The Company
SMB Deal Hunter is the go-to platform for entrepreneurs and investors buying small businesses. Our members have collectively closed over $200M in acquisitions.
We reach 200,000+ newsletter subscribers weekly and serve 2,000+ 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. HEP has deployed over $15M over the past 6 months.
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 a roll-up-your-sleeves kind of role for someone who gets sh*t done.
As our first Chief of Staff, you'll be the founder's right hand. You'll context-switch constantly (from editing a newsletter draft to setting up a Zapier automation to following up with investors on a deal), and you'll do it without needing someone to hold your hand.
The job: take things off the founder's plate so she can focus on the highest-leverage decisions in the company. That means being resourceful, fast, and comfortable operating without a playbook.
What You’ll Own
- The founder's to-do list. You take things off her plate across growth, sales, ops, product, and our investment arm, and make sure they get done fully, correctly, and on time.
- Follow-through. You're the reason action items don't disappear after a meeting. You track them, chase them down, and close them out (whether that's with the dev team, an investor, or a vendor).
- Workflows and systems. When something is slow or broken across the business, you fix it - using AI, automation, and low-code tools to make it scale.
- Projects from start to finish. From a new product feature to a marketing campaign to a deal room, you don't hand things off and hope for the best. You own them until they're done.
- New initiatives. When we want to try something new, you help get it off the ground: research it, set it up, and keep it moving.
What You'll Actually Do
No two weeks look the same. Here's a real sample of what lands in this role:
- Edit and publish newsletter editions, including writing, formatting, and QA before send
- Refine YouTube scripts and marketing copy across email, LinkedIn, and X
- Build and update automations in Zapier
- Keep the CRM clean and current
- Draft investor communications and set up deal rooms
- Review investment decks and flag key questions
- Research, build, and launch lead magnets to grow our audience and member base
- Communicate with our dev team to ship new platform features and report bugs
- Scope new feature sets and translate business needs into clear requirements
- Follow up relentlessly, with investors, partners, vendors, and internal team members until things are closed out
- Support webinar and workshop execution (from prep and materials to post-event follow-up)
- Support hiring end-to-end (write the job post, screen candidates, and run first-round calls)
- Spot inefficiencies across the business and build better workflows using AI, automation, and low-code tools
- Jump into live issues (pipeline bottlenecks, process breakdowns, team gaps) and move things forward without waiting for permission
Who You Are
- Entrepreneurial by nature. You've either started something yourself or been an early hire somewhere where you had to figure everything out. You're used to operating without a net.
- Moves quickly. You have a bias for action. You'd rather ship something great today than something perfect next week.
- High standards, not a perfectionist. You care about the details that matter and let go of the ones that don't.
- Organized and on top of it. You can juggle multiple open projects across different parts of the business without dropping the ball.
- A clear, confident communicator. Written and verbal. You can draft an investor update, a job post, and a Slack message to the dev team (all in the same afternoon).
- Tool-savvy. You know your way around CRMs, email platforms, automation tools, and AI. You pick up new software fast and don't need hand-holding.
- Low ego, high output. No task is beneath you. You take ownership, follow through, and care about the quality of your work.
- Comfortable with ambiguity. You don't need a perfect brief to get started. You ask the right questions, make reasonable assumptions, and move.
- Leads with data. You don't go on gut alone. You know how to pull the numbers, read them, and act on them.
- AI-forward. You use AI tools in your day-to-day and know how to apply them to real business problems, not just as a novelty but as a genuine productivity unlock.
Background
3–6 years of experience across structured, high-standards environments (investment banking, consulting, private equity) and fast-moving ones (startups, agencies, high-growth companies).
You know how to think carefully and act quickly, and you know the difference between when each is called for.
What We Offer
- $120,000 – $150,000 CAD depending on experience, plus bonus - structured as an independent contractor engagement
- Fully remote anywhere in North America, with flexibility to manage your schedule.
- Direct access to the founder. you'll work alongside the CEO daily and have real influence on how the company operates.
- Exposure across growth, sales, product, community, and private equity. This role gives you a front-row seat to every part of building and scaling a company.
- A small, high-trust team where your work is visible, your impact is real, and nothing you do gets lost in a bureaucracy.
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 [email protected] 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.