Chief of Staff

RiseMe; Toronto; On-site; CAD 240,000 - 311,000; Full time

Benefits offered by this job

Medical, dental, vision coverage

Equity (QSBS eligible)

Equipment provided

Meals and coffee

Stipends

Job summary

RiseMe is seeking a high-agency problem solver to scale finance, operations and GTM projects. You will work directly with our CEO and Head of Finance & Operations to drive initiatives to completion so they scale 100X.

This project-based role spans building dashboards, automations, and processes, supporting fundraising, RevOps, HR, and AI-driven improvements. In-person opportunities exist in Palo Alto, NYC, or Toronto for the right candidate.

Qualifications

• 3–7 years post-grad with experience in MBB, investment banking, or chief of staff.
• Strong financial acumen: model building and understanding ARR, NRR, gross margin, rev rec.
• Hands-on builder who ships dashboards, automations, and processes.
• AI-native: daily use of Claude/ChatGPT and workflows with Clay, n8n, Zapier or Claude Code.
• High agency: manages multiple projects with initiative.
• Clear writer and communicator, credible with CEO, investors and candidates.

Responsibilities

• Lead finance, operations and GTM projects with high ownership.
• Optimize finance tech stack and billing processes for autonomy.
• Drive live ARR tracking, margin analyses and projections.
• Support fundraising, data room prep and investor updates.
• Build RevOps foundations: document sales processes, CRM setup, funnel reporting.
• Improve customer support workflows and implement AI-powered automations.
• Oversee HR ops tech stack and performance management framework.
• Lead key hires from sourcing to close and design work trials.

Skills

Financial modeling

Dashboard building

Automation workflows

AI tools usage

Project ownership

Clear communication

Tools

Clay

n8n

Zapier

Claude Code

Job description

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

This role will primarily be project based, deployed to the most critical projects in the company. Examples include:

• 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.