Head of Revenue in Winnipeg

Professional Computing Resources (PCR) supports complex, regulated organizations, especially higher education and the public sector, with technology asset management solutions across hardware and telecom. Orbit is PCR’s new cloud product for software lifecycle management. Orbit unifies software spend, usage, renewals, vendor contracts, and ROI insights into a single system of record, paired with an AI powered layer that helps teams surface what matters and what to do next.

The role involves leading Orbit’s go to market from launch through early scale. This is the first dedicated commercial hire for Orbit. You will own pipeline creation, run full cycle deals, and build the repeatable sales motion we will scale over time. This is a hands-on operator role, acting as a key bridge between the market and product.

What you’ll do and own:

• Own revenue end to end, hands on
• Own new revenue for Orbit and take a hands on approach to closing business
• Build pipeline through targeted outbound, webinars and events, partnerships, and leveraging PCR’s installed base
• Run deals end to end from discovery to demo to pilot or proof to proposal to negotiation to close
• Sell to cross functional stakeholders and buying committees across IT, procurement, finance, and operations
• Maintain strong CRM hygiene, forecasting, and a consistent weekly operating cadence for pipeline reviews and deal strategy
• Build demand in a scrappy, repeatable way
• Create and run outbound motions including account lists, sequencing, messaging tests, and a call email LinkedIn mix
• Develop campaigns that create spikes in demand such as webinars, customer showcases, partner sessions, and conference follow ups
• Establish a simple measurable funnel and iterate quickly using conversion rates, cycle length, and win loss themes
• Use PCR’s credibility, relationships, and customer access to accelerate trust and shorten cycles
• Translate market feedback into shipped must haves
• Spend meaningful time in customer conversations to understand workflows, blockers, and urgency drivers
• Turn insights into structured inputs for product and engineering including requirements, prioritization, integrations, packaging, and what needs to be true to win and expand
• Partner closely with product and engineering to sharpen workflows and push fast iterations that improve conversion, adoption, and retention
• Create early proof points such as reference customers, case studies, and outcome narratives
• Continuously look for opportunities to expand Orbit into adjacent needs across the higher ed and public sector IT workflow
• Identify and validate new modules, integrations, and next products through discovery
• Bring a GM mindset to growth by increasing ACV, improving retention and expansion, and strengthening Orbit’s strategic position over the next three to five years
• Create the repeatable sales playbook including ICP, messaging, talk tracks, demo narrative, objection handling, sequences, and lightweight enablement
• Recommend when to add capacity such as SDR, marketing support, partners, and CS based on leading indicators and what is proven
• Help define the longer term commercial approach including coverage model, partner strategy, and the operating cadence that scales

Ideal background and requirements:

• 6 to 12 plus years in B2B SaaS revenue roles with full cycle closing experience
• Proven ability to create pipeline, not just work inbound, and deliver against a revenue target
• Experience selling into multi stakeholder, multi budget environments with comfort navigating procurement, legal, and security
• Strong discovery, presentation, negotiation, and written communication skills
• High ownership and operational discipline
• Experience in a startup, early stage, or bootstrapped environment
• Demonstrated ability to work with product and translate customer feedback into must haves
• Experience launching a new product or building a repeatable motion from scratch

Nice to haves:

• Higher ed, public sector, or healthcare experience
• Familiarity with ITSM, ITAM, SAM, procurement, vendor management, or contract lifecycle concepts
• Partnership or channel experience with resellers, associations, consultants, or ISV partners
• AI curiosity and comfort positioning AI enabled workflows credibly with practical value

Compensation: Base salary plus bonus tied to value creation in Orbit, specifically profitable MRR growth.

Location and travel: Remote friendly, with travel for key customer meetings, conferences, and relationship building as needed.