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Open nowPosted 192 days ago

Head of Revenue

Workable (global search)108,016 open roles

Where
Canada
Work mode
Remote
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Your applicationOpen nowHead of RevenueWorkable (global search) · Canada

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The clock on this job

Early applications get read.

7.9% of postings close within 7 days. Measured by our own scanner across the market. Workable (global search) postings stay open a median of 7 days.

Share of postings closed within
  1. 1.6%1 day
  2. 3.6%3 days
  3. 7.9%7 days
  4. 14.9%14 days
  5. 34.0%30 days
This job: posted 192 days ago

Workable (global search) median: 7 days open

The posting

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

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