Head of Business Development

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

📋 Description

• Lead the go-to-market strategy and pipeline development for AI solutions, encompassing target segments, messaging, channels, and repeatable sales tactics.

• Take ownership of direct sales for services and productized solutions, overseeing the process from lead sourcing and qualification to closing and delivery handoff.

• Design commercial and billing frameworks, including pricing, commission structures, contracts, and terms.

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

• Recruit and nurture business development talent, including hiring sales representatives and account leaders, defining ramp-up plans and performance metrics, and creating training and career development paths.

• Collaborate with product, design, and delivery teams to convert customer insights into product enhancements and ensure alignment of commercial strategies with product-market fit.

• Conduct go-to-market experiments and commercial due diligence, validate revenue models for studio investments, and adapt strategies based on market feedback.

• Establish revenue objectives, oversee forecasting, and report performance metrics to senior leadership.

• Deliver a comprehensive go-to-market plan, standardized commercial model, predictable pipeline, business development operating rhythm, initial business development hires along with a hiring and compensation strategy, early commercial successes, and a dashboard linking business development activities to revenue and unit economics.

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

⛳️ Requirements

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

• Proven track record of building a sales pipeline and successfully closing deals within multi-stakeholder buying environments.

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

• Demonstrated capability in establishing business development systems: CRM, playbooks, compensation plans, and dashboards.

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

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

• Preferred: Experience in selling to complex buyer ecosystems (enterprise, multi-site operators, or similar).

• Preferred: Background in a venture studio, incubator, or professional services model that integrates services and equity.

• Preferred: Previous experience in hiring and scaling early-stage sales teams.

• Tactical closer adept at designing scalable strategies.

• Comfortable with intensive early execution and rapid iterations while establishing systems to minimize long-term challenges.

• High tolerance for ambiguity and a proactive approach.

• Strong judgment, humility, and collaborative leadership skills.

• Commercially rigorous and data-driven mindset.

🏝️ Benefits

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

• Flexible remote work arrangement.

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