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Added 15 mins ago
T
Event Planning Specialist
Techo-Bloc
Longueuil, QC · Saint-Hubert, QC
- Full-time
…mapping the calendar, finding the right venues and lining up the contracts and vendors that set the team up for success. Our program includes two tours across about 40 cities, with a…
Added 44 mins ago
MD
Health Policy Assistant Division Director - Health Assistant Division Director
Minnesota Direct Care and Treatment
Saint-Paul, NB · St.-Paul, NB
- Full-time
…internal partners such as HR, Financial Management, MNIT, Grants & Contracts, and the Office of the General…
Added 59 mins ago
RM
Supervisor, Program Funding and Administration (EYCCS)
Regional Municipality of Peel
Brampton, ON
- Other
In leading this work, you will make recommendations to the Manager regarding the implementation of EYCC funds that align with both local and provincial direction, policies and reporting…
Added 1 hour ago
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Sales & Customer Success Associate (Founding Team)
FrontSail
Cambridge, ON · Greater Kitchener-Cambridge-Waterloo Metropolitan Area
- Full-time
Added 1 hour ago
GC
Art Buying and Photography Representation Expert
Gramian Consulting Group
Remote, Canada
- Contract
- Remote
Identify Contractual Risks: Flag potential issues involving contracts, model releases, property releases, insurance, production logistics and delivery requirements.
Added 2 hours ago
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Manager - Diagnostic Imaging
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- Full-time
As the Integrated Manager, you will oversee day-to-day operations of Diagnostic Imaging services at both Ross Memorial Hospital (RMH) and Haliburton Highlands Health Services (HHHS). Your…
Added 3 hours ago
YR
Business Systems and Data Specialist (Business Systems Support Specialist)
York Region (The Regional Municipality of York)
Newmarket, ON
- Contract
Reporting to the Program Manager, System Solutions and Data Management, this position is responsible for researching, planning, developing, and implementing data warehousing, business…
Added 3 hours ago
AH
Coordinator
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AB · Greater Edmonton Metropolitan Area
- Full-time
…Post Graduate trainees (PGTs) and projects as assigned by the Manager, Academic Medicine and or the Medical Affairs (MA) leadership team. Optimal portfolio management includes expertise in:…
Added 4 hours ago
PE
Structural Steel Estimator
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Calgary, AB
- Full-time
Amend estimates and manage changes throughout the project lifecycle in coordination with the Project Manager and client.
Added 4 hours ago
PE
Structural Steel Estimator
PTW Energy Services
Calgary, AB
- Full-time
Amend estimates and manage changes throughout the project lifecycle in coordination with the Project Manager and client.
Added 4 hours ago
EI
Site Project Manager
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Calgary, AB
- Full-time
The Site Project Manager owns end-to-end delivery of CoolIT liquid-cooling deployments at assigned customer sites, from project handoff and site readiness through commissioning, customer…
Added 5 hours ago
MS
manager, security
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Cambridge, ON
- Full-time
Plan, administer and control budgets for client projects, contracts, equipment and supplies
Added 5 hours ago
IF
inventory control manager
Iqbal Foods
Oakville, ON
- Full-time
Plan, administer and control budgets for client projects, contracts, equipment and supplies
Added 6 hours ago
CW
Inside Sales Account Executive
Canada's Wonderland
Vaughan, ON
- Full-time
…attendance and revenue, managing customer relationships, negotiating contracts, and exceeding sales…
Added 7 hours ago
GO
Facility Manager
Government of Nunavut Recruitment
Pond Inlet, NU
- Full-time
Facility Manager is responsible for program delivery of assigned communities in the Baffin, Region in political, social, and cross-cultural setting and oversees a multi-disciplinary group…
Added 7 hours ago
Maintenance Project Coordinator
Halton Region
Burlington, ON
Escalate overdue actions, unresolved documentation issues, and potential compliance concerns to the Maintenance Manager, Superintendent, or appropriate process owner.
Added 7 hours ago
TA
Automotive Finance Manager
Trotman Auto Group
Comox, BC
- Full-time
Looking for a high-earning Finance Manager opportunity where your expertise, attention to detail, and ability to structure the right deal are valued?
Added 8 hours ago
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Project Manager
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Contract
The Centre for Precision Psychiatry – Quebec (CPPQ) is seeking a project manager for our large-scale longitudinal mental health research project across three clinical research sites,…
Added 8 hours ago
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Clinical Research Coordinator - Regulatory Affairs (CIM)
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
Under the supervision of the Manager, Clinical Research Administration Centre for Innovative Medicine (CIM), the incumbent is responsible for supporting the submission of clinical research…
Added 8 hours ago
AT
Sales Business Development
Axis Technical Services
Burnaby, BC
- Full-time
We are seeking an experienced and well-connected Sales Business Development Manager to actively develop new business opportunities, expand our client base, and secure new projects and…
Added 8 hours ago
PR
Site Start-up Associate II (Health Canada CTA Submissions Expert)
Premier Research
Canada
- Full-time
…identified. May serve as the primary point of contact for the Project Manager, Clinical Lead, Regulatory Start-up Manager (or designee) during start-up on allocated…
Added 8 hours ago
AM
Pre-Planning Director
Arbor Memorial Inc.
Thorold, ON
- Full-time
Reporting to the Branch Manager, you will be responsible for promoting and providing funeral and cemetery pre-planning by contacting and meeting clients to pre-arrange their funerals and…
Added 9 hours ago
AM
Pre-Planning Director
Arbor Memorial Inc.
Thorold, ON
- Full-time
Reporting to the Branch Manager, you will be responsible for promoting and providing funeral and cemetery pre-planning by contacting and meeting clients to pre-arrange their funerals and…
Added 10 hours ago
PL
Health & Wellness Manager
Prima Living
Aurora, ON
- Full-time
The Health & Wellness Manager leads the development and delivery of wellness programs that promote the health, safety, and quality of life of residents and staff. This role oversees the…
Added 10 hours ago
I
Technical Sales Manager - AI Software & Services
Intersog
Remote, Canada
- Full-time
- Remote
We are looking for a Technical Sales Manager to drive sales of our AI-powered products and software services.

FrontSail

Sales & Customer Success Associate (Founding Team)

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

Full-time

Apply 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 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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