FrontSail AI exists to make running a small business dramatically easier. Our mission is to enable anyone to run and grow a business by eliminating the administrative overhead aroundthe work they actually care about.
Business owners should be serving customers, building things, fixing things, designing thingsand growing their companies. They should not be spending their nights preparing quotes,updating work orders, managing a CRM, chasing leads, sending invoices, returning missed callsand keeping five different systems in sync.
FrontSail AI takes that work off their plate. We are building a virtual assistant thatunderstands how a business operates and handles more and more of the work around the corebusiness automatically.
The goal is not just productivity. It is to help business owners grow without turning everyevening into another shift, and give them more of their nights back for themselves and theirfamilies.
Now we are looking for someone to take that mission directly to local businesses.
This is not a normal SDR role You will not inherit a mature sales organization. You will help build one.
You will call businesses, walk into shops, meet owners, understand how their companiesactually operate, demo FrontSail AI, follow up and close customers.
But selling is only part of the job. You will also help us answer questions that matterenormously at this stage:
Why did someone buy?
Why did someone say no?
What part of our message is confusing?
What problems are business owners desperate to solve?
What should we change, and what should we build next?
Your customer conversations will directly influence our product, positioning, pricing andgo-to-market strategy.
What you’ll do Prospect local businesses throughout the Waterloo Region through cold calls, email,referrals, events and in-person outreach.




Speak directly with business owners and learn how they run their businesses.
Identify the administrative work wasting their time.
Demo and sell FrontSail AI, plus sibling products such as FrontSail Sites.
Own opportunities from first conversation through close.
Help recent customers get started, and stay close enough to understand whether FrontSail AI isactually helping them.
Bring objections, lost deals and customer feedback directly to the founders.
Experiment with industries, messages, offers and sales approaches.
Help create the sales process that future salespeople here will use.
You will work directly with the CEO and the founders. There are very few layers betweentsomething you hear from a customer and something changing in the company. Sometimes thereare zero.
You’ll also help build the company This is an early and important hire. The habits we build now will become the way the companyworks later: how we talk to customers, how we make decisions, how seriously we take feedback,how quickly we move and what kind of people we hire next. You will help shape that culturealongside the founders.
And if the company grows and you grow with it, the commercial organization will eventuallyneed people, processes and leadership. Someone will need to build and lead that function. Aperson who helped discover the market,



win the early customers and create the original salesplaybook will be in a very strong position to become that person.
We are not promising a title on a schedule. We are offering the opportunity to earnsubstantially more responsibility as the company grows.
Who we’re looking for You genuinely enjoy talking to people. You are comfortable calling businesses that have neverheard of us and walking into a shop where nobody invited you. You can hear "no" twenty timesand still be curious about what the twenty-first person might say.
You learn quickly, follow up relentlessly and do not need someone constantly telling you whatto do next. We care more about initiative, curiosity, judgment and the ability to learn thanabout an impressive résumé.
Previous sales experience is useful, but not mandatory. Experience selling AI, SaaS ortechnology products is a strong bonus. So is experience selling to small businesses, and so is startup experience.
You must be based in or around Kitchener-Waterloo and able to get around the regionregularly. This is not a remote sales role disguised as a local one. Talking to businessowners face-to-face is an important part of the job.
Compensation This is a commission-only role with equity. There is no base salary. For recurring revenuefrom customers you acquire:
35% of collected recurring revenue during the customer’s first year
Performance accelerators up to 45%
20% during the customer’s second year
10% during the customer’s third year
0.25–0.75% equity , depending on experience, scope and commitment, subject to vesting
Commission is uncapped. The recurring structure is intentional. We do not want someone whocloses a deal and disappears. We want someone who cares about finding the right customers,helping them succeed and building relationships that last.

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📌 Founding Sales & GTM Associate (Ontario)
🏢 FrontSail AI
📍 Ontario