Founding Enterprise Account Executive, Voice AI

About Sadie

Sadie is an enterprise voice AI platform built to replace legacy IVR systems and transform how large organizations handle customer interactions at scale. Headquartered in Montreal and owned by Valsoft Corporation, Sadie delivers intelligent, conversational voice experiences that operate 24/7, reducing operational costs, capturing revenue, and elevating the customer experience without adding headcount.

We are moving upmarket. Our next chapter is selling to large enterprise accounts, where the commercial opportunity is significant and the product impact is measurable.

Sadie is part of Fluent Software Group (a Valsoft Corporation operating group), a global acquirer and operator of vertical market software businesses. We focus on specialized industries where expertise creates lasting advantages.

The Role

This is a founding enterprise sales hire. You will be the first person dedicated to building pipeline for Sadie's large enterprise segment, accounts with complex contact center environments, high inbound call volume, and the organizational scale to justify a voice AI deployment.

There is no inherited territory, no warm pipeline waiting, and no playbook yet. You will build all three. If that sentence excites you, read on. If it gives you pause, this is not the right seat.

You will hunt net-new logos, run the full sales cycle, and where strategic accounts warrant it, retain commercial ownership post-close to drive expansion. Vertical focus is open, we are prioritizing account size and deal quality over industry specialization in this early phase.

Location: Remote (Montreal)

The salary range for this role is $80,000 - $100,000 CAD base salary plus commission calculated on Total Contract Value (TCV). Final compensation will be determined based on experience, skills, and location.

What You'll Do

Pipeline Building (Hunter)

• Identify and systematically prospect large enterprise accounts across industries.
• Build outbound sequences, leverage your network, attend relevant industry events, and develop partner and channel relationships to generate qualified pipeline.
• Run sharp discovery to assess decision-maker access, technical fit, budget cycle, and strategic urgency before committing deep cycle resources.
• Maintain a pipeline that is 3–4x your quarterly target at all times.

Deal Execution (Closer)

• Own the full sales process from first meeting through signed contract on deals you originate
• Navigate complex, multi-stakeholder enterprise environments, CX leadership, IT, procurement, and C-suite, simultaneously.
• Build compelling business cases anchored to cost reduction, call deflection rates, CSAT improvement, and revenue capture.
• Manage RFP processes, security reviews, and legal cycles without losing deal momentum.
• Hit and exceed quarterly TCV targets.

Account Development (Nurturer)

• Retain commercial ownership of strategic accounts post-close to drive expansion and renewal.
• Act as the voice of the enterprise customer back into product and leadership.

What We're Looking For

• B2B enterprise sales experience, with a demonstrable track record of closing 6- and 7-figure deals.
• Experience selling into large enterprise accounts in complex environments strongly preferred.
• Background in voice AI, conversational AI, contact center technology, or CX automation is a significant advantage.
• Proven ability to build pipeline from scratch, you have done a founding or early enterprise sales role before and you know what that requires.
• Comfortable running long sales cycles (6–18 months) with multiple stakeholders and procurement gatekeepers.
• Strong commercial instincts, you can build a business case, defend pricing, and negotiate enterprise terms.
• CRM discipline: you run your pipeline in a system, not in your head.
• Bilingual (English/French) is an asset given our Montreal base and Canadian enterprise market.

Why Sadie?

• You are the first enterprise sales hire in this segment, territory is wide open.
• Backed by Valsoft Corporation, a profitable, acquisition-driven software group, stable platform, no dependency on the next funding round.
• Voice AI for enterprise is a high-conviction, high-growth category, the technology is ready, the buyer is ready, and the market is early.
• The upside is real and uncapped for someone who can close at this level.
• Direct line to product and leadership, you will shape how this market motion gets built.

Join Us

Join Sadie and play a key role in bringing AI-powered voice technology to enterprise organizations while helping define the future of our enterprise business.

We use AI-powered tools (including transcription and automated note-taking) during portions of our interview process to support a consistent and thorough candidate experience. Candidates who require alternative accommodation may request it at any stage of the recruitment process.

Fluent Software Group is committed to building diverse, equitable, and inclusive teams. We welcome applications from candidates of all backgrounds, identities, and experiences, and all qualified applicants will be considered without regard to race, gender, age, disability, religion, sexual orientation, or any other protected characteristic.

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