Head of Sales

$200,000 base salary ($400,000 CAD+ OTE uncapped) + Equity
Toronto 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.
  

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.

• 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

• 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