Heartbeat

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Chief of Staff

  • Growth
  • Full-time
  • Remote
  • 90K - 110K USD a year

Posted on July 30, 2025

💖 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