Founding Outbound Lead

Kick is an applied AI company building the first self-driving bookkeeping experience. We've raised $20M from OpenAI, General Catalyst and Google Ventures to help millions of Business Owners and Accountants automate the boring stuff, so they can focus on what matters most.

You’ll build Kick’s outbound motion from the ground up. We’re building Kick’s outbound motion to be a case study in excellence for this function (Rippling, Ramp, etc.). That means building a revenue machine with a human touch that strengthens our customers’ Kick experience from the first touchpoint. As an applied AI company, our outbound should be at the frontier of how AI can improve the customer experience.

• Own meetings booked with US accounting firms, across cold outbound and warm MQL follow-up
• Build cold outbound from scratch: pick target firms, source and enrich lists with AI workflows, write sequences, and dial yourself alongside AEs, daily, until you know what lands
• Work warm intent fast by running call sprints on new MQLs, webinar attendees and sign-ups who didn't book, turning them into meetings within hours
• Ensure campaigns are tied to clear buying signals and the messaging is sharp enough to strengthen Kick's brand.
• Build and run the outbound stack: domain warming, email and call sequences, lead routing and CRM hygiene, so reps can run signal-led campaigns tailored by account tier, buying signal, and problem hypothesis.
• Build RevOps foundations by driving reporting on what's working and not, with (i.e., show rate and conversion split by cold vs. warm, source, message and rep)
• Get AEs outbound-ready with scripts, objection handling, and a weekly cadence that keeps the numbers visible
• Partner with Growth on outbound plays that generate new MQLs

• Has 4-7 years of experience working on 0→1 outbound as BDR/SDR leader, running an outbound Agency, and consistently surpasses targets.
• Has run cold outbound end to end: built the lists, written the sequences, tested messaging and dialed their way to a repeatable number
• Enjoys the phone and is comfortable spending most of the day dialing and in the inbox
• Incredibly detail-oriented who takes the craft of messaging, scripting, and brand extremely seriously
• Is a hands-on builder who's comfortable without a RevOps or enablement team, and will set up sequences, clean CRM data and build lead (e.g., Clay) tables themselves
• Uses AI to accelerate research, enrichment, prioritization, routing, and first drafts while knowing what to keep human
• Does well at startup intensity: fast feedback, shifting priorities and a number the whole company can see
• Is based in, or willing to relocate to, Toronto (4 days/week in office)

• Sold or prospected into accountants, bookkeepers or accounting firms
• Were one of the first BDRs at a startup and helped write the playbook
• Set up outbound infrastructure yourself: deliverability and domain warming, HubSpot or Apollo sequencing, Clay
• Onboarded or coached other BDRs

• Downtown Toronto, in person, 4-5 days per week

• Top-of-market $175,000-$215,000 CAD total compensation + meaningful equity
• Employee-friendly equity (QSBS eligible, early exercise, extended exercise)
• 100% employer paid medical, dental, and vision benefits (employee + dependents)
• Apple laptop/headset, health/commuter stipends
• Daily lunch and unlimited Verve coffee

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.