Walnut is a leading embedded insurance platform helping lenders, fintechs, and digital platforms seamlessly integrate insurance products into their customer journeys. Backed by top investors and trusted by partners like BMO, TELUS, and Wealthsimple, Walnut is building the infrastructure powering the future of insurance.
We're hiring a Head of Sales, US to lead and build Walnut's commercial presence in the United States. This is a true founding role, owning US revenue, sourcing and closing strategic partners, and laying the foundation for a scalable sales organization. The role combines hands-on deal execution with long-term team building and market ownership.
This is a fully remote role for candidates based in the United States, with travel required for partner meetings and industry events.
About Walnut.
Walnut is a leading embedded insurance platform helping financial institutions and fintechs seamlessly integrate insurance products into their customer journeys.
We partner with lenders, banks, and digital platforms to offer protection products, such as income and loan protection, directly within their existing flows. Our platform powers the full lifecycle, including onboarding, policy management, reporting, and insurer connectivity.
Backed by leading investors and trusted by partners like BMO, National Bank, TELUS, and Wealthsimple, Walnut is now expanding aggressively into the United States, our most important growth market.
The opportunity.
Walnut is hiring a Head of Sales, US to lead and build our commercial presence in the United States from the ground up.
This is a true founding sales leader role. You will be our first official US hire, responsible for driving revenue, building our pipeline, closing strategic partners, and ultimately scaling a US-based sales organization.
You will operate as both a player and a coach: owning deals end-to-end while defining the go-to-market strategy, shaping our positioning in the US, and building the foundation for a high-performing team.
This role is ideal for someone who thrives in zero-to-one environments, is highly commercial, and wants to take full ownership of a region with meaningful upside tied directly to growth.
What you'll own.
Build & Execute US Go-To-Market
- Define and execute Walnut's US go-to-market strategy across lenders, financial institutions, fintechs, and platforms
- Identify priority segments, verticals, and partner profiles to drive early traction
- Establish Walnut's brand and credibility in the US embedded insurance and fintech ecosystem
- Act as the voice of the US market internally, influencing product, positioning, and strategy
Own Pipeline, Deals & Revenue
- Build and manage a multi-million-dollar pipeline from scratch in a greenfield market
- Source, qualify, and close new strategic partners
- Own the full sales cycle: discovery, solutioning, commercial structuring, negotiation, and close
- Sell complex, multi-stakeholder deals involving technology, financial products, and compliance
- Expand revenue within existing US partners (new products, channels, and adoption)
- Own forecasting and maintain a disciplined, data-driven pipeline
Sell a Complex, High-Value Product
- Sell Walnut's embedded insurance platform into lenders and financial institutions
- Navigate deals that involve multiple stakeholders (distribution partners, carriers, legal/compliance, product teams)
- Structure partnerships that combine SaaS fees with variable / transactional revenue components
- Act as a trusted advisor to executive stakeholders
Build the US Sales Function
- Serve as the founding sales leader for the US region
- Design scalable sales processes, qualification frameworks, and playbooks
- Hire, onboard, and lead future US-based sales and account management team members
- Help define the long-term org structure across the US and Canada
Operate as a Strategic Partner Internally
- Collaborate closely with Product, Engineering, Implementation, Legal, and Compliance
- Bring structured market feedback to influence roadmap and product development
- Partner with leadership on pricing, packaging, and expansion strategy
How you'll work.
- Fully remote, US-based, with regular travel for partner meetings and industry events
- High-autonomy, high-accountability environment with direct access to leadership
- Hands-on execution combined with strategic ownership
- Expected to leverage modern sales tooling and AI to drive pipeline generation, research, and efficiency
What we're looking for.
Core Experience
- 8+ years in B2B sales, partnerships, or business development
- Proven success building and scaling a new territory, region, or market from zero
- Strong experience selling into lenders, financial institutions, or fintech companies
- Background in SaaS, fintech, lending infrastructure, or embedded finance
- Track record of closing complex, high-value, multi-stakeholder deals
- Experience owning multi-million-dollar revenue targets
- Prior experience hiring or leading sales teams
Key Strengths
- Highly commercial and ownership-driven; thinks like a GM of the region
- Strong outbound and pipeline generation capabilities (not reliant on inbound)
- Comfortable operating in ambiguity and building structure from scratch
- Executive presence with strong communication and negotiation skills
- Data-driven and disciplined in forecasting and pipeline management
- Advanced user of modern sales tools and AI-driven workflows to increase productivity
Nice to Have
- Experience with embedded insurance or insurance-enabled products
- Existing network within US lending, fintech, or financial services ecosystem
- Experience working in startup or early-stage environments
- Exposure to US insurance carriers and distribution models
- Experience working with distributed or international teams
Why join Walnut.
- Own and build Walnut's most important growth market
- Be the founding US sales leader with real autonomy and influence
- Work at the intersection of fintech, insurance, and infrastructure
- Direct impact on company strategy and revenue growth
- Competitive compensation with meaningful upside tied to performance and equity
Ready to apply?
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