Senior Direct Sales Executive

JobsCloseBy Editorial Insights

Boosted.ai is seeking a Senior Direct Sales Executive to scale our enterprise go to market from Toronto with a hybrid schedule, including 2 to 3 days in the office and roughly 30 to 50 percent travel. You will quarterback complex multi stakeholder deals from prospecting to close, with BDRs, Solutions Consultants, and executive leadership backing you. The ideal candidate has 5 to 8 years in B2B sales at a large enterprise, 5+ years as a quota carrying AE, and a proven ability to map AI value to financial workflows. Compensation is $200k to $250k base plus commission and equity, plus strong benefits. Tips: tailor your resume to enterprise fintech, quantify wins, show ownership and collaboration, and highlight how you have navigated evolving AI GTM motions.

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 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. 

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

• 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

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

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 $200,000-$250,000, which represents the minimum and maximum target salary for new hires in this role. Actual salary will be determined based on factors such as experience, skills, and location. 

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. During the hiring process, we can provide more specific compensation details applicable to your location.

Our Values

We are guided by a set of values that are at the core of our actions and define our culture. These principles are the foundation of our work, and we are committed to upholding them in everything we do.

• Collaborative – We value our team and know that success can only come from working together
• Client Centric – Our focus is always on our clients and consistently delivering them value
• Action Oriented – We remove barriers and we seek to improve in measurable ways
• Accountable – We are accountable for ourselves, and we hold each other accountable
• Respectful – We are proud of our work, we are respectful of each other’s opinions, and we keep a positive attitude

What we offer

We want our benefits to reflect our values and offer the following to full-time employees:

• Flexible (Unlimited) Paid Time Off
• Medical, Dental, and Vision benefits for you and your family
• Life Insurance and Disability Benefits
• Access to a 401(k) retirement savings plan (for U.S. employees)
• Paid Parental Leave
• Free access to use Boosted.ai Alfa™ to make money
• We love the energy of in-person collaboration while also offering the flexibility to work from home when needed

These benefits are further detailed in Boosted.ai’s policies and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Boosted.ai’s equity plans subject to the terms of the applicable plans and policies.

Be you, with us

We're working to bring the transformative power of AI to every organization in the world. 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 encourage you to apply even if your experience doesn't precisely match the job description. 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.