Boosted.ai is building AI purpose-built for finance to help teams do more. Our mission is to optimize investing and boost productivity. We’re already trusted by leading enterprises and developers with over $5T under management with Boosted.ai. From the fastest growing hedge funds to global financial institutions, our tool lets our users stay ahead of the competition with AI that works for them. We believe that modern investment professionals will win the future of finance by using the best tools; a unique competitive edge powered by data, experimentation, and automation. Boosted.ai is the platform they use to cut through data overload, outpace competitors, and reclaim their time. We’re looking for sharp, low-ego people to help teams find their edge.

Why is Boosted.ai the best place to work?

Our product is used every day by investors at the world’s largest financial institutions and most popular investment platforms

We’re scaling quickly. We have ramped roughly 5× over the past year and growth is accelerating

We’ve built a culture people actively want to be part of. Many of our strongest applicants come from firms that already use Boosted.ai

We’re well-capitalized and long-term focused, backed by investors who have helped define modern fintech and enterprise software, including Spark Capital, Ten Coves Capital, Portage Ventures, and RBC.

Boosted.ai is growing fast, and seeking Senior Enterprise Sales Executives to help scale our enterprise go-to-market motion. This is a hybrid role based in our Toronto office, with an expectation of working in person 2‑3 days per week. For the right candidate, this could be a 100% remote role. A highly effective candidate will find themselves on the road 30‑50% of the time.

What You’ll Do
Quarterback Enterprise Deals from Prospect to Close

Identify, prospect,



and develop relationships with enterprise financial institutions

Drive end-to-end sales cycles with support from Business Development Reps, Solutions Consultants, and C‑Suite along from initial outreach through negotiation, close, and handoff

Own Complex, Multi‑Stakeholder Deals

Use your expertise to advise senior decision makers on how to use AI as a competitive advantage in their workflows

Navigate consultative sales cycles with multiple stakeholders and competing priorities

Lead commercial negotiations and partner closely with legal, finance, and leadership

Be a Trusted Advisor to Customers

Deeply understand customer workflows, investment processes, and business objectives

Clearly articulate Boosted.ai’s value and differentiation in the context of financial markets

Exceed customer expectations through thoughtful engagement and follow-through

Grow the Enterprise Sales Motion

You will be an early member of our enterprise sales team in a dynamically changing AI landscape, with the best tools in class to help you shape how we win

Your voice matters in partnering with Marketing, Product, and Customer teams to continuously improve your role, the product, and the customer experience

You will be supported by BDRs, Forward Led Engineers, and Executive Leadership to win and expand enterprise accounts – we truly work as a team to win together

Who you are

10+ years of experience in B2B sales,



with a solid foundation in business development at a large enterprise organization (e.g., AWS, Salesforce, Oracle or similar)

10+ years of experience as a quota‑carrying Account Executive closing complex deals

Experience managing large deal sizes and navigating multi‑stakeholder buying processes

Proven ability to build pipeline proactively through outbound efforts

Strong communication skills — able to earn credibility with senior financial executives

Analytical mindset with the ability to understand customer needs, mapping to business value

High ownership mentality and comfort operating in an evolving, early‑stage environment

Bonus attributes

Experience selling into asset management, wealth management, or broader financial services

Familiarity with AI, data platforms, or workflow automation tools

Experience helping build or refine enterprise GTM motions at a scaling startup

Why Boosted
About We believe the best sales organizations are built by people who care deeply about their craft, their customers, and their teammates. At Boosted.ai, you’ll have the opportunity to:

Own large scale enterprise accounts early in the company’s growth

Team directly with leadership to shape our enterprise sales strategy, valuing your perspective

Sell a sophisticated AI product solving real problems for financial professionals

Build your career at a company operating at the intersection of fintech and AI

Compensation
At Boosted.ai, we believe in fair and transparent compensation practices. The salary range for this full‑time position is $300,000–$350,000, which represents the minimum and maximum target salary for new hires in this role. Actual salary will be determined based on factors such as

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📌 Senior Enterprise Sales Executive (Ontario)
🏢 Boosted.ai
📍 Ontario