Location: Kitchener-Waterloo, ON

Compensation: Commission-only + 0.25–0.75% equity

Commission: 35% of first-year recurring revenue, with accelerators up to 45%

Base salary: None

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 around the work they actually care about.

Business owners should be serving customers, building things, fixing things, designing things and growing their companies.

They should not be spending their nights preparing quotes, updating work orders, managing a CRM, chasing leads, sending invoices, returning missed calls and keeping five different systems in sync.

FrontSail takes that work off their plate.

We’re building an AI assistant that understands how a business operates and handles more and more of the work around the core business automatically.

The goal is not just productivity.

It is to help business owners grow without turning every evening into another shift — and give them more of their nights back for themselves and their families.

Now we’re looking for someone to take that mission directly to local businesses.

This is not a normal SDR role

You won’t inherit a mature sales organization.

You’ll help build one.

You’ll call businesses, walk into shops, meet owners, understand how their companies actually operate, demo FrontSail, follow up and close customers.

But selling is only part of the job.

You’ll also help us answer questions that matter enormously 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?

What should we build next?

Your customer conversations will directly influence our product, positioning, pricing and go-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 and other FrontSail services.
- Own opportunities from first conversation through close.
- Help recent customers get started and stay close enough to understand whether FrontSail is actually 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 FrontSail salespeople will use.

You’ll work directly with the CEO and the founders.

There are very few layers between something you hear from a customer and something changing in the company.

Sometimes there are zero.

You’ll also help build the company

This is an early and important hire.

The habits we build now will become the way FrontSail works 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’ll help shape that culture alongside the founders.

And if FrontSail grows and you grow with it, the commercial organization will eventually need people, processes and leadership.

Someone will need to build and lead that function.

A person who helped discover the market, win the early customers and create the original sales playbook 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 earn substantially more responsibility as the company grows.

Who we’re looking for

You genuinely enjoy talking to people.





You are comfortable calling businesses that have never heard of us and walking into a shop where nobody invited you.

You can hear “no” twenty times and still be curious about what the twenty-first person might say.

You learn quickly, follow up relentlessly and don’t need someone constantly telling you what to do next.

We care more about initiative, curiosity, judgment and the ability to learn than about an impressive résumé.

Previous sales experience is useful, but not mandatory.

Experience selling AI, SaaS or technology products is a strong bonus.

Experience selling to small businesses is a strong bonus.

Startup experience is another.

You must be based in or around Kitchener-Waterloo and able to get around the region regularly.

This is not a remote sales role disguised as a local one. Talking to business owners 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 revenue from 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 don’t want someone who closes a deal and disappears.

We want someone who cares about finding the right customers, helping them succeed and building relationships that last.

How to apply

Skip the generic cover letter.

Send us a short introduction answering three questions:

1. Why does this kind of role appeal to you?
2. Pick one local business in Kitchener-Waterloo you would approach first. Why that one?
3. Take a look at frontsail.ai. What would you change about our message, content, illustrations or positioning to make it more compelling to local business owners — and why?

We care more about how you think, communicate and take initiative than how polished your résumé looks.

📌 Founding Sales & GTM Associate (Waterloo)
🏢 FrontSail
📍 Waterloo