ve worked in healthcare
• Must be able to work in the US.

Compensation and Benefits:

We offer the following: 

• $120K per year +10-20% performance bonus
• 15 days PTO
• Half of our events will be in SF, Half will be in New York, and occasional events will be in other cities. This will require travel for 4-5 weekends a year. Occasional site visit travels may also be required.

To Apply:

Send the following to events@outofpocket.health:

• Your resume
• A paragraph about the best event you’ve been to and why (doesn’t have to be a professional one)