Head of Business Development at Jobgether – United States

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Head of Business Development in Canada.

This is a senior commercial leadership role focused on driving growth for AI-driven solutions in a fast-scaling, innovation-led environment. The position blends hands-on execution with long-term strategic design, requiring someone who can actively close complex enterprise deals while simultaneously building the systems, processes, and teams that will scale revenue generation. You will shape go-to-market strategy, define commercial models, and own pipeline performance across services and productized offerings. Acting as both a closer and a builder, you will partner closely with product, delivery, and leadership teams to align market needs with solution development. This role is ideal for a commercially driven leader who thrives in ambiguity, moves quickly, and enjoys creating structure where none yet exists. You will directly influence revenue outcomes, organizational design, and the future direction of AI offerings.

You will lead end-to-end business development strategy and execution for AI solutions, combining immediate revenue generation with long-term commercial system design. Your responsibilities include:

• Defining and executing go-to-market strategy, including target segments, messaging, channels, and repeatable sales motions.
• Driving full-cycle enterprise sales, from lead generation and qualification to negotiation and deal closure, ensuring smooth transition to delivery teams.
• Designing commercial frameworks including pricing, contracts, billing structures, and incentive models to support scalable growth.
• Building and optimizing business development infrastructure such as CRM systems, forecasting models, dashboards, playbooks, and reporting cadences.
• Recruiting, mentoring, and scaling business development talent, including onboarding frameworks, performance metrics, and career development paths.
• Partnering closely with product, design, and delivery teams to align market feedback with product evolution and delivery capability.
• Running structured experiments on GTM strategies and validating new revenue models across services and studio-based offerings.
• Owning revenue performance, pipeline health, and forecasting accuracy while reporting insights to senior leadership.

The ideal candidate brings deep enterprise sales expertise and proven experience building scalable commercial functions from the ground up. You are both a strategic thinker and a hands-on operator, capable of closing deals while designing the systems that enable others to do the same. Key qualifications include:

• 8+ years of experience in B2B enterprise sales, business development, or commercial leadership roles.
• Proven track record of closing complex, multi-stakeholder deals in competitive environments.
• Experience designing commercial models, pricing strategies, and compensation structures.
• Strong ability to build BD infrastructure including CRM workflows, forecasting systems, and sales playbooks.
• Demonstrated success in scaling early-stage or high-growth sales organizations.
• Strong negotiation, communication, and stakeholder management skills across executive-level audiences.
• Ability to collaborate closely with product and delivery teams to align offerings with market needs.
• Comfortable operating in ambiguous, fast-moving environments with a bias toward execution.
• Experience in enterprise, professional services, or hybrid services-and-product models is highly valuable.

• Competitive senior leadership compensation package including base salary, performance bonuses, commissions, and potential equity participation.
• Remote-friendly work arrangement across Canada (with occasional travel for client meetings and team engagements).
• Opportunity to shape and lead the commercial engine of a rapidly scaling AI-focused business.
• High-impact role with direct influence on revenue strategy, product direction, and organizational growth.
• Dynamic, entrepreneurial environment with strong autonomy and ownership.
• Inclusive and collaborative culture focused on innovation, accountability, and meaningful client impact.