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Chief of StaffSMB Deal HunterRemote (North America) · Full-Time The Company SMB Deal Hunter is the go-to platform for entrepreneurs and investors buying small businesses. Our members have collectively closed over $150M in acquisitions in the past 18 months. We reach 185,000+ newsletter subscribers weekly and serve 1,000+ active members through deal origination, an off-market deal platform, a preferred lender network, 1:1 coaching, a weekly podcast, an online community, and in-person events. Our affiliated investment arm, Hunter Equity Partners, makes direct and sponsor-led investments in the small business and lower middle market, backed by accredited retail investors, family offices, and institutional investors from our ecosystem. We’re scaling fast (more members, more products, and more deals) and decisions need to move quickly and stay aligned. That’s why we’re hiring for this role. The Role This is one of the highest-leverage seats in the company. As our first Chief of Staff, you’ll report directly to the founder and operate as a true extension of the CEO, stepping into the most important problems across the business. The role touches everything: sales, operations, growth, product, and private equity. You’ll move between strategy and execution daily. Your job is to take ambiguous, high-stakes problems and turn them into structured plans, decisions, and results. You’ll do the work yourself first, build the systems to scale it, then hand it off cleanly as you take on higher-leverage work. This role is intentionally broad and demanding. You’ll learn more in one year here than most people do in five. What You’ll Own <ul><li>Be the founder’s force multiplier. Drive prioritization, prep, and follow-through so decisions don’t stall. Turn strategy into execution. When something’s falling through the cracks or a project needs someone to drive it home, that’s you.</li></ul> <ul><li>Own high-impact projects end-to-end. Step into critical initiatives across sales ops, growth, partnerships, product, and our PE arm. Push them forward and ship.</li></ul> <ul><li>Drive operational cadence. Implement dashboards, KPIs, and operating rhythms that raise the bar on accountability and clarity. Own weekly planning, progress reporting, and leadership meeting cadence.</li></ul> <ul><li>Identify bottlenecks and build AI-powered solutions. Spot inefficiencies across the business and design better workflows using AI, automation, and low-code tools. Replace manual effort with systems that scale.</li></ul> <ul><li>Pilot new service offerings and processes. Test new ideas, whether it’s a new product or service line, a new approach to investor outreach, or a better onboarding flow. Evaluate quickly, double down on what works, and kill what doesn’t.</li></ul> <ul><li>Unblock the business. Jump into live issues (pipeline bottlenecks, team gaps, member escalations, process breakdowns) and move things forward without waiting for permission.</li></ul> <ul><li>Drive cross-team communication. Capture action items, assign ownership, and ensure follow-through. Be the connective tissue between strategy and execution across growth, sales, and delivery.</li></ul> Your First 90 Days You won’t ease in. Here’s what you’ll tackle immediately: <ul><li>Hiring. Own recruiting for key roles across the business, from scoping to sourcing to closing.</li></ul> <ul><li>Coaching efficiency. Leverage AI to improve how our coaches operate, reducing manual work and increasing client impact.</li></ul> <ul><li>New product or service launch. Scope, validate, and begin building out a new AI-powered product or service offering that extends our platform’s value to members. You’ll own it from concept through early delivery.</li></ul> <ul><li>Sales team AI uplift. Deploy AI tools to score calls, surface coaching opportunities, and recover revenue gaps across our sales team.</li></ul> <ul><li>Investor intelligence. Build systems to identify and prioritize high-potential investors in our ecosystem for Hunter Equity Partners.</li></ul> Who You Are <ul><li>An entrepreneur at heart. You think like a founder. You see opportunities before they’re obvious, move on them without being asked, and take full ownership of outcomes. You’ve probably built something yourself, whether it’s a side project, a business, or a product from scratch.</li></ul> <ul><li>AI-obsessed. You don’t just use AI tools; you’re the person who finds them first, stress-tests them, and figures out how to deploy them before anyone else. You’re the one your friends and colleagues come to when a new tool drops. You see AI as the biggest unlock for every business problem you encounter.</li></ul> <ul><li>3–7 years in a startup, high-growth, or consulting environment. You’ve operated in fast-moving companies and know what good looks like.</li></ul> <ul><li>Thrives in constant context-switching. You can juggle 10+ priorities and still execute with precision.</li></ul> <ul><li>Mixes strategy with execution. Equally comfortable in board-level conversations and in the weeds (CRM, spreadsheets, tooling, whatever it takes).</li></ul> <ul><li>Data-first thinker. You know how to find signal, build dashboards, and cut through noise. Business acumen to read a P&L and understand unit economics.</li></ul> <ul><li>Communicates like an owner. Clear, concise, persuasive, both written and verbal. You can draft a sales playbook, prep a board deck, and send a crisp Slack message with equal confidence.</li></ul> <ul><li>High EQ, low ego. You work well with sales teams, external partners, and investors alike. Bias for action, fast learner, deep ownership mentality.</li></ul> Bonus: Experience with sales operations, CRM platforms, or the SMB/business acquisition space. Candidates with a business background who have self-taught technical skills (light coding, no-code tools, automation platforms) will stand out. What We Offer <ul><li>Competitive base salary depending on experience, plus significant performance-based upside.</li></ul> <ul><li>Fully remote anywhere in North America, with flexibility to manage your schedule.</li></ul> <ul><li>Direct access to the founder. You’ll work alongside the CEO daily and collaborate closely with the leadership team.</li></ul> <ul><li>Exposure across sales, private equity, product, and community. This role gives you a front-row seat to every part of building and scaling a company, including live deal flow through Hunter Equity Partners.</li></ul> <ul><li>A fast-moving, high-trust team where your work has an immediate, visible impact on the trajectory of the business.</li></ul> A Few Honest Words This role is not for everyone, and we’d rather be upfront about that. We move fast and the work is intense, closer to 8–7 than 9–5. You’ll context-switch constantly, operate in ambiguity, and be expected to identify problems and solve them without being told. If you thrive in that kind of environment, you’ll love it here. If you need defined lanes and predictable days, this isn’t the right fit. We’re building the playbook as we go, and we want someone who’s excited by that. How to Apply Send your resume and a short Loom video (2-3 minutes) to with the subject line I’m Your Chief of Staff on why this role excites you and what makes you the right person. We value clarity and directness. Show us how you think, not just where you’ve worked.

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Chief of Staff

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SMB Deal Hunter

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