About Kick

Kick's mission is to automate the boring stuff for the 35+ million US business owners and their accounting firms, so they can focus on what matters most. After selling his prior company, Teachable, for $250M, Kick founder Conrad Wadowski wanted to take on a bigger mission. Our team is a fast‑growing group of top performers from McKinsey, Shopify, NASA, and others, building the future back office together. Kick has raised $20M from OpenAI, General Catalyst, and Google Ventures, and is quickly becoming the #1 AI‑native accounting platform of choice for growing firms.

About the Role

As Head of Sales, you'll lead a team of 4 Account Executives and growing. You will build the repeatable, scalable SMB‑to‑Enterprise motions that scale us to $100M+ and beyond, taking a chunk of QuickBooks' $13 Billion business. To start, this is a true player‑coach role: you'll be in deals, building the playbook, and scaling the team, while standing up RevOps from scratch, with a clear path to SVP of Revenue owning pre‑ and post‑sales as the business grows.

What You'll Do

- Build the repeatable SMB accountant sales motion: discovery, qualification, stage definitions, conversion metrics, weekly forecast cadence
- Coach AEs live on calls, ride along on real deals, and carry your own bag where it accelerates the team
- Stand up and own RevOps fundamentals: pipeline architecture, attribution, leadership and investor reporting
- Personally drive our first 1‑3 enterprise deals with Top 50 accounting firms (multi‑threaded, multiple stakeholders)
- Partner closely with our Head of Customer on activation feedback, selling the right deals rather than just the most deals
- Drive AI‑native sales by bringing agentic capabilities into the workflow to compress rep headcount needs as we scale





Ideal Candidate

- 7+ years in B2B sales or entrepreneurship as a business owner selling SaaS or services, with at least 3+ years leading a sales team
- Has scaled a high‑velocity sales motion from scratch, not inherited an existing playbook
- A player‑coach by default: comfortable jumping on a live call to save a deal, then debriefing with the rep
- Strong RevOps instincts; has personally designed pipeline stages, forecast process, and conversion metrics
- Has explicitly changed ICP or qualification criteria based on post‑sales/activation data
- Personally uses AI in their workflow today (Granola, Clay, Gong‑style agents, etc.) and has a point of view on what to make agentic versus what should stay human

Bonus If You Have

- Sold into accountants, bookkeepers, or accounting firms (e.g., Xero, Gusto, Pilot, Float, Bill, Ramp, Brex)
- Scaled a sales team from 2‑3 reps to 15+
- Built or shipped agentic / AI‑native sales capabilities, not just used vendor tools
- A background blending consulting, banking, or strategy with a frontline AE chapter

Location

Downtown Toronto, in person, 5 days per week

What We Offer

- Top‑of‑market OTE, plus meaningful equity at a high‑growth, early‑stage company
- Variable comp tied to recent‑logo accountant deals and activated ARR
- Employee‑friendly equity: QSBS eligible, early exercise, extended exercise window
- Medical, dental, and vision benefits (employee + dependents)
- Apple laptop/headset, health and commuter stipends
- Regular team meet‑ups in Palo Alto, plus a dedicated Toronto office

We're building a world‑class team of creative thinkers and doers from diverse backgrounds. If you're excited by this role, even if your experience isn't a perfect match, we'd love to hear from you.

📌 Head of Sales (Toronto)
🏢 Kick
📍 Toronto