Account Executive

Account Executive

About Us

Toboggan Labs is a boutique consultancy building at the intersection of AI and healthcare. We solve challenging human problems by applying cutting-edge technology and domain understanding.

About the role

We’re seeking an Account Executive to help drive our next phase of growth, with a strong focus on expanding our client base across Canada, starting in Toronto and the surrounding region.

This is a hunter role. You’ll be responsible for building pipelines from the ground up, opening new doors, and closing complex consulting engagements. You’ll sell high-value, consultative work — not off-the-shelf products — partnering closely with our technical and delivery teams to shape solutions that solve real client problems.

You’ll also play a key role in strengthening our presence in the Canadian market through relationships, events, partnerships, and thought leadership.

Your work will consist of:

• Pipeline development — Sourcing new opportunities through warm outreach, leveraging your network, attending industry events, and building relationships with potential clients. You’re energized by opening doors and creating momentum.
• Consultative selling — Deeply understand client challenges, qualify opportunities, and articulate how our services map to business outcomes. Partner with solution architects to shape proposals and scopes of work.
• Deal management — Own the full sales cycle from first conversation to signed contract, including pricing, negotiations, MSAs, and SOWs, alongside our leadership team to price engagements appropriately.
• Market development — Identifying interesting case study material from our engagements and working with our team to publish and promote our work. Attending and speaking at industry events. Building relationships with technology vendors and partners to co-sell.
• Strategic growth — Contributing to our sales strategy, particularly as we continue to move upmarket and expand into new healthcare verticals. Sharing insights on customer needs, competitive dynamics, and emerging opportunities.

About you

We are seeking someone with a strong track record of selling complex consulting or professional services, not just products off a shelf, you know how to sell work where value, scope, and approach are co-created with the client. You’re comfortable navigating ambiguity, engaging senior stakeholders, and representing technical teams with credibility.

Most importantly, you’re a hunter. You don’t need a pipeline handed to you — you know how to build one.

We want you to apply if you:

• Have 5+ years of experience in technology services sales, with solid experience selling consulting or professional services rather than products.
• Have a proven track record of pipeline development and consistently hitting or exceeding quota.
• Understand how to apply AI and other emerging technologies to business problems. You don't need to be able to build the solution, but you need to understand it well enough to have credible conversations.
• Are an excellent communicator and relationship builder.
• Thrive in environments with complexity and ambiguity. Every deal is different, and you thrive in that environment.
• Enjoy building leverage through automation, tooling, or systems (e.g. low-code automation, Claude skills/custom GPTs, and/or vibe-coding).
• Are willing to travel from time to time, and attend local events frequently.

Bonus points if you:

• Have a technical background in software development or data science.
• Have experience selling to healthcare, biotech, life sciences, or other heavily regulated industries.
• Have experience building a sales strategy to move upmarket, particularly transitioning from startup clients to SMB and enterprise accounts.

All of our job postings describe a bit of a unicorn. If you’re kind of a “narwhal,” please apply anyway. You don’t need to meet all the requirements, let alone the bonus criteria. While experience and skill sets are valuable, growth potential and attitudes are equally important. We are usually flexible on levels or can advise you when a more relevant posting opens.

What we offer

Toboggan Labs values the diversity of the people it hires and serves. Diversity, for us, means fostering a workplace in which a person's differences are recognized, appreciated, respected and responded to in ways that fully develop and utilize their talents and strengths.

In addition:

• Home office/technology budget;
• Yearly professional development budget;
• Company matching RRSP after 1 year;
• From Day 1
• 100% employer-paid health & dental insurance  including a yearly bank of coverage for complementary medicine (Acupuncture, osteopathy, massage therapy, naturopathy, psychology, etc.); 
• Life, long & short-term disability insurance;
• Parental leave top-up (8 weeks), regardless of path to parenthood.

Compensation

The base pay range for this role is CA$100,000 – CA$120,000 per year (OTE would be 200,000k+ and commission is uncapped). Final compensation will be set fairly and thoughtfully based on experience, expertise, and alignment with the role’s responsibilities.