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Sadie

Account Executive

Canada

Job type: Full-time
Posting language: English
Posted: Sep 24, 2026

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Original job description

Description

Sadie is building technology for hospitality.

We're looking for an account executive to win new restaurant customers around major cities in Canada, and to run every deal yourself from the first lead to the signed agreement.

This is a field role. You'll find restaurants through outbound outreach, networking and on-site visits, then meet owners in person and show them Sadie working on their own calls. You'll work with onboarding and customer success, so that what you sell goes live well. You'll carry monthly and quarterly targets and own the forecast behind them.

You decide where to spend your time and which deals to pursue, within agreed pricing and terms. AI should be part of how you work. Use it to research restaurants before a visit, prepare demos, draft proposals and follow-ups, and plan your territory. You're responsible for the quality of everything that goes out under your name.

What we value

Sound judgement about which deals are real.
Taking responsibility for your number and finishing work without being chased.
Understanding how a restaurant makes money, and caring whether Sadie improves it.
Curiosity about why a deal was lost, and a willingness to change your approach.
The honesty to say a deal is slipping before the forecast says it for you.

What you'll do

Win new restaurants, from first visit to signed agreement

Most of your time goes on live deals, and most of those deals happen in person. You'll sit down with owners and general managers in their restaurants to learn how the phone is handled today: who answers it, what gets missed during service, and what those missed calls cost in bookings and orders. Then you'll demo Sadie against that picture.
You'll scope what the restaurant needs, write the proposal, negotiate terms and get the agreement signed.
Most of the judgement is in qualification. A good demo with someone who can't sign, or a restaurant Sadie can't serve yet, costs you weeks. You're expected to spot that early and move on.

Build your own pipeline across your territory

You'll generate your own leads through outbound outreach, networking and on-site visits. That means planning which neighbourhoods and restaurant groups to work, walking in at the right time of day, and following up until you get a meeting.

Hit your targets with a forecast you can defend

You're measured against monthly and quarterly sales targets, and the expectation is that you hit them consistently. You'll keep every opportunity accurate in HubSpot, so that stage, value and close date mean something to the people who plan around them.

Represent Sadie where restaurant people meet

You'll attend local industry events, restaurant meetups and trade shows across your geography. You'll decide which ones are worth the evening, run the conversations there, and turn them into meetings within the week.
For a lot of operators, you'll be the first person from Sadie they meet. What they hear from you is what they'll repeat to other owners.

Hand over accounts that go live well

The restaurant buys Sadie, but the guest ringing to book a table decides whether it works. You'll give onboarding and customer success a written record of what you promised, what the owner expects, and what could go wrong.
If you oversell, the owner finds out on a Friday night and the guest pays for it. Set expectations you can stand behind.

What you'll bring

At least 2 years in a closing sales role, selling software or services to businesses.
A record of meeting targets, and the ability to explain how you did it.
Experience running the whole cycle yourself, from prospecting through to signature.
Comfort with in-person selling, including cold visits and demos in front of a busy owner.
Strong discovery skills. You can find out what an operator needs in fifteen minutes between services.
Clear written communication. Your proposals and follow-ups are accurate and short.
An honest forecast. You'd rather call a deal lost than carry it for another month.
You use AI every day for research, preparation and drafting, and you check what it produces.
You organise your own week across a territory and follow through without being managed.

Useful experience

Selling to restaurants or other hospitality operators.
Working in a restaurant yourself, front of house or in management.
Selling reservations, POS, telephony or other restaurant technology.
An existing network among restaurant owners in your territory.
Selling AI products to non-technical buyers.
Being an early sales hire at a startup.

Who will enjoy this role

You like finding out how a business really works. When an owner says they miss calls at seven on a Saturday, you want to know how many, what those calls were for, and what happened to the guest who hung up.

In a single week you might walk into six restaurants before lunch service, run a demo at a bar between shifts, spend an evening at a trade show, and sit with onboarding to sort out an account you signed. Your schedule follows the restaurant day, and some of your best conversations will happen at three in the afternoon or late at night.

The hard parts are specific. Owners are busy and sceptical, and many will turn you away mid-service. You'll hear no far more often than yes, and you'll still need to be back through the next door the same afternoon. Some of the material you'd expect to have, such as local case studies or a settled playbook, may not exist yet, and you'll help build it while carrying a number.

Why this role matters

Sadie is building technology for hospitality. Restaurants lose revenue to calls nobody picks up, and our product exists to answer them.

This role is how Sadie reaches the restaurants in your geography. You decide who to visit and how each customer starts. The agreements you sign affect revenue, what onboarding and customer success inherit, and what a guest hears when they ring to book a table.

You'll own new restaurant business across your territory, with the authority to decide how Sadie wins it.

#Sadie

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More about this job

Responsibilities

Generate and close new restaurant business across an assigned Canadian territory through outbound outreach, networking, in-person visits, demonstrations, proposals, and negotiations. Manage targets and HubSpot forecasts, represent Sadie at industry events, and provide accurate handoffs to onboarding and customer success.

Requirements

Applicants need at least two years of closing sales experience selling software or services to businesses, a record of meeting targets, and experience managing the full sales cycle. They should be comfortable with field sales and cold visits, skilled at discovery and concise written communication, able to forecast honestly and organize their territory independently, and use AI tools while checking their output.

Skills

Full-Cycle Sales
Prospecting
Pipeline Generation
Territory Planning
In-Person Selling
Product Demonstrations
Discovery and Qualification
Proposal Writing
Negotiation
Sales Forecasting
HubSpot
Restaurant Technology Sales
Customer Handoffs
AI-Assisted Research and Drafting
Written Communication
Relationship Building

Visa sponsorship

Not detected in the job text

Keywords

Sadie
Hospitality Technology
Restaurant Sales
Software Sales
Business-to-Business Sales
Full Sales Cycle
Outbound Outreach
Lead Generation
Territory Planning
In-Person Sales
Cold Visits
Product Demonstrations
Sales Qualification
Proposal Writing
Contract Negotiation
Monthly Sales Targets
Quarterly Sales Targets
Sales Forecasting
HubSpot
Restaurant Operations
Reservations
Restaurant Technology
Artificial Intelligence
Onboarding
Customer Success
Trade Shows

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