Full-time, permanent · Toronto office · Clinic visits and conference travel
We’re looking for an experienced, hands-on salesperson to bring in new business and own opportunities from prospecting through closing. You’ll work directly with the founders of a small, fast-moving healthcare technology team that values execution, ownership and follow-through.
Why Work Here
We believe doctors should be able to focus their time and attention on patient care. Pippen helps reduce the administrative work that gets in the way—from documenting encounters and drafting referrals to completing forms and supporting billing workflows.
You’ll help bring that value to more healthcare teams. Your work will connect clinics with a product that addresses a problem they experience every day, and you’ll see the impact of your efforts as those relationships become customers.
You’ll be a valued member of a small team, working closely with the founders and taking direct ownership of new-business opportunities.
Why This Role Matters
We already have a sales process that works, an existing pool of leads, and founders who can support demos and larger-account conversations. We’re looking for someone who will execute that process consistently and keep opportunities moving.
Your focus is new business. You’ll own outreach, follow-up, appointments, demos and deal progression through closing. Once an account closes, the rest of the team will take over ongoing account management through a clear handoff.
This is an individual contributor role reporting directly to the founders, with no people-management responsibilities.
What You’ll Do
- Work existing inbound inquiries, conference leads and researched prospects, and find additional opportunities through your own prospecting.
- Reach prospective customers through calls, emails, clinic visits, faxes and mailed outreach, using our established sales approach.
- Book appointments and product demos, and maintain consistent follow-up with clear next steps for each opportunity.
- Own your pipeline from initial contact through closing: qualify opportunities, coordinate the right conversations, address objections and move decisions forward.
- Work closely with our founders, drawing on their clinical and commercial expertise to deliver demos and close larger accounts.
- Attend conferences and visit clinics, turning conversations into opportunities and following through afterward.
- Coordinate a clear handoff to the team after closing so customers receive a smooth transition.
You Might Be a Fit If You
- Have more than five years of sales experience, with examples of opportunities you personally moved through the pipeline to closing.
- Take ownership of your work and follow through consistently, including when prospects are slow to respond.
- Are comfortable doing the daily work of sales: making calls, sending outreach, visiting clinics, booking meetings and maintaining follow-up.
- Communicate clearly, listen carefully and build relationships based on an accurate understanding of customer needs.
- Can learn a healthcare software product and explain its value in practical terms.
- Work well in a small, fast-moving team while managing your own priorities and pipeline.
- Can work in person from our Toronto office and travel to clinics and conferences.
Startup experience is strongly preferred. Healthcare sales experience is welcome but is not required.
How We Think About Performance
We believe consistent, purposeful work builds the foundation for strong sales outcomes. We place substantial weight on the execution you control: calls made, clinics visited, outreach completed, follow-up maintained, and appointments and demos booked.
We look at the frequency and volume of that work, the tactics you use, and how reliably you move opportunities forward. We also track the new business that results. Ownership means doing the work consistently and keeping every opportunity’s next step clear.
Compensation & Benefits
Guaranteed base salary: CAD $115,000 annually.
We offer a high, guaranteed salary with no commission, bonus or equity component.
We believe in paying people well for the consistent work that builds lasting customer relationships. Your salary gives you stability without making your income depend on whether an individual deal closes. We value sustained effort, execution and ownership, and believe those habits create the conditions for results.
Benefits include dental care, extended health care, vision care, paid time off and company events.
Apply Now
If you take pride in executing consistently, owning your pipeline and building customer relationships, we’d love to hear from you.
Send your résumé and a brief introduction to team@pippen.ai. Include an example of a new-business opportunity you personally moved through to closing, explaining your role, the actions you took and the result.
Pay: $115,000.00 per year
Benefits:
- Company events
- Dental care
- Extended health care
- Paid time off
- Vision care
Application question(s):
- Tell us about a new customer you personally won. How did the opportunity originate, what actions did you take from first contact through closing, and what was the result?
- Describe your weekly outreach and follow-up routine in a recent sales role. Which channels did you use, roughly how much outreach did you complete, and how did you keep opportunities moving?
Work Location: In person
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