Enterprise Account Executive in Vaughan

Salary: $90,000 - $95,000 base + Commission (OTE ~$140,000)

Department: Sales

Reports To: VP of Sales

Location: Hybrid (Thornhill, ON)

Role Type: Permanent, Full-Time

About Us

At WellnessLiving, we empower health and wellness business owners to turn their passion into thriving businesses. Our mission-critical software supports thousands of entrepreneurs and millions of clients worldwide on their wellness journeys. We’re a customer-first company that values excellence, accountability, and adaptability, and we’re looking for people who thrive in a fast-paced environment and want to make a meaningful impact in the wellness industry.

Our culture is guided by four core values that shape how we work and grow together:

• Customer First – We approach every challenge with a deep commitment to our customers’ success and happiness.
• Excellence – We hold ourselves to a high standard and strive for exceptional execution in everything we do.
• Accountability – We take ownership of our decisions, actions, and results.
• Adaptability – We embrace change, stay flexible, and continuously evolve in a dynamic world.

If these values resonate with you and you meet the qualifications for this role, we’d love to hear from you!

About the Role

As an Enterprise Account Executive, you will be responsible for building and managing a pipeline of large fitness franchise and multi-location opportunities, with a primary focus on securing strategic, enterprise-level partnerships. You are a strategic, results-driven sales professional who excels in complex enterprise sales and is comfortable building opportunities from the ground up. You take a proactive, consultative approach, developing trusted relationships with senior stakeholders, navigating multiple decision-makers, and aligning solutions to meaningful business outcomes. Persistent, highly organized, and collaborative, you are comfortable managing long sales cycles while maintaining momentum from initial outreach through closing.

Responsibilities

• Build and manage a strong pipeline of enterprise fitness franchise and multi-location opportunities through consistent outbound prospecting.
• Identify and engage high-value accounts and key decision-makers across franchise leadership, operations, technology, and ownership.
• Develop and execute targeted outbound and account-based strategies to generate new enterprise opportunities.
• Develop tailored business cases, presentations, and proposals that demonstrate the value of our platform across a franchise organization or multi-location operation.
• Lead the full sales cycle, including discovery, product demonstrations, presentations, business cases, proposals, negotiation, and close.
• Navigate complex, long-term sales processes involving multiple stakeholders, locations, and decision-makers while maintaining consistent momentum and follow-up.
• Build trusted executive-level relationships that support franchise-wide adoption and long-term expansion.
• Maintain accurate CRM records, pipeline stages, next steps, forecasts, and expected close dates.
• Collaborate closely with leadership, marketing, product, implementation, and other internal teams, and travel for strategic meetings, headquarters visits, and industry events as needed.

What Success Looks Like

Success in this role means consistently building a strong enterprise pipeline, maintaining momentum through complex sales cycles, and developing trusted relationships with key decision-makers. You are proactive, persistent, and comfortable creating opportunities from the ground up, ultimately converting them into meaningful, long-term partnerships.

Skills & Qualifications

• 5–8 years of B2B sales experience, with a proven track record of closing complex, high-value enterprise deals.
• Strong experience prospecting, conducting discovery, developing proposals, and using a consultative sales approach.
• Demonstrated ability to build trusted relationships with VP- and C-level stakeholders and navigate multi-stakeholder buying processes.
• Exceptional verbal and written communication skills, including the ability to deliver compelling executive-level presentations.
• Experience selling end-to-end solutions and clearly articulating business value to sophisticated organizations.
• Experience within the Fitness & Wellness industry, ideally with exposure to franchise or multi-location businesses.

Why Work With Us

Join a passionate, fast-growing team focused on making a meaningful impact in the Fitness & Wellness industry. Enjoy a competitive compensation package, including vacation and benefits. Benefit from a flexible hybrid work environment with opportunities for professional growth and development. Be part of a collaborative culture that values creativity, innovation, and continuous learning.

WellnessLiving is an equal opportunity employer. Employment decisions are based on qualifications, experience, and business needs. We prohibit discrimination and harassment of any kind and consider all qualified applicants without regard to race, color, religion, creed, gender, gender identity or expression, sexual orientation, national origin, disability, age, genetic information, veteran status, marital or family status, or any other status protected by applicable law.

We utilize AI to generate summaries of interview notes as part of our candidate evaluation process. This helps ensure a fair and consistent review while maintaining a human-centered hiring approach.