Ai is building AI purpose-built for finance to help teams do more. We’re already trusted by leading enterprises and developers with over $5T under management with Boosted.
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 contemporary investment professionals will win the future of finance by using the best tools; a unique competitive edge powered by data, experimentation, and automation.
AiWe’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.
Enterprise Sales Executive 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. Identify, prospect, and develop relationships with enterprise financial institutionsDrive end-to-end sales cycles with support from Business Development Reps, Solutions Consultants, and C-Suite along from initial outreach through negotiation, close, and handoffOwn Complex, Multi-Stakeholder Deals Use your expertise to advise senior decision-makers on how to use AI as a competitive advantage in their workflowsNavigate consultative sales cycles with multiple stakeholders and competing prioritiesLead commercial negotiations and partner closely with legal, finance, and leadershipBe a Trusted Advisor to Customers Deeply understand customer workflows, investment processes, and business objectivesClearly articulate Boosted.




Ai’s value and differentiation in the context of financial marketsExceed customer expectations through thoughtful engagement and follow-throughGrow 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 winYour voice matters in partnering with Marketing, Product, and Customer teams to continuously improve your role, the product, and the customer experienceYou 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 togetherWho you are 8+ years of experience in B2B sales, with a strong foundation in business development at a large enterprise organization (e.
AWS, Salesforce, Oracle or similar)8+ years of experience as a quota-carrying Account Executive closing complex dealsExperience managing large deal sizes and navigating multi-stakeholder buying processesProven ability to build pipeline proactively through outbound effortsStrong communication skills — able to earn credibility with senior financial executivesAnalytical mindset with the ability to understand customer needs, mapping to business valueHigh ownership mentality and comfort operating in an evolving, early-stage environmentBonus attributes Experience selling into asset management, wealth management, or broader financial servicesFamiliarity with AI, data platforms,



or workflow automation toolsExperience helping build or refine enterprise GTM motions at a scaling startupWhy Boosted We believe the best sales organizations are built by people who care deeply about their craft, their customers, and their teammates. Own large scale enterprise accounts early in the company’s growthTeam directly with leadership to shape our enterprise sales strategy, valuing your perspectiveSell a sophisticated AI product solving real problems for financial professionalsBuild your career at a company operating at the intersection of fintech and AICompensation The salary range for this full-time position is $250,000-$300,000, which represents the minimum and maximum target salary for new hires in this role. This role is eligible to participate in commission-based compensation under our sales incentive plan. Bonus payments are performance–based and subject to the terms and conditions of the applicable plan. In addition to salary and bonus, employees are eligible to participate in our equity program. Flexible (Unlimited) Paid Time OffMedical, Dental, and Vision benefits for you and your familyLife Insurance and Disability BenefitsAccess to a 401(k) retirement savings plan (for U.
Ai Alfa™ to make moneyWe love the energy of in-person collaboration while also offering the flexibility to work from home when neededBe you, with us To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. #

📌 Finance Sales Representative (Winnipeg)
🏢 Boosted.ai
📍 Winnipeg