Head of Sales

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.

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.

• 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

• 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

• 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

Downtown Toronto, in person, 5 days per week

• Top-of-market OTE, plus meaningful equity at a high-growth, early-stage company
• Variable comp tied to new-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.