Head of Go-To-Market at Fiscal AI in Toronto, Ontario, Canada

Position: Head of Go-To-Market
Salary: $200,000 base salary to $400,000 on-target earnings (OTE)
Location: This role is Toronto-based, with exceptional New York-based candidates also considered.

About Fiscal.ai

Fiscal.ai is a leading research and data platform built for capital markets professionals. Combining a high-performance research Terminal with a modern, near-real-time fundamentals API and MCP server, Fiscal.ai is redefining financial data infrastructure for the AI era. The company serves thousands of institutional and professional Clients while reaching millions of end-users through API Clients.

The Role

Fiscal.ai is hiring a Head of Go-To-Market to lead and scale our revenue engine. Reporting directly to the CEO, you will own sales, marketing, customer success, account management, and partnerships across our two core segments: institutional investors and the fintech companies building on our API and MCP server.

You will be stepping into a strong foundation. Fiscal.ai has a proven product with clear product-market fit, an impressive client list, and significant inbound demand. Sales reps, account management, and BDR functions are already in place with a proven track record, supported by a well-defined process for closing deals. Your mandate is to take the go-to-market organization from founder-led sales to a scalable function that runs under your leadership.

This is a role for a proven sales leader who is ready to step up. You will set the strategy, sharpen the playbook, and stay close to the customer. You will lead from the front by running your own deals, joining reps on key calls, and personally opening doors with high-value accounts. You will have a direct, visible impact on the growth of the company.

This role is based in Toronto. We will consider exceptional candidates based in New York.

Key Responsibilities

• Own the full revenue number across new business, expansion, and retention.
• Lead, coach, and grow the sales team, including hiring, quota setting, territory planning, and compensation design.
• Carry and close a book of strategic accounts across both institutional and fintech segments.
• Build and execute the go-to-market strategy for institutional clients (hedge funds, asset managers, banks, and research teams) and fintech clients (platforms, AI companies, and data products embedding Fiscal.ai through our API and MCP server).
• Own marketing, including positioning, messaging, demand generation, content, and events, and partner with the CEO on brand and product launches.
• Build the customer success and account management function to drive adoption, renewals, and expansion.
• Develop and manage strategic partnerships, including distribution, integration, and channel relationships.
• Establish pipeline discipline, accurate forecasting, and clear reporting to the CEO and board.
• Bring customer insight back to product and engineering to help shape the roadmap.
• Represent Fiscal.ai at industry conferences and events.

• 8+ years of B2B sales experience in capital markets, selling to institutional investors, financial institutions, or fintechs.
• 3+ years managing and developing a sales team as a senior manager, director, or equivalent.
• A track record of consistently exceeding targets, both as an individual contributor and as a team leader.
• Experience in a startup or high-growth environment, including building process and structure where little existed.
• Comfort with complex enterprise sales cycles and multi-stakeholder deals.
• A hands-on approach and willingness to prospect, run demos, negotiate, and close.
• Strong communication skills and a structured, data-driven approach to managing a business.
• Ability to work from our Toronto office, or from New York for exceptional candidates.
• Ability to travel regularly.

Nice to Haves

• Experience selling financial data, research, or analytics products.
• An established network on the buy side, such as hedge funds, asset managers, and family offices.
• Relationships across the fintech ecosystem.
• Experience selling API or usage-based products to technical buyers.
• Prior exposure to leading marketing, customer success, or partnerships.
• Familiarity with how AI tools are changing financial research workflows.

Compensation

• $200,000 base salary
• $400,000 on-target earnings (OTE)
• Equity
• Paid time off
• Benefits