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Posted 3 months ago

Open

Head of Revenue

CanadaRemoteFull-time

AI Summary

Own the end-to-end revenue motion for a cloud-based SaaS product, driving outbound sales, pipeline creation, and deal closure into new verticals and geographies.

About this role

The Opportunity

We’ve built a new cloud-based SaaS product that solves a high-value problem in enterprise software lifecycle management—and early traction through our existing portfolio company’s customer base has validated product-market fit.

Now we’re ready to expand.We’re hiring a Head of Revenue to take what’s working and drive it into new verticals, new geographies, and net-new accounts—building a repeatable, scalable revenue motion along the way.

You’ll be backed by permanent capital, built-in distribution through an established customer base in regulated markets (higher ed, public sector, healthcare), and a product with a clear platform expansion path. This role has a direct line to CRO-level ownership as the business grows.

What You’ll Do

Own the 0 → 1 Revenue Motion

  • Own full-cycle sales: prospecting, discovery, demo, proposal, negotiation, close

  • Build pipeline through targeted outbound, events, partnerships, and network leverage

  • Sell into cross-functional buying committees (IT, procurement, finance) in complex organizations

  • Expand into new verticals and geographies beyond our initial beachhead

Be the AI-Native GTM Swiss Army Knife

  • Use AI tools, agents, and automation to drive high-volume outbound at a pace that would normally require a full SDR team

  • Build AI-powered workflows for prospecting, personalization, call prep, and follow-up sequencing

  • Leverage AI to analyze customer conversations, extract buying signals, and surface patterns that inform strategy

  • Treat your GTM stack like a product—always experimenting, always iterating

Build the Playbook

  • Refine ICP, positioning, and talk tracks based on what converts in-market

  • Capture buyer feedback and partner with product/engineering to shape the roadmap

  • Create the sales playbook that enables future hires (SDRs, AEs, partners) as momentum builds

  • Help shape the commercial org and scale plan—this is a leadership trajectory, not just a selling seat

What Success Looks Like

  • First 30 days: Deep product fluency, target account list built, outbound motion live and producing conversations

  • 60–90 days: Qualified pipeline with measurable conversion, early wins in motion, AI workflows accelerating velocity

  • 6–12 months: Predictable revenue engine, multiple reference customers, clear plan for scaling the team

What We’re Looking For

Must-Haves

  • 6–12+ years in B2B SaaS revenue roles with full-cycle closing experience

  • Proven ability to create pipeline and close—you can manufacture demand, not just manage inbound

  • Experience selling into complex orgs with multiple stakeholders and procurement processes

  • Active,demonstrated use of AI tools in your sales workflow—not aspirational, real

  • Builder mindset: high ownership, structured execution, comfort in ambiguity

Nice-to-Haves

  • Experience in higher ed, public sector, healthcare, or other regulated environments

  • Familiarity with ITSM, ITAM, SAM, or procurement/vendor management concepts

  • Experience launching a new product or building a GTM motion from scratch

  • Partner/channel experience (associations, consultants, resellers)

Compensation

Base salary + commission (OTE) tied to revenue outcomes, with a ramp period and milestone-based accelerators aligned to early-stage growth. Remote-friendly with travel for key customer meetings and conferences.

If you sell with conviction, build with AI, and want to own the commercial trajectory of a product with real market pull—we want to hear from you.

#PortfolioLighthouse

Skills

AI AgentsAI ToolsAutomationB2B SaaSClosingDemoDiscoveryFull-cycle SalesITAMITSMNegotiationOutbound SalesProcurementProspectingSAM

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