💖 About Heartbeat
The next generation of entrepreneurs isn't building an Uber; they're building paid communities. These are creators, they're coaches, they're consultants that are taking their expertise and skills and then turning it into $100K, $500K, $1M revenue-generating businesses. The problem is, they’re duct-taping together tools to make this work.
Heartbeat is the OS for these service-based businesses. We bring together community, courses, payments, events and automations under one roof. We've scaled to +7,000 communities who have collectively earned $13M+ through Heartbeat.
Shopify gave entrepreneurs the tools to spin up a product-focused business in just a couple of hours & scale it massively, and we're doing the same on the services side of the industry.
🚀 Why this role matters
As Heartbeat scales, the complexity of what we’re building is growing, too. We need someone who can operate at altitude — connecting dots across teams, customers, and systems to make sure we’re executing strategically and building toward the bigger picture.
This Chief of Staff isn’t a notetaker or shadow. It’s a high-impact operator who will help architect the systems, communication rhythms, and delivery programs that turn fast-moving ideas into results. You’ll work side-by-side with the CEO on company priorities, but you’ll also take full ownership of cross-functional initiatives, helping us move with more speed, clarity, and precision.
If you’ve got the brain of a consultant, the bias for action of a founder, and the leadership chops to rally a team, we’d love to work with you.
✅ What you'll do...
🧠 Lead Strategic Execution Across the Business
Translate big-picture strategy into actionable, sequenced initiatives across Product, Sales, Ops, and Success
Own cross-functional projects end-to-end: designing structure, aligning stakeholders, and driving execution
Build scalable internal systems to make our team faster, sharper, and more aligned as we grow
🧭 Shape & Deliver Enterprise Strategy
Partner with the CEO on our enterprise accounts, leading post-sale strategy, and helping customers translate goals into real outcomes
Build a structured services layer by formalizing our agency partner network — turning one-off relationships into a repeatable delivery engine
Ensure customers see Heartbeat not just as a tool, but as a strategic growth partner
⚙️ Strengthen How We Operate
Establish team-wide communication practices, planning rhythms, and reporting systems that scale
Proactively identify bottlenecks and design systems to fix them before they become problems
Be a connective leader across functions, bringing clarity and momentum to fast-moving projects
😍 You’ll love this role if you...
Have 3–5+ years in consulting, strategy, operations, or a chief-of-staff-style role at a startup
Think like a systems designer — always looking for leverage, structure, and scalable solutions
Love getting into the details, but also know how to zoom out and orient around high-level priorities
Can confidently lead exec-level conversations with enterprise clients and internal stakeholders
Know how to earn trust across functions and lead through influence
Are energized by ambiguity, complexity, and the chance to build something foundational
🤔 A few things you might work on here…
Lead our quarterly OKR planning process, aligning the team around clear priorities, & ensuring we stay focused as we scale
Turning a fuzzy exec-level idea into a clear, cross-functional roadmap & working across teams to drive it to completion
Taking ownership of a mission-critical “floating” project (like redesigning enterprise onboarding) and building the structure to make it real
🌱 Bonus points if you...
Have worked in a founder-facing or high-growth startup environment
Have experience managing strategic partnerships, agencies, or enterprise accounts
Have built systems in tools like Notion, Airtable, Zapier, Retool, or similar
Understand the community or creator economy deeply (even if just on the side)
✨ Our Culture
Dedication to Craft. We’re each focused on becoming world-class at what we do — always learning, always leveling up.
Constantly Curious. We ask questions, explore new ideas, and seek out fresh perspectives every day.
Deeply Empathetic. We lead with understanding, knowing that listening makes us better teammates and builders.
Have fun with it. We work hard, laugh often, and enjoy the ride as we build something meaningful together.
🎁 Benefits
Competitive comp + generous equity package
Health & dental insurance
Unlimited vacation & PTO
Remote-first culture
Home office stipend
Deep ownership and a front-row seat to building something that matters
🧠 TL;DR
This isn’t a support role — it’s a builder role.
If you want to help scale a high-growth startup from the inside out, lead cross-functional ops, and architect the systems behind a breakout business… let’s talk.
Remote restrictions
- Workday must overlap by at least 5 hours with Chicago, IL, USA