Chief of Staff

Kick • Toronto, ON

5d • $170,000 - $220,000 • Onsite

About The Position

Kick is growing fast and is planning to soon raise capital to rapidly scale the organization. Our most important problems are cross functional and we need a high-agency problem solver to help us scale. You'll work directly with our CEO and Head of Finance & Operations to drive finance, operations and GTM projects to completion with high ownership so they scale to 100X without you.

Requirements

• 3–7 years post-grad, with experience in MBB, investment banking, or a former chief of staff role.
• Strong financial acumen building models from scratch and understands how ARR, NRR, gross margin and rev rec connect
• Hands-on builder who ships working dashboards, automations and processes on their own
• AI-native: uses Claude or ChatGPT daily and has built workflows with tools like Clay, n8n, Zapier or Claude Code
• High agency: runs several projects at once and makes progress without a playbook
• Clear writer and communicator, credible with the CEO, investors and candidates

Nice To Haves

• Worked in venture, growth equity or been an operator at a high-growth startup (Seed to Series B)
• Experience starting new businesses and/or ventures
• Is highly proficient in using AI tools (e.g., Claude, etc.)

Responsibilities

• Optimize our finance tech stack to operate near autonomously (e.g., upgrade billing process, optimize vendor evaluation & payment processes)
• Drive key reporting efforts (e.g., improved live ARR tracking, margin analyses, projections, etc.)
• Support fundraising and investor relations, from the model and data room to investor updates
• Build our RevOps foundation: document the sales process and CRM setup, own funnel reporting, and find what drives conversion as outbound scales
• Optimize our customer support workflows, improving our agents to deliver best-in-class service
• Build AI agents and automations that give the team leverage, like surfacing buying signals from LinkedIn and X
• Run key hires from sourcing to close, including designing work trials
• Upgrade HR operations, from the tech stack to our first performance management framework
• Jump on whatever matters most next, with direct visibility into CEO priorities

Benefits

• Top-of-market $170,000-$220,000 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed