Territory Sales Executive

About The Massimo Group
We coach commercial real estate brokers. That is all we do.
We are the premier coaching organization in the industry. In 18+ years we have worked with more than 4,000 CRE professionals, from brand-new agents to established producers. We run a done-with-you coaching model built on the Massimo Methods, delivered by CRE Certified Massimo Coaches and led by our founder, Rod Santomassimo, a five-time bestselling author.
Our clients want more income in less time. You will sell that outcome to people who can measure it.
The Role
You own a territory. You find the brokers in it, start the conversations, book the consults, run them, and close them. This is an independent contractor position.
This is a hunter role. You secure your own consults through outbound effort (calls, LinkedIn, email, referrals, local market events), then convert them on Zoom. If you want a defined territory, a proven product, and uncapped commission on high-ticket sales, keep reading.
Your Territory
Your territory is everything west of the Mississippi River: roughly 60,000 commercial real estate brokers. That is a large market to work, and you decide how to work it.
New clients are yours. Any broker in your territory you sign to Scale, Accelerator, Start, or Membership is a commissionable sale.
Upgrades count as new sales. Move a current client up a level (for example, from Accelerator to Scale) and it is treated as a new sale.
Existing clients are not commissionable. Brokers already working with Massimo stay with their current agreements unless you upgrade them.
What We Sell
CRE Scale: For established producers. 1:1 coaching plus weekly group calls.
CRE Accelerator: For mid-career brokers. Group coaching, 3 calls a week, 12-month term.
CRE Start: For new-to-business agents. Group program.
Massimo Membership: For brokers who want ongoing access. Self-serve membership.
You will sell all four. Your focus is the top of the ladder.
What You Own
Territory development
Build a target map of every broker, team, and brokerage in your territory.
Tier the map by production, team size, and fit for Scale, Accelerator, or Start.
Start with your highest-fit prospects. Expand from there.
Outbound and consults
Secure a minimum of 15 consults per week through your own outbound effort.
Respond to every prospect request from the Contact Us feature promptly.
Qualify and interview prospects quickly and honestly. If a prospect is not a fit, say so.
Closing
Run consults on Zoom and present the Massimo brand professionally (company virtual background provided).
Close Scale, Accelerator, Start, and Membership agreements.
Update the company database with accurate billing information as soon as an agreement is signed.
Strategic input
Tell the Sales Manager each week what is working and what needs to change in our systems and action plans.
Flag growth opportunities you hear from prospects, clients, and people in the industry.
Recommend ways to improve the client experience.
Track industry trends in coaching and training and report anything our clients could use.
Keep developing and sharing new sales material and ideas.
Targets
Year one: close a minimum of $2,000,000 in total contract value.
Reporting Rhythm
Daily: Schedule of the day's consults and detailed notes plus next steps for each consult in GoHighLevel. Daily sales briefing with the team on Zoom. Update GoHighLevel activity and the Scorecard Google Sheet.
Weekly: A 1-page summary report to the Sales Manager every Friday afternoon: activity, wins, challenges. Weekly check-in with the Sales Manager on systems and action plans.
Ongoing: Participate in standing team conference calls and company training. Keep your availability current in company systems.
Everything lives in the system. If it is not in GoHighLevel, it did not happen.
Compensation
Attractive commission rate based on actual closings, with a target of overall earnings of six figures plus in year one.
Who You Are
You have
A track record in B2B or high-ticket consultative sales. Coaching, training, SaaS, financial services, or commercial real estate experience is a plus.
Comfort selling five-figure and mid-five-figure programs to sophisticated buyers.
A working knowledge of how CRE brokers earn, or the curiosity to learn it fast.
Discipline. You prospect on days you do not feel like it.
Command of GoHighLevel, Zoom, and Gmail, or the willingness to master them in your first two weeks.
You are
Coachable. You take feedback and apply it by Friday.
Methodical. You use our proven sales framework and process, then add your own voice.
Honest. You will tell a prospect no when they are not a fit, even when it costs you a commission.
Likable and authentic. Brokers trust people who sound like peers.
In it for the long run. You want to build a book of business over years, not months.
Who Should Not Apply
Anyone who needs a base salary.
Anyone looking for a short-term stopgap.
Anyone who resists process or reporting.
Anyone who believes they have nothing left to learn.

Work arrangement
Yes