Strategy Principal, Office of the COO

Chief of Staff-level role | Walnut Insurance | Remote, Canada | Partner to the COO and CPO

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, 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 that decision into execution, so 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. And you'll do it with an AI-native toolkit that lets one person deliver what used to take a team.

Walnut is Canada's leading embedded insurance platform. Partners like Wealthsimple, BMO, KOHO and TELUS use us to launch insurance inside their products in 90 days, compared with nine months or more going direct to a carrier. We hold the carrier relationships, the licences and the compliance; our partners keep the customer.

You've done strategy work to a top-tier standard, in financial services. Maybe that was at a leading consultancy, in a bank or insurer's strategy or corporate development group, at a fintech or insurtech, or in a founder's office doing the same job without the title. You know how a bank, a carrier and an enterprise buyer make decisions, and how long they take. You can read a partner's P&L, a loss ratio and a take rate and tell us whether a program will make money. And you can write a board-grade recommendation on one page.

AI is how you already work, not a tool you'll pick up here. You build agents, Claude Skills and automated workflows as a daily habit, connect them to live systems like HubSpot, Slack and email through APIs and MCP, and can show us what you've built and the impact it had. If you use AI only for drafting and summarizing, this isn't the role.

• Run strategy the way a consultant would. Own the thinking behind our biggest calls: which markets and channels come first, how we price a program, which partners we chase and which we pass on, what a carrier deal is worth. Size markets from the bottom up, model partner economics, map the competition, and bring the COO and CPO options with a recommendation, the trade-offs and the point at which you'd change your mind. You'll run the weekly strategic review that keeps every initiative red, yellow or green.

• Make the call, or frame it. Decide what's yours to decide inside agreed guardrails, and bring the rest to the COO and CPO framed so the decision takes ten minutes. Brief them before key meetings, send recaps with decisions, owners and dates, and hand work off to named owners with clear scope.

• Own follow-through. Keep one current view of what's owed to and by the COO and CPO across partners, carriers and the team. Raise risks before they slip and push deals and projects forward between meetings.

• Shape the deals that matter. Work alongside our Sales Team on pipeline, HubSpot reporting and sales infrastructure. Build the business cases, solution outlines and proposals for enterprise deals with banks, telcos and lenders, and help us build the go-to-market in both markets.

• Build the materials. Turn notes, data and rough direction into executive, investor, partner and board decks, briefs and models, with accurate numbers and a clear point of view. You'll prepare board materials but won't attend board meetings.

• Keep one version of the facts. Maintain the roadmap, requirements and partner records, and make sure material decisions are captured in writing.

• Build our AI operating system. Design and run the Claude Skills, agents and workflows that remove manual work across the executive team. Our stack: Claude (Skills, Code, Cowork, Design, MCP), Granola, HubSpot, Apollo.io, Slack, Google Workspace, Microsoft 365, Figma, Lovable, Lucid, Shortcut and Xero…++…

• 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 is what we're after.

• 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 (premium, loss ratio, commission, take rate). Embedded or creditor insurance experience is a real plus, not a must.

• Structured decision-making: you lay out the options, put numbers on them, make a recommendation and say what would change your mind. You're comfortable being wrong in writing and fixing it fast.

• 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. US market exposure is an asset.

• Strong financial modeling and HubSpot skills.

• Exceptional written communication and time management across two executives and a lot of high-stakes work at once.

By day 30, you're embedded with the COO and CPO, know our top deals in Canada and the US, and have run the weekly strategic review twice. By day 60, you've delivered one strategy recommendation the executives acted on, and your first agents are saving the executive team hours each week. By day 90, follow-through and reporting run without hand-holding, and you own the business case for one priority enterprise deal.

Send us three things:

1. Your resume and link to your LinkedIn profile.

2. A cover letter that shows how you've operated at a chief of staff or strategy level in financial services. Tell us about an executive you partnered with, a high-stakes decision you shaped, and what you delivered, with real outcomes.

3. Something you built with AI, such as an agent, a Skill, an automation, a model or a deck, along with two sentences on the problem it solved and the impact it had. A Loom, a link or a live demo all work.

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.

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. You'll work directly with the COO and CPO at a scaling fintech.