Head of Sales
At a glance
Leadership Sales Leadership role at Kick. Toronto · full-time.
Pay not stated
Growth Roles summary, based on the employer's posting.
What you'll do
- Coach four Account Executives while personally joining deals and turning successful approaches into repeatable sales practices
- Create the selling framework, deal stages, forecasting process, and playbook reps will follow
- Build GTM recruiting, RevOps, and sales enablement from the ground up
- Lead complex sales with the largest fifty accounting firms, coordinating across multiple decision-makers
- Use activation feedback with Customer leadership to improve qualification and bring AI agents into sales workflows
What you bring
- At least seven years selling B2B SaaS or services, or running a business, including three years managing sellers
- You have built a high-volume sales motion from zero rather than taking over an established system
- You have personally set pipeline stages, forecasting methods, and conversion measures, with strong RevOps judgment
- You have changed target-customer or qualification standards using post-sale and activation evidence
- You actively use AI in your work and can explain which sales tasks should be automated versus kept human
Who this fits
This suits a player-coach who can rescue a live deal, coach the rep afterward, and build the operating system around the team. You will manage four Account Executives initially while growing the sales organization, with a stated path toward broader revenue ownership. The role is based downtown in Toronto and requires working in person five days each week.
From the employer
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
- Implement and enforce a sales methodology, coaching reps to become better sellers
- Design and enforce sales stages and a playbook
- Stand up and own GTM Recruiting, RevOps and Sales Enablement
- Personally drive 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.
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