$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.
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
Requirements
- 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)
Benefits
Compensation:
$200,000 base salary ($400,000 CAD+ OTE uncapped) + Equity
Toronto HQ Hybrid (Remote-friendly for top performers)
Standard Employee Benefits
