[Hiring] Strategy Principal @Walnut Insurance

Role Description

You'll be the operating and strategy partner to our COO and CPO. Half the job is the work a top strategy consultant does for a client:

• Help decision-making
• Size the opportunity
• Build the case
• Pressure-test the plan
• Write the recommendation

The other half is what a good chief of staff does:

• Turn decisions into execution
• Ensure momentum never depends on two people's calendars

You'll work across sales, product, and partnerships as we grow in Canada and the US, in a regulated industry where banks, telcos, lenders, and insurers are the buyers. You'll do it with an AI-native toolkit that lets one person deliver what used to take a team.

Qualifications

• Five to ten years in strategy consulting, a bank or insurer's strategy or corporate development team, fintech or insurtech operations, venture capital or a founder's office.
• Time at a top-tier consultancy or in an enterprise financial services strategy role.
• Financial services fluency: how banks, lenders, telcos, and carriers buy, what a regulated enterprise sales cycle looks like, and the economics of an insurance program.
• Structured decision-making: comfortable laying out options, making recommendations, and addressing mistakes quickly.
• Expert-level AI building, tested directly in our hiring process.
• A technical background, such as engineering, computer science, or data, and comfort with APIs, SQL, or scripting.
• Commercial instinct from work close to B2B enterprise revenue.
• Strong financial modeling and HubSpot skills.
• Exceptional written communication and time management across two executives and high-stakes work.

Requirements

• Run strategy the way a consultant would.
• Make decisions within agreed guardrails and frame others for the COO and CPO.
• Own follow-through and maintain a current view of obligations across partners, carriers, and the team.
• Shape important deals alongside the Sales Team.
• Build executive materials from notes, data, and direction.
• Maintain accurate records of decisions and partner information.
• Design and run AI workflows that reduce manual work.

Benefits

• A salary of CAD $120,000–$160,000, based on background, skills, and experience, plus equity and benefits.
• Fully remote in Canada, with occasional travel.
• Direct collaboration with the COO and CPO at a scaling fintech.

Your first 90 days

• By day 30, embedded with the COO and CPO, familiar with top deals in Canada and the US, and have run the weekly strategic review twice.
• By day 60, delivered one strategy recommendation acted on by executives, and your first agents are saving the executive team hours each week.
• By day 90, follow-through and reporting run independently, and you own the business case for one priority enterprise deal.

How to apply

Send us three things:

• Your resume and link to your LinkedIn profile.
• A cover letter detailing your experience at a chief of staff or strategy level in financial services.
• Something you built with AI, along with a brief description of the problem it solved and its impact.

Applications without a build sample won't be considered. Our process includes a walkthrough of your build, a live build session, a case on a real Walnut strategy decision, and a paid work sample.