Direct Sales Executive Jobs in Toronto, ON, Canada
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Toronto, ON, Canada
Senior Direct Sales Executive
Toronto, ON, Canada
$200,000 - $250,000/yearly
Senior Level
Full-Time
Top Benefits
Comprehensive health benefits
Flexible hours and time off
Work from anywhere
About the role
- Boosted.ai is growing fast, and seeking Senior Direct 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
- 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
Benefits
- Comprehensive health benefits
- Flexible hours and time off
- Have fun & learn together
- Work from anywhere
- Opportunity to lead, learn & grow- Experience managing large deal sizes and navigating multi-stakeholder buying processes
- 5+ years of experience as a quota-carrying Account Executive closing complex deals
- Strong communication skills — able to earn credibility with senior financial executives
- Proven ability to build pipeline proactively through outbound efforts
- 5-8 years of experience in B2B sales, with a strong foundation in business development at a large enterprise organization (e.g., AWS, Salesforce, Oracle or similar)
- High ownership mentality and comfort operating in an evolving, early-stage environment
- Analytical mindset with the ability to understand customer needs, mapping to business value
- 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
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About Boosted.ai
Financial Services
51-200
Boosted.ai is how investment managers work smarter. Generative AI built specifically for capital markets provides analytics across millions of data points, through a macroeconomic, microeconomic and portfolio construction lens, giving asset managers the actionable insights they need.
Twitter @BoostedAI