Who we are

At Cherry Health, we are transforming healthcare in North America. Our platform is the country's most advanced healthcare jobs network, built to empower healthcare professionals in finding their dream careers. We are a fast growing company made powerful by our small but phenomenal team! We work collaboratively, quickly and with a high level of personal accountability and transparency. If you're curious, driven and motivated, this might be a great opportunity for you!

Our team is based in Calgary, AB and we work in a hybrid model, minimum 1 day/week in office.

What makes this role interesting

This is not your typical AE role.

We're looking for a creative, proactive, and driven self-starter who's ready to roll up their sleeves and shape the future of our growth. You'll be joining as the first AE hire, reporting directly to the CEO, with the opportunity to lead both execution and strategy - and to build a sales team around you as we grow.

Our clients are employers in healthcare; from the smallest clinic to the largest health authorities, as well as companies that want to market to these organizations and practitioners. Working with the team, you will focus on both of these client types at different levels.

What you'll be doing:

• Develop outbound strategies and collaborate on inbound efforts
• Lead sales planning, forecasting, and growth strategy
• Own the full sales cycle: from prospecting to close
• Build strong relationships with customers and key decision makers
• Analyze pipeline data and iterate on what's working (and what's not)
• Collaborate closely with Marketing, Product, and Customer Success
• Help define our Ideal Customer Profile (ICP), refine messaging, and build repeatable playbooks
• Plan for and attend conferences and events as required
• Hire, train, and mentor future members of the sales team

What we're looking for

• 8+ years of experience in B2B sales, ideally at a startup or in a full-cycle sales role
• Experience in the recruitment industry is a strong plus
• Proven ability to hit or exceed quota consistently
• Experience building sales strategy, planning, and processes
• Creative and entrepreneurial mindset - you enjoy building new things from scratch
• Highly organized with strong follow-through
• Excellent communication and storytelling skills
• Highly curious and consultative in your approach both internally with our team and as an AE
• Comfortable working in a fast-paced, ambiguous environment
• Experience working with government health authorities or healthcare teams is a strong asset

Why join Cherry Health?

At Cherry Health, we believe in empowering our team to do their best work while fostering an environment that values growth, collaboration, and well-being.

• Be the founding AE and a key voice in how we grow
• Real ownership over sales strategy, planning, and execution
• Work directly with the leadership team and make a company-wide impact
• Competitive compensation and equity
• A product that customers love and a market that's just getting started

If you're hungry for impact, excited by ownership, and ready to help build something from the ground up - we want to hear from you.