Head of Sales

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 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.