Director, Sales Retail & E-Commerce (Toronto)

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. 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. Ribbon is on a mission to help every employer find the right people and hire 10× faster. 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. Building a world‑class sales engine is now the defining lever to scale a new category in hiring. 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. 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 data‑driven: forecasting, pipeline math, conversion rates, and experimentation matter to you. Market-competitive salary + meaningful equity. 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. Remote first doesn’t mean remote only. Apply on Kit Job: kitjob.ca/job/2osgrn