Head of Sales

$200,000 base salary ($400,000 CAD+ OTE uncapped) + EquityToronto HQ (3 days per week in office) (Remote-friendly for top performers) About Fiscal.ai Fiscal.ai is a leading research and data platform for capital markets. Combining a powerful research Terminal with modern APIs, Fiscal.ai is building the modern financial data company. The firm has raised $13M USD in venture backing and is headquartered in Toronto, Canada. With thousands of customers and millions of end-users through their API offerings, Fiscal.ai is building the premiere financial data company in the AI era. Why should you be part of Fiscal.ai's growth story? Shape the future of AI in finance: You’ll sell a product that customers describe as faster, smarter, and more cost-effective than anything else in the market. Join a supportive, high-performing team: We prioritize collaboration, inclusivity, and outcomes—no red tape, just impact. Make your mark: With only 30 team members, every hire plays a critical role. You’ll influence revenue, product feedback, and go-to-market strategy. Work directly with leadership: No bureaucracy—just close access to the founding team. Flexibility and growth: We’re remote-friendly and focused on outcomes. You'll have opportunities to grow into leadership or strategic roles. Mission with momentum: With strong traction and a growing customer base, this is a chance to ride the wave early. The Role We’re looking for a Head of Sales to build and lead our go-to-market organization from the ground up. This person will own the full revenue motion — from refining our sales process and pricing strategy to hiring, coaching, and scaling a high-performing team. You’ll also remain hands-on with key deals, helping close strategic accounts while setting the tone for a data-driven, high-velocity sales culture. This is a rare opportunity to join an early-stage company with strong product-market fit and build the sales engine that powers its next stage of growth. You will be the key leader to bring us from $5M to $20M ARR and beyond. Responsibilities Own the entire sales function, including pipeline generation, forecasting, deal management, and revenue targets Develop and refine the sales playbook, ensuring scalable, repeatable processes for both inbound and outbound motions Hire, coach, and manage a team of Account Executives and SDRs to consistently exceed quota Partner closely with the CEO and Marketing team to define messaging, target accounts, and campaign strategy Manage and forecast pipeline with precision, ensuring accurate revenue visibility and accountability Lead by example with direct involvement in strategic and enterprise-level opportunities Build and maintain strong relationships with key customers and partners Collaborate with Product and Customer Success to ensure a seamless post-sale experience and identify expansion opportunities 8+ years of sales experience, with at least 3 years in a sales leadership role (Head of Sales, Director, or VP) Proven track record of building and scaling B2B SaaS sales teams from early stage to growth Demonstrated ability to meet or exceed multi-million ARR targets Deep understanding of sales operations, including forecasting, metrics, and pipeline management Excellent leadership and coaching skills with the ability to recruit and develop top performers Strong analytical mindset and comfort using data to drive performance Exceptional communication and executive presence — able to represent Fiscal.ai with professionalism and credibility Nice to Haves Experience selling to financial institutions, investment firms, or data-heavy enterprises Previous success at a high-growth SaaS startup (Seed–Series B stage) Compensation: $200,000 base salary ($400,000 CAD+ OTE uncapped) + Equity Toronto HQ Hybrid (Remote-friendly for top performers) Standard Employee Benefits #J-18808-Ljbffr