Senior Direct Sales Executive, Boosted.ai

• 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)
• 5+ 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

Desirable

• 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