Chief of Staff

Kick; Toronto; On-site; CAD 241,000 - 312,000; Full time

Benefits offered by this job

Top-of-market compensation

Equity with QSBS eligibility

100% employer-paid medical, dental, &

Equipment stipend

Daily lunch & Verve coffee

Job summary

Kick is seeking an experienced, high-agency professional to join the leadership team and scale finance, operations, and GTM projects. You will work directly with the CEO and Head of Finance & Operations to drive initiatives that scale the organization 100x, from finance tooling to HR operations and investor relations.

You will build dashboards and workflows, optimize revenue operations and reporting, and lead hiring and vendor decisions.

Qualifications

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

Responsibilities

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

Skills

Financial modeling

Dashboard development

Automation tooling

AI proficiency

Strong writing/communication

Tools

Clay

n8n

Zapier

Claude Code

Job description

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

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

About The Role

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.

What You'll Do

• 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

Ideal Candidate

• 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

Bonus If You Have

• 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.)

Location

• In person Palo Alto, CA (Preferred) with in person in NYC or Toronto for the right candidate

What We Offer

• 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

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.