Head of Business Development

This is a fully remote position, open to applicants in Canada, +1 more country.

📋 Description

• Lead the go-to-market (GTM) and pipeline strategy for AI solutions, encompassing target segments, messaging, channels, and repeatable sales plays.

• Take ownership of direct sales for services and productized solutions: generate leads, qualify opportunities, close deals, and ensure smooth transitions to delivery.

• Develop commercial and billing models, which include pricing, commission structures, contracts, and terms.

• Establish business development (BD) systems and operations, covering CRM hygiene, funnel definitions, forecasting, playbooks, compensation plans, dashboards, and service-level agreements (SLAs).

• Recruit and cultivate BD talent, including sellers and account leads, along with ramp plans, performance metrics, training, and career pathways.

• Collaborate with product, design, and delivery teams to transform customer insights into product enhancements and synchronize commercial strategies with product-market fit.

• Conduct GTM experiments and commercial diligence, validate revenue models for studio investments, and iterate based on market feedback.

• Establish revenue targets, oversee forecasts, and communicate performance to senior leadership.

• Deliver a comprehensive GTM plan, standardized commercial model, predictable pipeline, initial BD hires, initial commercial successes, and a dashboard that links BD activities to revenue and unit economics.

• Report directly to the Partners and collaborate closely with the Founder and Managing Director of AI Solutions.

⛳️ Requirements

• A minimum of 8 years in enterprise B2B sales or business development leadership, with experience in selling services and complex solutions.

• A proven track record of building pipelines and closing deals within multi-stakeholder buying processes.

• Experience in designing commercial models, commission structures, and billing frameworks.

• Demonstrated capability in establishing BD systems, including CRM, playbooks, compensation, and dashboards.

• Excellent negotiation skills and experience in structuring innovative commercial agreements.

• Ability to collaborate with product and delivery teams to align GTM strategies with product-market fit.

• Preference for experience selling into complex buyer ecosystems (enterprise, multi-site operators, or similar).

• Prior experience in a venture studio, incubator, or professional services model that integrates services and equity is preferred.

• Experience in hiring and scaling early-stage sales teams is preferred.

• A tactical closer capable of devising scalable strategies.

• Comfortable with intensive early execution and rapid iteration while developing systems to minimize long-term grind.

• High tolerance for ambiguity and a strong inclination towards action.

• Possess strong judgment, humility, and collaborative leadership skills.

• Commercially rigorous and data-driven.

🏝️ Benefits

• Competitive base salary, performance bonuses, commission, and equity participation.

• Remote-friendly work arrangement within the U.S. / Canada.

• Occasional travel for client meetings, portfolio company engagements, and offsite events.