Director of Sales / Founding Account Executive

Gallea AI | Toronto, ON

Full-time, Permanent | In person | $250,000 to $300,000 CAD OTE Who We Are

Gallea AI builds AiOS, an Intelligent Operating System that makes an entire business conversational. Facing outward, it turns a company's website from something visitors have to navigate into something they can simply ask. Every answer comes back instantly, accurately, and in the brand's own voice, at any hour, along the brand's own conversion path.

Facing inward, it puts that same intelligence in the hands of the team, so a new hire at the front desk and a veteran manager at head office give the same approved answer to the same question. AiOS exists because we spent years inside the businesses it serves. Gallea AI began as an AI strategy and implementation consultancy, and across more than a hundred engagements we watched the same pattern repeat: companies buying AI tools that were never aligned to how their business actually runs.

AiOS is our answer to that, and it is now the product this company is built around. We're a credentialed IBM Business Partner, which means AiOS ships on enterprise-grade infrastructure with real governance behind it. That matters to the buyers we sell to.

They want the capability of AI without handing their brand voice, their data and their customer experience to a system nobody can account for. We're a small team defining a new category, and we're early. The product is real, the market is ready, and what we don't have yet is a commercial engine.

That is this role. About the Role

This is Gallea AI's first dedicated sales hire. There is no team to inherit, no playbook to run, and no inbound pipeline waiting for you. You are the commercial engine of the company from day one.

To be clear about the motion: this is a direct sales role first. For the foreseeable future, effectively every deal is one you source, pitch, negotiate and close yourself, through cold outbound and your own network. No partner is going to hand you an opportunity in your first year.

What you are also doing, at the same time, is seeding the channel that changes that. Over the first 12 to 18 months you'll recruit and sign the resellers, agencies and platform partners who begin by fulfilling and co-selling the deals you have already won, and who over time mature into sourcing their own. Carrying a direct quota while building that channel from zero is the genuinely hard part of this job, and it's why we need someone who has done both before rather than one or the other.

You'll sell into mid-market businesses across Canada and the United States,



with direct access to the Chairman and COO and real authority over how the go-to-market gets built. The ICP, the positioning and the partner model are hypotheses right now. You'll be the one who tests them against real buyers and tells us what's true.

What You'll Do

Direct sales, which is the majority of the job

- Source, pitch, negotiate and close AiOS deals yourself, start to finish
- Run the full outbound motion independently: email, LinkedIn and calling, at volume, without SDR support
- Build and iterate the AiOS sales playbook in real time, based on what actually works in market

Building the channel, which pays off later

- Recruit, sign and onboard the first reseller and agency partners from a standing start
- Bring partners in to fulfill and co-sell deals you have sourced, then develop them toward sourcing their own
- Build the partner enablement kit alongside our GTM advisor: pitch materials, demo flow, ROI model, objection handling

Commercial intelligence

- Feed real market signal back into strategy: objections, competitive intel, buyer language, vertical patterns
- Co-develop the ICP and positioning for AiOS with the Chairman, COO and GTM advisor, based on field evidence rather than assumption

Pipeline and reporting

- Own pipeline coverage, conversion rates and deal velocity against quota
- Represent Gallea AI credibly at the C-suite level with both clients and partner organisations What We're Looking For The person who succeeds here has built something from nothing before. Specifically, you have personally taken a company from $0 to $1M, and then from $1M to $5M. That track record is the single most important thing we're looking for.
- B2B SaaS sales experience in both the US and Canadian markets, with a transparent view of how the two buying motions differ
- A track record closing direct, full-cycle, from prospecting to signature, without a team underneath you
- Direct experience recruiting and signing channel partners from a cold start, not managing an inherited channel
- Experience operating as the first or only salesperson at a company
- A full outbound motion run independently: cold email, LinkedIn, cold calling
- Experience selling to mid-market buyers at the VP and C-suite level




- Comfort being the only salesperson in the building, selling a product that is still maturing
- A bias toward moving in days, not weeks. You would rather put a hypothesis in front of a buyer than perfect it internally
- Based in Toronto or willing to relocate. This is an in-person role Nice to Have
- Experience in our first-sprint verticals: E-commerce, Real Estate, Health & Wellness Supplements & Automotive Aggregators
- Background selling to consumer brands, ecommerce operators or DTC businesses
- Background in AI, MarTech or digital marketing SaaS
- Experience carrying a direct quota while standing up a partner channel at the same time
- Familiarity with IBM, Salesforce, HubSpot or similar enterprise platform ecosystems
- Experience designing a founding-partner or early-adopter program Who This Isn't For

We would rather be direct now than waste your time later. This role is probably not the right fit if:

- Your strongest numbers came at a company that was already well past $5M when you joined
- You have managed mature partner programs with established enablement, but never signed a partner cold
- You are looking for a channel role where partners bring you pipeline. That is where this is going, but it is not where it starts
- You have spent your career inside structured sales organisations with infrastructure already in place
- You need a finished product, a reference customer and a polished deck before you will go to market
- You have relied on SDRs or marketing-generated pipeline for most of your career Why Join
- The chance to build the commercial foundation of an AI company at the moment the market is ready for it
- Real ownership of the go-to-market strategy, partner model and sales playbook, rather than executing someone else's plan
- Direct work with a GTM advisor who has built a 300+ partner channel from scratch
- Direct access to the Chairman and COO, with no layers between you and the decisions
- Uncapped variable compensation on a book of business that does not exist yet. The ceiling is set by your own execution

We'll also be straight with you about the environment. It is fast-moving, ambiguous and founder-led. There is no marketing team generating inbound, no SDR handing off leads, and no pre-built playbook. If that reads as a warning, this isn't the role. If it reads as the appeal, we should talk. Compensation

$250,000 to $300,000 CAD OTE, split roughly 50/50 between base salary and variable compensation. Variable is uncapped. How to Apply

Apply through LinkedIn Easy Apply, or email your resume directly to [email protected].

📌 Director of Sales / Founding Account Executive (Toronto)
🏢 Gallea Ai
📍 Toronto