Our mission is to help small businesses run themselves. We’re starting with doctors’ offices, building autonomous systems that handle busywork and complete the workflows that keep the office moving every day. Our team is small, flat, and ambitious. We value craft, intellectual rigor, and direct communication.

About the role As a GTM Associate at Lassie, you'll create the first spark of demand. You'll identify promising doctors' offices, run thoughtful outreach you'd want to receive yourself, schedule demos, and help us learn which messages actually land with small businesses.

What you'll do

Build lists of promising doctors' offices and run thoughtful outreach across email, phone, social, events, and more

Experiment with messages, segments, and channels to learn where demand is strongest

Run early discovery conversations to understand who's working in the practice, how the office operates, and where Lassie may or may not fit

Partner closely with Account Executives to schedule demos with offices that meet Lassie's ideal customer profile

Keep the GTM engine organized, measured, and moving

What we're looking for





You have 1–2 years of SDR or BDR experience

You move rapid, think fast, and improve with every rep

You never give up, with a smile on your face

You build real rapport with a busy doctor in 90 seconds, and they feel it

You're self-aware, flag what isn't working, and know how to improve

You're excited about helping a small business run itself

Location:

This is an in-person role,

5 days a week

in our Toronto office. We value the connection, collaboration, and shared learning that come from working together.

Compensation and Benefits

Compensation:

$100,000 - $110,000 on-target earnings (OTE) plus a generous pre-IPO equity package.

Individual offers

will reflect your experience, relevant skills, and the scope of the role.

Joining us To start, you'll have a handful of conversations with our team and founders. If there is mutual excitement, we'll invite you to the office where you'll work on a small project and meet the team.

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📌 GTM Associate (Winnipeg)
🏢 Lassie
📍 Winnipeg