VP of Sales (Saas)

WellnessLiving • Markham, ON

57d • Hybrid

About The Position

At WellnessLiving, we empower thousands of health and wellness business owners to turn their entrepreneurial dreams into reality. Our mission-critical software fuels their vision, supporting millions of clients around the world in their wellness journeys. With a deep commitment to putting our customers first, we foster a culture that values high performance, adaptability, and accountability. If you are a skilled professional who thrives in a fast-paced, customer-focused environment and are passionate about making a meaningful impact on the health and wellness industry, we would love to connect with you.

Our team is driven by four core values that shape everything we do. If you share these values and meet the qualifications outlined for this role, we encourage you to apply - we’d love to learn more about you!
Customer First – We approach every challenge with a customer-focused lens, driven by an obsession with our customers’ happiness and success.
Excellence – We approach every task, whether big or small, with a steadfast commitment to exceptional execution and the pursuit of greatness.
Accountability – We take full ownership of our decisions, actions, and outcomes – both successes and failures.
Adaptability – We recognize that sustained success demands that we be malleable and purposefully evolve, acknowledging that the world is dynamic and constantly changing.

The Opportunity
We are seeking a Vice President of Sales to lead and evolve our global sales organization, accelerate revenue growth, and build a world-class, performance-driven sales culture.
The VP of Sales will be a key role on our Senior Leadership team and will own end-to-end revenue generation, including strategy, execution, forecasting, and team leadership across SMB, mid-market, and enterprise segments. This is a hands-on leadership role for a proven SaaS sales executive who can build scalable systems, coach high-performing teams, and partner cross-functionally to deliver a seamless customer journey.

Requirements

• 10+ years of progressive SaaS sales experience, with significant leadership experience in a SaaS environment.
• Proven track record of scaling revenue, building sales teams, and implementing disciplined sales processes.
• Experience selling subscription-based software to SMB, mid-market and enterprise level customers; wellness and fitness, or vertical SaaS experience is a strong asset.
• Demonstrated success in both strategic leadership and hands-on execution.
• Exceptional leadership, coaching, and people development capabilities.
• Strong strategic thinking paired with operational rigor and data-driven decision-making.
• Excellent communication, negotiation, and executive presence.
• Understanding of modern SaaS sales metrics, CRM systems, and forecasting best practices.
• Ability to thrive in a fast-paced, scaling organization and adapt strategy as the business evolves.

Responsibilities

• Lead, mentor, and scale a high-performing sales organization, including BDR/SDRs, Account Executives, and Sales Managers and Directors.
• Establish a performance-driven sales culture with clear targets, quotas, accountability, coaching, and career development paths.
• Recruit, onboard, and develop top-tier sales talent aligned with WellnessLiving’s values.
• Develop and execute a comprehensive sales strategy aligned with WellnessLiving’s business objectives and growth plans.
• Define segment-specific go-to-market approaches across SMB, mid-market, and enterprise fitness and wellness businesses.
• Build and refine outbound and inbound sales motions, including prospecting, qualification, discovery, and closing, along with scripts, rebuttals and training.
• Own overall revenue performance, including new locations and expansion
• Build and manage a consistent, predictable sales pipeline with strong forecasting discipline and pipeline coverage.
• Achieve and exceed revenue targets through data-driven execution and continuous optimization.
• Stay updated and informed on industry trends, competitive landscape, and customer needs to inform sales strategy.
• Act as a senior executive presence in large, complex deals, supporting negotiations and deal closure when needed.
• Review, monitor, and continuously improve repeatable sales processes with defined stages, KPIs, and conversion metrics.
• Ensure effective use of CRM and AI sales tools to drive visibility, accuracy, and operational excellence.
• Partner with Sales Enablement, Marketing, and Product to ensure teams are equipped with the right messaging, tools, and training.
• Collaborate closely with Marketing on lead generation, campaign effectiveness, and conversion optimization.
• Partner with Finance and Operations on pricing strategy, sales budgeting, and ROI optimization.
• Provide regular, accurate sales forecasts, performance reports, and strategic insights to the CEO and executive team.
• Track and report on key metrics such as pipeline health, conversion rates, deal velocity, and forecast accuracy.

Benefits

• Competitive salary, vacation, and benefits package.
• Hybrid work environment with opportunities for career growth and development.
• Work in a culture that values creativity, collaboration, and continuous learning.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed