Head of Revenue

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take full ownership of revenue from start to finish, taking a hands-on approach.

• Drive new revenue for Orbit by actively closing business opportunities.

• Generate pipeline through targeted outbound strategies, webinars, events, partnerships, and leveraging PCR’s existing customer base.

• Manage deals from initial discovery through to demos, pilots, proposals, negotiations, and closure.

• Engage with cross-functional stakeholders and buying committees across IT, procurement, finance, and operations.

• Ensure robust CRM practices, accurate forecasting, and maintain a consistent weekly rhythm for pipeline reviews and deal strategies.

• Develop and execute outbound strategies including account lists, sequencing, messaging tests, and a mix of calls, emails, and LinkedIn outreach.

• Design campaigns that stimulate demand, such as webinars, customer showcases, partner events, and follow-ups from conferences.

• Create a straightforward and measurable funnel while iterating quickly using conversion rates, cycle lengths, and win/loss themes.

• Leverage PCR’s credibility, relationships, and customer access to build trust and reduce sales cycles.

• Dedicate time to customer discussions to gain insights into workflows, challenges, and urgency factors.

• Convert insights into structured inputs for product and engineering, including requirements, prioritization, integrations, packaging, and essential conditions for success and growth.

• Collaborate closely with product and engineering teams to refine workflows and encourage rapid iterations that enhance conversion, adoption, and retention.

• Develop initial proof points such as reference customers, case studies, and outcome narratives.

• Continuously seek opportunities to extend Orbit's reach into adjacent needs within the higher education and public sector IT workflows served by PCR.

• Identify and validate new modules, integrations, and forthcoming products through discovery, and assist in formulating actionable build and sell plans for the most promising opportunities.

• Adopt a GM mindset towards growth by increasing ACV, enhancing retention and expansion, and fortifying Orbit’s strategic position over the next three to five years.

• Create a repeatable sales playbook that includes ideal customer profiles, messaging, talk tracks, demo narratives, objection handling techniques, sequences, and lightweight enablement materials.

• Advise on the timing for adding capacity, such as SDRs, marketing support, partners, and customer success based on leading indicators and proven strategies.

• Contribute to defining the long-term commercial strategy, including coverage models, partner frameworks, and scalable operating cadences.

⛳️ Requirements

• 6 to 12+ years of experience in B2B SaaS revenue roles with comprehensive closing experience.

• Proven track record of generating pipeline, not just managing inbound leads, and meeting revenue targets.

• Experience selling in multi-stakeholder, multi-budget environments while comfortably navigating procurement, legal, and security processes.

• Excellent skills in discovery, presentation, negotiation, and written communication.

• Strong sense of ownership and operational discipline, effectively managing deals and improving processes.

• Background in a startup, early-stage, or bootstrapped environment where you took on multiple roles and established go-to-market foundations.

• Demonstrated capability to collaborate with product teams, identify product opportunities from customer insights, and translate them into essential features with product and engineering teams.

• Experience in launching a new product or developing a repeatable sales motion from the ground up.

🏝️ Benefits

• Competitive salary and performance-based incentives.

• Opportunities for professional development and career advancement.

• Flexible work environment and work-life balance.

• Health, dental, and vision insurance coverage.

• Generous vacation and paid time off policies.