Chief of Staff (Ontario)

Chief of Staff (Ontario)

01 Oct
|
Kick
|
Ontario

01 Oct

Kick

Ontario

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 quick 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.

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📌 Chief of Staff (Ontario)
🏢 Kick
📍 Ontario

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