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Added 12 mins ago
TT
Gestionnaire de la réussite client - Customer Success Manager
trane technologies
Montreal, QC
- Full-time
Added 27 mins ago
L
Retail Sales Associates
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- Part-time
Deliver outstanding customer service by greeting customers, understanding their needs, and providing personalized product recommendations
Added 42 mins ago
W
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Added 42 mins ago
W
(CAN) Health and Beauty Team Associate
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Added 57 mins ago
WC
(CAN) Préposé aux caisses libre-service
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Supports the promotion of company sponsored programs, including credit card services, product protection plans, and charitable initiatives, when applicable.
Added 57 mins ago
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(CAN) Health and Beauty Team Associate
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Resolves customer issues and refers concerns to management where appropriate.
Added 1 hour ago
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Business Development Manager
Temu
Canada
- Full-time
Temu is seeking a highly motivated and experienced Business Development Manager to join our team. As a rapidly growing company, we are looking for talented individuals committed to helping…
Added 1 hour ago
(CAN) Self Checkout Attendant - part time
Walmart Canada
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Supports the promotion of company sponsored programs, including credit card services, product protection plans, and charitable initiatives, when applicable.
Added 1 hour ago
WC
(CAN) Health and Beauty Team Associate
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Added 1 hour ago
A&
Core Tax Incentives Manager – Technical
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Added 1 hour ago
WC
(CAN) Asset Protection Associate
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- Full-time
…investigations, escalates information to the Market Loss Prevention Manager in accordance with Company guidelines. Conducts or supports investigations related to internal theft, external…
Added 1 hour ago
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Customer Success Manager
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Toronto, ON
- Full-time
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Added 1 hour ago
FR
Assistant Project Manager
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Toronto, ON
- $70,000 to $110,000 CAD / year
- Full-time
Working alongside a Project Manager and Site Superintendent, you will help deliver projects from planning through to handover. You will take ownership of defined scopes while developing…
Added 1 hour ago
SD
Assistant Front Store Manager, Hourly Part Time Day Greenlight Requisition
Shoppers Drug Mart
Toronto, ON
- Part-time
To assist the Front Store Manager (FSM) in managing the human, physical and financial resources of the store and in ensuring that store objectives are achieved by focusing on improving…
Added 1 hour ago
SD
Assistant Front Store Manager, Hourly Full Time Day Greenlight Requisition
Shoppers Drug Mart
Toronto, ON
- Full-time
To assist the Front Store Manager (FSM) in managing the human, physical and financial resources of the store and in ensuring that store objectives are achieved by focusing on improving…
Added 1 hour ago
W
(CAN) Gérant de rayon, déchargement
Walmart
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…merchandise all in a safe and clean environment. This Department Manager will function as a lead of a team to strategically plan and execute duties based on workload and operational…
Added 1 hour ago
W
(CAN) Health and Beauty Team Associate
Walmart
Kemptville, ON
- Part-time
3. Resolves customer issues and refers concerns to management where appropriate.
Added 1 hour ago
W
(CAN) Gérant de rayon leader, marchandise générale
Walmart
Ste.-Foy, QC
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…priorities from the General Merchandise and Fashion Assistant Manager and the Store Management…
Added 1 hour ago
TC
Manager, Area Planning and Sales Inventory
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Added 1 hour ago
M&
Quality Technician
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Administratively support the initiatives of the Quality Manager, including data management and tracking.
Added 1 hour ago
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Director, Asset & Wealth Management, Portfolio Management
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Act as a senior credit and portfolio management lead for Asset & Wealth Manager borrowers and sponsor fund counterparties.
Added 1 hour ago
J
Staff Product Manager, Accounts & Payments
Jobgether
Canada
- Full-time
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Staff Product Manager, Accounts & Payments based in Canada.
Added 1 hour ago
HT
Financial Manager - PLM (Product Line Mgmt)
Husky Technologies
Bolton, ON
- Full-time
Title: Financial Manager - PLM (Product Line Mgmt)
Added 2 hours ago
C
Seasonal Retail Team Lead – Part Time
Clarks
Williamsburg, ON
- Part-time
- Temporary
Serve as the Manager on Duty for the store in the absence of the Store Manager and Assistant Manager
Added 2 hours ago
Solution Delivery Manager
Rogers Communications
Toronto, ON · Brampton, ON · Calgary, AB
We are seeking a Solution Delivery Manager reporting to the Senior Manager, Residential Solution Delivery. In this role as Solution Delivery Manager, you will provide end-to-end leadership…

FrontSail

Sales & Customer Success Associate (Founding Team)

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

Full-time

Apply on LinkedIn About employer

Applications open in a new tab.

Job details

Job type: Full-time
Apply by: Dec 6, 2026
Posting language: English
Posted: Nov 6, 2026

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 on LinkedIn About employer

More about this job

Responsibilities

Find and engage local businesses, understand their operational challenges, demonstrate and sell FrontSail, and guide customers through onboarding and ongoing success. Gather customer and prospect feedback, test sales approaches, and work with the founders to improve the product, positioning, processes, and future sales and customer-success playbooks.

Requirements

Candidates should live in or near Kitchener-Waterloo, be comfortable with in-person outreach and cold calls, and be able to work independently, listen well, and follow through. 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
Negotiation
Customer Retention
Market Research
Customer Feedback
Sales Playbook Development
Initiative
Communication

Benefits

Equity

Visa sponsorship

Not detected in the job text

Keywords

Artificial Intelligence
AI Assistant
SaaS
Software Development
Small Businesses
Sales
Customer Success
Prospecting
Cold Calling
Email Outreach
Referrals
In-Person Sales
Product Demonstrations
Customer Onboarding
Recurring Revenue
Commission
Equity
Customer Retention
Customer Feedback
Market Research
Sales Playbooks
Customer-Success Playbooks
CRM
Work Orders
Quotes
Invoices
Lead Management
Waterloo Region

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Jobs in Canada