Head of Sales: Mentorship, Mastery & Scale

Realestatewebmasters; Nanaimo; On-site; CAD 150,000 - 210,000; Full time

Benefits offered by this job

Hybrid work schedule

Uncapped incentive potential

Job summary

Real Estate Webmasters (REW) is seeking a Head of Sales: Mentorship, Mastery & Scale. Location: Downtown Nanaimo, BC (Hybrid - 3 days in office/ week minimum). The role focuses on mentoring the sales organization, refining the SaaS playbook, and driving growth toward the $25M roadmap.

You will lead from our Nanaimo headquarters, leverage EOS discipline, and build a scalable sales engine while prioritizing mentorship and execution for lasting impact.

Qualifications

• Proven SaaS leadership with metrics that matter.
• Mentor internal talent to scale performance.
• Experience in building scalable sales engines and playbooks.
• Exposure to EOS/Traction driven organizations is a plus.

Responsibilities

• Apply a plug-and-play SaaS sales model to the existing $12M base.
• Recruit, onboard, and stabilize a focused pod of 3-5 Account Executives.
• Coach the Account Management team to reach higher performance tiers.
• Lead the 2026 roadmap from $12M to $15M and set foundations for $25M.

Skills

SaaS leadership

Mentorship

Team building

Sales strategy

Job description

Head of Sales: Mentorship, Mastery & Scale

Location: Downtown Nanaimo, BC (Hybrid - 3 days in office/ week minimum)

The Mission: Optimize the Engine. Mentor the Next Generation. Drive the $25M Roadmap.

The Rewards

• Base Annual Salary: $120,000 CAD.
• Total Annual Target OTE: $200,000 CAD+ (Uncapped).
• True Work-Life Balance: We believe in professional excellence and work-life balance.
• Legacy Building: A chance to play a pivotal role in the long-term success of a stable, BC-based tech pillar.

Our Core Values

At REW, we live and breathe these values. We expect our Head of Sales to embody them every day:

• Innovation: Staying curious, open-minded, and always looking for ways to do things more efficiently.
• Customer Success: Caring deeply about delivering great service to both internal and external clients.
• Always be Awesome: Remaining positive and helpful even when days are tough; supporting colleagues in a way that elevates the team.

The Culture: Accountability & Execution

We run on EOS (Traction) and value structured leadership. We want a leader who thrives on mentorship and execution-the person who gets joy from clearing obstacles for their team and crossing the finish line on revenue targets: a true multiplier.

The Opportunity: The Capstone of a Career

You’ve spent your career mastering the complexities of SaaS sales. You’ve built the playbooks, led through various market cycles, and seen what "great" looks like at scale. Now, you’re looking for a role where your value is defined by your judgment, your mentorship, and your ability to install proven systems.

Real Estate Webmasters (REW) is a 22-year-old market leader with a $12M revenue base and a culture built on EOS (Traction). We aren't looking for a "disruptor" to reinvent our identity; we are looking for a Seasoned Architect to fine-tune our sales model, implement a plug-and-play SaaS engine, and steward our growth to $25M.

Why This is Your Next (and Perhaps Best) Move

This role is designed for a leader who has moved past the need for the limelight and now finds professional fulfillment in building people. You demonstrate Institutional Wisdom: You bring a "been there, done that" calmness to the table. You hit the ground running because you’ve seen these patterns before.

• The Successor Mindset: You aren't just managing a team; you are building a legacy. You are excited to mentor internal talent and eventually hand over a perfectly tuned engine to the next generation of leadership.
• Systems Over Sweat: We value the discipline of EOS. You love the clarity of Level 10 meetings and the "math" of sales because it creates a predictable, stress-free environment for your team to win.

Your Responsibilities

• The SaaS Playbook: Apply your proven, "plug-and-play" SaaS sales model to our existing $12M base.
• Net-New Growth: Recruit, onboard, and stabilize a focused pod of 3-5 Account Executives to reignite our new business engine.
• Mentorship & Stability: Inherit an established Account Management team and provide them with the high-level coaching they need to reach the next tier of performance.
• Strategic Roadmap: Lead the charge from $12M to $15M in 2026, setting the operational foundation for the $25M milestone.

Who You Are

• The Experienced Leader: You have a deep track record of success in SaaS leadership. You know the "SaaS metrics that matter" and how to move them.
• The Mentor: You resonate with the concept of being a Multiplier. You take more pride in your team’s performance than your own personal accolades.
• The Finisher: You don't just start initiatives; you have the grit and the process-oriented mindset to see them through to completion.
• Island Ready: You are looking for a high-impact role that respects your life outside of work. You want to lead from our Nanaimo headquarters and enjoy the balance that 22 years of stability provides.