Position: Head of Go-To-Market

Salary:
$200,000 base salary to $400,000 on-target earnings (OTE) 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. 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. 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. 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. 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. 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. ai at industry conferences and events. ~3+ years managing and developing a sales team as a senior manager, director, or equivalent. ~ Experience in a startup or high-growth environment, including building process and structure where little existed. ~ Strong communication skills and a structured, data-driven approach to managing a business. ~ Ability to work from our Toronto office, or from Recent York for exceptional candidates. ~ Ability to travel regularly. Experience selling financial data, research, or analytics products. An established network on the buy side, such as hedge funds, asset managers, and family offices. Experience selling API or usage-based products to technical buyers. Prior exposure to leading marketing, customer success, or partnerships. Equity ~

📌 Temporary Fulltime (Toronto)
🏢 Fiscal.ai
📍 Toronto