Head of Sales: Mentorship, Mastery & Scale

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 , 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.