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About the Role

Own the enterprise sales journey from first conversation through close. Work directly with Talent, HR, Operations, and business leaders to help them understand how AI can transform the way they hire. Build pipeline, run consultative sales cycles, understand customer hiring challenges, and close high-impact enterprise opportunities. This is a hands-on role for someone who thrives in fast-moving environments, can sell strategically, and wants to help define the category for AI-powered recruiting.

Responsibilities

Own the full enterprise sales cycle, from prospecting and discovery through evaluation, negotiation, and close.
Build strong relationships with Talent, HR, Operations, and executive stakeholders to understand their hiring priorities, workflows, and business goals.
Run compelling discovery calls, product demos, pilot discussions, business cases, and executive-level presentations.
Partner closely with Customer Success, Product, Engineering, and Leadership to structure pilots, proposals, pricing, and implementation plans that drive customer success.
Develop strategic account plans, manage complex deal cycles, and consistently drive pipeline creation, deal progression, and revenue growth.

Requirements

Has 4+ years of B2B SaaS sales experience, ideally selling into enterprise, mid-market, HR, Talent Acquisition, recruiting, staffing, or workforce-related buyers.
Has experience owning full-cycle sales, including outbound prospecting, discovery, demos, business case development, negotiation, and closing.
Can sell consultatively to multiple stakeholders and uncover business pain around hiring speed, recruiter capacity, candidate quality, operational efficiency, and cost.
Is comfortable running complex sales cycles with senior leaders, including Heads of Talent, CHROs, HR leaders, Operations leaders, and executives.
Has strong commercial judgment and can manage forecasting, pipeline hygiene, next steps, mutual action plans, and deal strategy with discipline.
Communicates clearly and confidently, both in writing and live conversations, and can make complex ideas feel simple and compelling.
Is proactive, competitive, curious, and excited to help build the sales motion at a fast-growing AI startup.

Skills

B2B SaaS sales
Enterprise sales
Consultative selling
Pipeline management
Forecasting
Communication

Location

Toronto

Work Type

Hybrid

Experience Level

4+ years

Salary/Compensations

Competitive salary + meaningful equity

Benefits

Meaningful equity
Direct customer impact
Work with cutting-edge AI tooling
High-growth environment
Health & wellness stipend
Annual international offsite
Team lunches & meetups

About the Company

Ribbon is building the future of hiring: faster, smarter, and built for scale.
Recognized by Fast Company as one of the Most Innovative Companies of 2026 and featured by The New York Times, BBC, Inc., and Bloomberg.
Helping employers find the right people 10× faster.
Our always-on voice AI interviewer screens candidates in minutes, identifies top talent automatically, and frees recruiters to spend time where it matters most.
Work with some of the largest Fortune 500s customers in automotive, self-storage, logistics, and high-volume hiring.
Helping teams dramatically reduce time-to-hire, raise candidate quality, and scale without adding headcount.