Head of Sales: Mentorship, Mastery & Scale

Real Estate Webmasters • Nanaimo, BC

3d • CA$120,000 - CA$200,000 • Hybrid

About The Position

The Head of Sales role at Real Estate Webmasters (REW) is a capstone opportunity for an experienced SaaS sales leader. REW, a 22-year-old market leader with a $12M revenue base, is seeking a seasoned architect to fine-tune its sales model, implement a plug-and-play SaaS engine, and drive growth towards a $25M milestone. This role emphasizes mentorship, execution, and building a legacy, focusing on optimizing the sales engine, mentoring the next generation of leaders, and driving the company's strategic roadmap. The ideal candidate will bring institutional wisdom, a successor mindset, and a preference for systems over manual effort, thriving in a structured environment based on EOS (Traction).

Requirements

• Deep track record of success in SaaS leadership.
• Proficiency in understanding and influencing key SaaS metrics.
• Experience in building and leading sales teams.
• Grit and a process-oriented mindset to see initiatives through to completion.
• Resonance with the concept of being a multiplier and taking pride in team performance.
• Ability to lead from the Nanaimo headquarters.
• Experience with EOS (Traction) principles and structured leadership.

Nice To Haves

• Experience in leading through various market cycles.
• Proven ability to install proven systems at scale.

Responsibilities

• Apply a proven, "plug-and-play" SaaS sales model to the existing $12M revenue base.
• Recruit, onboard, and stabilize a focused pod of 3–5 Account Executives to reignite the new business engine.
• Provide high-level coaching to an established Account Management team to elevate their performance.
• Lead the sales strategy from $12M to $15M in 2026, establishing the operational foundation for the $25M milestone.

Benefits

• Base Annual Salary: $120,000 CAD.
• Total Annual Target OTE: $200,000 CAD+ (Uncapped).
• True Work-Life Balance.
• Legacy Building opportunity.
• Chance to play a pivotal role in the long-term success of a stable, BC-based tech pillar.

What This Job Offers

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