Hybrid Head of Sales

Posted last week

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About the role

  • Head of Sales for Ribbon driving B2B SaaS growth by transforming their sales process. Managing entire sales motion from strategy to execution with a focus on scaling revenue.

Responsibilities

  • 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.

Requirements

  • 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.

Benefits

  • Competitive salary + meaningful equity.
  • Cutting-edge tech.
  • Health & wellness stipend.
  • Annual international offsite.
  • Regular team lunches & meetups in Toronto.

Job title

Head of Sales

Job type

Experience level

Lead

Salary

Not specified

Degree requirement

Bachelor's Degree

Location requirements

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