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Head of Sales

2 days ago

Toronto, Ontario, Canada Ribbon AI Full time

Build a world-class revenue engine for a category-defining company.

As Ribbon's first Head of Sales, you'll transform our foundation into a scalable, world-class revenue organization. You'll own the entire sales motion from strategy, pipeline, deals, and execution with ownership to shape how we grow. This is a hands-on leadership role for someone who thrives in complexity, loves closing meaningful deals, and wants to define how modern sales teams operate in the age of AI.

If you've been waiting for the right moment to bring everything you've learned from scaling SaaS into a role with real influence, this is it. You'll work directly with founders and enterprise customers to define not just Ribbon's go-to-market engine, but an entirely new category in hiring.

About Ribbon

Ribbon is on a mission to help every employer find the right people and hire 10× faster. Our always-on voice AI interviewers screen candidates in minutes, surface top talent automatically, and unlock speed and signal that traditional recruiting can't match and freeing recruiters to focus on what actually matters.

We work with high-volume employers, staffing firms, and enterprise teams from SMBs to Fortune 500 brands by helping them slash time-to-hire, reduce recruiter workload, and dramatically improve candidate experience, all without adding headcount.

Backed by world-class investors and already trusted by recognizable brands, Ribbon is entering its next phase of growth. Building a world-class sales engine is now the defining lever to scale a new category in hiring.

How you'll make an impact

  • Own Ribbon's entire sales motion from first call to close to expansion.

  • Design and execute our GTM strategy across SMB, Mid-Market, Enterprise, and Partnerships.

  • Personally close early deals while building a repeatable, scalable sales process.

  • Define ICPs, segmentation, pricing, packaging, and deal structures.

  • Build, hire, coach, and lead our sales org (BDRs, AEs, and Partnerships).

  • Build forecasting models, maintain pipeline hygiene, enforce CRM discipline, and create KPI dashboards.

  • Partner tightly with founders, product, marketing, and CS to align roadmap to revenue.

  • Lead complex sales cycles involving multiple stakeholders, pilots, procurement, and security.

  • Translate customer pain into clear ROI narratives around speed, cost savings, and quality of hire.

  • Continuously test and iterate: messaging, demos, offers, pilots, and close tactics.

  • Represent Ribbon confidently with executives, partners, and at industry events.

We are looking for someone who

  • Has 5–7+ years of B2B SaaS sales experience leading teams.

  • Has built or scaled a sales function at an early-stage startup (Seed–Series B preferred).

  • Is deeply comfortable selling and leading at the same time.

  • Has closed complex deals with HR, Talent, Ops, or adjacent enterprise buyers.

  • Thinks strategically but executes relentlessly ("no hands-off leaders/operator").

  • Is data-driven: forecasting, pipeline math, conversion rates, and experimentation matter to you.

  • Communicates clearly, directly, and with conviction both internally and externally.

  • Thrives in ambiguity, moves fast, and takes full ownership of outcomes.

  • Is excited by AI, the future of work, and re-imagining how hiring actually gets done.

Why Ribbon

  • Competitive salary + meaningful equity. We want you thinking like an owner because you are one.

  • Cutting-edge tech. Build with the latest AI tooling, not yesterday's stack.

  • Health & wellness stipend. Your mind and body are part of the product.

  • Annual international offsite. Each year, we take our team on an exciting journey to a different international destination. It's more than just travel, it's an investment in alignment and collaboration.

  • Regular team lunches & meetups in Toronto. Remote first doesn't mean remote only.

Ready to Standout? How to Apply:

We've ditched the cover letter and initial screening. Experience Ribbon's product by starting your AI interview now - 24/7, no recruiter bottlenecks.

Apply in Seconds: Click here to start your AI Interview - here

Showcase Your True Potential: Go beyond your resume and let your skills shine

Stay Tuned: If you're a match, our team will reach out fast for next steps.

We can't wait to see how you'll write Ribbon into every hiring story.