Enterprise Account Executive

Own the enterprise sales journey from first conversation through close. As Ribbon’s Enterprise Account Executive, you’ll work directly with Talent, HR, Operations, and business leaders to help them understand how AI can transform the way they hire.

You’ll be responsible for building pipeline, running consultative sales cycles, deeply understanding customer hiring challenges, and closing 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.

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, we’re 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.

We work with some of the largest Fortune 500 customers in automotive, self‑storage, logistics, and high‑volume hiring, Ribbon is helping teams dramatically reduce time‑to‑hire, raise candidate quality, and scale without adding headcount.

• 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.

• 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.

• Competitive salary + meaningful equity. We want you thinking like an owner because you are one.
• Direct customer impact. You’ll shape how companies adopt AI in one of the most important parts of their business: hiring.
• Cutting‑edge tech. Work with the latest AI tooling, not yesterday’s stack.
• High‑growth environment. Join at the inflection point of a fast‑scaling, VC‑backed company.
• 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.
• Team lunches & meetups in Toronto. A flexible hybrid work environment.

Location Toronto, ON, Canada

Work Mode On‑site

Seniority Mid‑Senior

Function Sales & Business Development

Company Size 11‑50 employees

Skills Account Planning Consultative Selling Customer Relationship Management Forecasting Negotiation Problem Solving Stakeholder Management