Start Date: September 2026

About Optimity

At Optimity, we're on a mission to help people live healthier, longer, and happier lives — and we've built the tech to make it happen and power communities in-real-life through our amazing team.

Optimity is a gamified health and wellness platform with 7M+ members across North America. Our award-winning B2B platform combines behavioural science, gamification, and wearable data to help insurers, employers, and health organizations meaningfully engage their members across physical, mental, financial, and nutritional wellness.

We're a small, energetic team that is highly collaborative, moves fast, sweats the details, and genuinely cares about impact. Each team member “Optimizer” has plenty of autonomy, as well as clear goals and objectives. If you get excited about health, tech, and building communities that actually change behaviour at scale, you'll fit right in!

The role

We're looking for Account Executives and SDR/BDRs who bring hustle, creativity, and heart to the table. This isn't a paint-by-numbers sales job where you'll be expected to think on your feet, find your own paths to the right buyers, and build relationships that last. You'll own the full sales cycle, from identifying targets to closing deals, and you'll have the full weight of the team behind you when you need it.

If you're the type who reads about wellness on weekends, knows how to stay persistent without being pushy, and can turn a "not right now" into a real pipeline, we'd love to meet you.

What you'll do

• Research and identify events, conferences, expos, and community activations that align with Optimity's audience and brand
• Leverage a creative mix of outreach channels: LinkedIn, email, events, partnerships, warm intros, to get in front of the right people
• Run discovery calls and tailored demos that connect Optimity to each lead’s specific goals
• Manage and grow a healthy pipeline; stay organized, stay patient, keep momentum
• Collaborate actively with marketing, product, and leadership to sharpen your pitch and close smarter
• Pitch, negotiate, and close sponsorship packages that deliver real value on both sides
• Hit monthly and quarterly targets while thinking long-term about the relationships you're building
• Bring CRM discipline (HubSpot or Salesforce experience preferred) and share field insights that help the whole team get better

Who you are

• 3–5 years of B2B sales experience (events, sponsorships, partnerships, SaaS, and tech-enabled services preferred); you know how this world works
• Familiar with CRM tools and a structured sales process
• Resourceful and creative, you know how to get in the room, even when there's no obvious door
• Patient and persistent, you understand that great deals take time, and you don't give up easily
• Comfortable navigating ambiguity and adapting your approach on the fly
• Strong communicator, comfortable on calls, video, and email
• A natural connector who's comfortable reaching out cold and following up warm
• A natural collaborator who knows when to lean on the team and when to own it independently
• Self-motivated and comfortable working independently in a remote environment
• Genuinely passionate about health & wellness — you walk the talk (or at least walk the steps)
• Based in Canada and legally authorized to work

Nice to have

• Experience selling into Events and attending conferences
• An existing network of event organizers, venues, or brand partners
• Experience with wellness, HR, benefits, or insurance verticals
• Familiarity with insurtech, SaaS, or B2B2C business models

What we offer

• Fully remote; work from anywhere in Canada
• Flexible hours with real autonomy over how you manage your time
• Competitive base + uncapped commission (OTE $60k–125k+)
• A product you can feel good about selling
• A small, high-trust team where your voice actually matters
• Clear growth path as we scale

To apply:

Please send your resume to jlavoie@myoptimity.com and include a Loom video (3-5 minutes) answering the following 3 questions:

1. Walk us through your background in sales or business development; what have you sold, who were your clients, and what's a result you're genuinely proud of?
2. Tell us a bit about yourself beyond the resume: what drives you, and how does health & wellness show up in your life?
3. Why Optimity and why this role? What specifically excites you about building our events and sponsorship pipeline?