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FrontSail

Founding Sales & Customer Success Associate

Cambridge, ON, Canada
Greater Kitchener-Cambridge-Waterloo Metropolitan Area, Canada

Job type: Full-time
Apply by: Oct 29, 2026
Posting language: English
Posted: Sep 29, 2026

Apply About employer

Applications open in a new tab.

Original job description

Kitchener-Waterloo, Ontario

Commission-only + 0.25-0.75% equity | No base salary | Local, field-heavy role

FrontSail AI exists to make running a small business a lot easier. Our mission is to let anyone run and grow a business without drowning in the admin work around it.

Business owners should be serving customers, building and fixing things, selling, and growing their companies. They shouldn't 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 learns how a business operates and gradually handles more of the work around the actual job.

We're looking for someone to own the relationship with those businesses, from the first conversation to making sure FrontSail actually works for them.

The role starts before the sale and continues after it

You'll find local businesses, walk through their doors, call their owners and start conversations. You'll learn how they operate. What eats up their evenings? Where do leads disappear? Why aren't quotes going out? Which parts of the business are held together by WhatsApp messages, spreadsheets and somebody remembering to do something on Tuesday?

Then you'll work out whether FrontSail can help. You'll demo it, sell it, help the customer get started, and stay close enough to see what works and what doesn't. Then you bring what you learned straight back to the founders.

We think of sales and customer success as one job. If a customer buys FrontSail and never gets value from it, we don't count that as a successful sale, and we don't want someone whose involvement ends at the signature.

What you'll do

Find and approach local businesses across Waterloo Region: cold calls, email, referrals, events, and walking in the front door.
Talk with business owners and understand how their businesses actually run.
Spot the admin work, bottlenecks and missed opportunities that cost them time and money.
Demo FrontSail and help customers see where it fits in their business.
Own opportunities from the first conversation to close.
Onboard new customers and make sure they get real value out of FrontSail.
Keep in touch with customers as their needs change.
Notice when something isn't working before the customer quietly gives up.
Learn why prospects buy or don't, and why customers stay or leave.
Bring that feedback to the founders and help turn it into better product, positioning and process.
Try different industries, messages, offers and ways of selling until something clicks.
Help write the sales and customer-success playbooks that future FrontSail hires 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 none.

You'll help decide what FrontSail becomes

We're early, and we don't pretend the founders have figured everything out from behind their laptops. Customers will teach us a lot, and you'll be the person closest to them.

So we expect you to tell us when the pitch isn't landing, when customers are confused, or when we're solving the wrong problem. Tell us when three different businesses ask for the same thing without prompting, and when something we thought mattered turns out not to. We'd much rather hear the uncomfortable truth than have you argue for the product. The goal is something customers want to buy and keep using.

You'll also help build the company

This is one of our first hires, and the habits we set now become the company later: how we treat customers, how fast we respond when something breaks, how seriously we take feedback, how we sell, how we make decisions and how we treat each other. You'll shape that alongside the founders.

Joining this early has another upside. If FrontSail grows, this function grows with it. We'll need more people finding customers, onboarding them and managing relationships, and eventually processes, systems and a team around all of it. Someone will need to lead that. The person who learned the market firsthand, won the early customers, helped them succeed and wrote the first playbook will be well placed to do it.

We're not promising a title on a schedule. We are offering room to grow your responsibility as the company grows.

Who we're looking for

You like talking to people, and you're just as good at listening to them. You're comfortable calling a business that has never heard of us, or walking into a shop where nobody invited you. You can hear "no" twenty times without getting discouraged or robotic. When somebody says "this isn't useful to me," your first instinct is to ask why.

You care whether customers succeed after you've sold to them. You're curious enough to understand someone else's business, organized enough to follow through, and independent enough that nobody needs to hand you your next task every morning.

We care more about initiative, judgment, curiosity and how fast you learn than about an impressive résumé. Sales or customer-success experience helps but isn't required. Experience selling AI, SaaS or other tech is a strong bonus, and so is experience working with small businesses. Startup experience helps too.

You need to live in or near Kitchener-Waterloo and be able to get around the region regularly. A big part of this job happens face to face with business owners, away from the laptop.

Compensation

This is a commission-only role with equity. There is no base salary.

For recurring revenue from customers you bring in:

35% of collected recurring revenue in the customer's first year
Performance accelerators up to 45%
20% in the customer's second year
10% in the customer's third year
0.25-0.75% equity in FrontSail AI, depending on experience, scope and commitment, subject to vesting

Commission is uncapped.

We built commission around recurring revenue on purpose. If you find a great customer, help them succeed and they stay for years, you keep sharing in that relationship. It keeps both of us focused on customers who stay, not on how many contracts get signed.

This probably isn't for everyone

If you want an established company, a predictable salary, a defined territory, polished sales scripts and a manager handing you qualified leads, there are better jobs out there for you. This is earlier and messier than that.

But if you want to get close to customers, learn how businesses really work, sell AI, have a say in what gets built, and help shape a company while it's small enough for your decisions to matter, we'd like to meet you.

How to apply

Skip the generic cover letter. Send us a short introduction that answers three questions:

Why does this kind of role appeal to you?
Pick one local business in Kitchener-Waterloo you'd approach first. Why that one?
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 about how polished your résumé is. We want someone who wants to build this function and, eventually, lead what they helped create.

Apply About employer

More about this job

Responsibilities

Find and engage local businesses, understand their operational challenges, demonstrate and sell FrontSail, and manage customer onboarding and ongoing success. Share customer and prospect feedback with the founders, experiment with sales approaches, and help build the company’s sales and customer-success processes.

Requirements

Candidates must live in or near Kitchener-Waterloo, be able to travel around the region, and be comfortable initiating conversations with business owners and handling rejection. Sales or customer-success experience is helpful but not required; experience with AI, SaaS, technology, small businesses, or startups is a bonus.

Skills

Prospecting
Cold Calling
Sales
Customer Success
Customer Onboarding
Product Demonstrations
Relationship Management
Active Listening
Needs Assessment
Follow-Through
Customer Feedback
Sales Playbook Development
Communication
Initiative
Adaptability
Market Research

Benefits

Equity

Visa sponsorship

Not detected in the job text

Keywords

FrontSail AI
Artificial Intelligence
SaaS
Small Businesses
Sales
Customer Success
Prospecting
Cold Calling
Email Outreach
Referrals
Field Sales
Product Demonstrations
Customer Onboarding
Recurring Revenue
Commission
Equity
Customer Retention
Lead Generation
CRM
Work Orders
Quotes
Invoicing
Sales Playbooks
Customer Feedback
Market Research
Startup

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