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Why Offsite?

Offsite (offsite.com) is Airbnb for team retreats, offering a marketplace to easily book vendors for team retreats, offsites, and conferences.

We also offer end to end, “done for you” offsite planning services.

Used by hundreds of VC backed startups, Fortune 1000s and other high-growth mid market companies like Remote, HubSpot, Perplexity, Guild, and Trust&Will, among others, Offsite is already a marketplace that has facilitated close to $100M in spend on offsites, with thousands of users, and the potential to become a category-defining brand.

Offsite is looking for a founding Operations Lead to help us become more AI-native, capital efficient, and ready for scale as an already fast-growing company.

You’ll be Operations hire #1 on a team of ~40 including full-time employees and contractors, working directly with and reporting to the founder/CEO as well as our co-founders and key vendors like our outsourced accounting agency.

We need someone who has seen operational debt up-close at a fast-growing startup in the 25-100 headcount range, knows how to triage what actually matters, and builds systems that scale via automations, AI, etc without requiring constant management attention to maintain the.m

We’re VC-backed (raised $4.3M from Automattic, Forum Ventures, and 70+ angel investors including the CEOs or co-founders of Remote, 15Five, Gainsight, Vendr, ChartMogul, Invisible, and Convene), break-even (ie not burning much money), and growing quickly.

We’re also a lean-and-mean team (but actually, everyone is really nice!). This means…

As our new Operations Lead, we expect you to not only lead operational excellence from a strategy perspective, but to execute that strategy as a team of 1, leveraging AI and other automations while also putting SOPs in place for other teams to follow closely.

If you've been the first or second Operations hire at a fast-growing, VC-backed startup before where you’ve helped the company become more AI-native, meaningfully increased gross margins, and brought structure to chaos….and can do it again quickly….then this is for you!

What You’ll Own:

In the first 90 days:

• Manage and develop our Accounting and Admin Assistant — a part-time contractor who owns AR, commission tracking, contractor payments, and coordination with our outsourced accounting firm.
  • You'll become their day-to-day manager and the person who makes sure nothing falls through the cracks on the financial operations side.
• Financial reporting infrastructure: working with our accounting agency to produce reliable ARR, GRR, NRR, gross margin, and budget-to-actuals visibility for leadership.
  • The goal is a reporting package fit for a $5M-$10M/year company that leadership can act on with confidence and present to outside capital providers if needed.
• Operational state-of-the-union: We have a detailed gaps document contributed by the full team. Your first deliverable is turning that into a prioritized, owned action plan including what's broken, who owns fixing it, in what order, and what success looks like. This is a working document, not a deck.
• Operationalize our AI adoption infrastructure: working with Engineering and department leads to operationalize our internal AI strategy.
  • For example, we have a Tool Registry, a Prompt Library, and Claude deployed across the team….but adoption is uneven. You'll help change that.
• Oversee the design and development of the most important cross-department SOPs in partnership with the department leads.
  • We have strong, opinionated department leaders in each of these functions. Your job is to get them aligned on a single process and make sure it sticks.
• Clean up our tool stack (Zapier, Notion, HubSpot, ClickUp, etc) so people know where things live. Right now Notion, ClickUp, HubSpot, and Google Drive are all partially in use with no enforced source-of-truth by content type. You'll audit, decide, document, and enforce.
  • This includes getting Notion, ClickUp, and HubSpot to clean, reliable states.

Ongoing:

• Be someone our Founder/CEO can delegate to when handling operational matters and decision-making. Concretely: when a vendor payment is late, you handle it. When two departments disagree on a process, you mediate and decide. When a new tool is being evaluated, you run the assessment. When something is breaking in a workflow, you find it and fix it.
• Manage the accounting assistant day-to-day, including commission reporting, contractor invoice review, and monthly close support with our outsourced accounting agency.
• Tech stack ownership: access management, software spend audit, and keeping the stack lean. We likely have recurring subscriptions we're not using. Find them and cut them.
• Employee onboarding standardization: right now every department head onboards their own people differently. You'll build a lightweight, consistent onboarding process that works across departments without requiring a dedicated HR function.
• Lightweight recruiting infrastructure: we don't hire often, but when we do the process is manual and time-consuming. You'll set up a lightweight ATS and a repeatable interview workflow so hiring doesn't eat department lead time unnecessarily.

What you're not responsible for

Product roadmap, engineering decisions, go-to-market strategy, and revenue operations architecture.

Those are owned by department leaders.

Your job is to build the operating system that lets those functions scale.

Who You Are:

• 3-5+ years of experience, with at least 2-3 years inside a company between 20 and 100 people and ideally a tech startup that was early to embrace AI enablement internally — you know what it feels like to build something without much infrastructure beneath you
• You've owned processes end-to-end before, not just supported one….and you can point to something you built and explain how it performed in terms of increasing gross margins
• You think in systems but execute in specifics; you don't just design processes, you build them and make sure they stick
• You're comfortable pushing back on strong personalities when the process requires it; our department leads are entrepreneurial and opinionated, and they'll respect someone who comes with a clear point of view and good judgment, not just a collaborative disposition
• You have a default toward automation before process and process before headcount.
• You are “AI Native” in your approach and reach for AI and tooling before recommending a hire, contractors, or expensive software
• You're comfortable with AI tools and expect to use them daily — we run Claude across the team and you'll be expected to adopt and champion that, not just tolerate it.
  • So we know you are serious, tell us about a Skill you’ve developed and/or an Agent you’ve created in the past. We’ll expect to hear about this when you send in your resume, so we know you’ve also read the “fine print” of this application and are detailed oriented. You’d be surprised how many people miss this :)
• You're a strong written communicator — most of what you build will be documentation, SOPs, and working docs that other people actually use.

This role is probably NOT for you if:

• You've spent most of your career in enterprise or large company environments and haven't operated inside a sub-50 person company
• You need a fully built infrastructure to work within (because you're inheriting real operational debt and your job is to fix it)
• You prefer to advise rather than execute (there is no one below you to hand work to in the near term other than a part-time accounting and admin assistant).
• You're looking for a leadership team seat or a path to C-suite in the near term (this is an IC role that reports directly to the CEO, with real scope and real ownership, but not an executive position for the first 1-2 years).
• Your background is primarily RevOps or sales operations (HubSpot hygiene is in scope, but pipeline architecture and revenue systems design is not the core of this role)

Comp and Benefits:

The starting salary for this role is $90,000 - $110,000 USD (depending on experience), plus healthcare, a monthly Remote Work stipend, an annual Health and Wellness stipend, unlimited PTO, and the ability to work from anywhere.

You will also be eligible for equity options in Offsite.

💡 Interested in this role? Please complete our job application.

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