"Sales Manager — Real Estate Vertical"

Cloudstaff

Location: Brisbane preferred, or Eastern Seaboard (2–3 days per week in office), national remit. Frequent domestic travel plus periodic travel to the Philippines.

 

Compensation: Base AUD 130,000–160,000, with flexibility to AUD 180,000 for the right candidate. OTE approximately AUD 220,000–230,000 in year one, rising 30–40% in year two as trailing commissions compound.

 

Other headline inclusions:

 

Recurring commission — 6% of monthly client fee per seat in year one, rising to up to 11% per seat in year two where a client grows to five or more seats, paid on a trailing basis for up to 24 months. Superannuation, per-kilometre travel reimbursement and a corporate card for client entertainment. President's Club programme planned for mid-next year. No healthcare provided.

 

Summary:

 

A genuine player-coach role leading Cloudstaff's Australian real estate vertical. You inherit a patch of 50–60 existing accounts already buying seats, hunt net-new across the national market, and coach a team of three reps who are currently under-supported. You carry your own number alongside team responsibility. The vertical is targeted to grow from roughly 500 to 1,300+ seats within twelve months, backed by significant marketing investment and warm relationships with major franchise groups including Ray White.

The Company

Cloudstaff is a technology-enabled offshore staffing business — a hybrid of the Employer of Record and BPO models. It recruits, employs and supports offshore staff, primarily in the Philippines, handling payroll, compliance, systems, facilities and HR while clients direct the day-to-day work. It was founded by a technologist, which is why the business runs on a proprietary client platform rather than a traditional labour-broking model.

 

Today Cloudstaff has around 8,000 staff globally and roughly 780 clients, with about 300 in the US. Australia is its most mature market, and real estate is a flagship vertical at 450–500 seats. The business is private equity backed by Ares Management, who take an active role in senior hiring.

 

Internally the company invests heavily in its people — company events run at 30,000–35,000 attendees including staff families, AI training has been rolled out to more than 2,500 employees, and its proprietary recruitment platform has processed over 1.4 million applicants. Leadership describes the business as operating at startup pace despite its size.

The Role

This role exists because the vertical is underperforming against a very large opportunity. The current lead is a capable individual seller but has not been able to build a team around him — reps were hired to protect his position rather than for performance, and the team has had little training, structure or accountability. Targets are being missed despite abundant market demand.

 

You would run three lanes at once:

 

Individual contributor. You take on a defined patch of 50–60 existing accounts already purchasing seats, and grow them. Land-and-expand is the core motion — clients typically start with one or two seats and scale from there, and retention strengthens materially once an account reaches five or more.

 

Hunter. You self-source net-new business across the national real estate market. Client-stated TAM sits at roughly 15,000 real estate agents and 30,000 offices nationally; Ray White alone is estimated at around 3,000 potential seats that the group itself is largely unaware of.

 

Coach. You mentor and develop the three existing reps and the incumbent lead — training, honest feedback, accountability. This is not a supervisory role. The client is explicit that they want someone who can give tough feedback well and lift performance, not someone who manages activity reports.

 

Alongside this you represent Cloudstaff externally: industry events, keynote speaking, and boardroom conversations with franchise principals. Team target is around 110 seats per month, roughly 30 per rep.

 

You are supported by a centralised APAC marketing team based in Melbourne that runs campaigns and staffs event booths, so your time goes into selling rather than marketing execution. The stack is HubSpot, Microsoft and Power BI.

What Success Looks Like

• First 30 days: Understand the offshoring model in depth, including time on the ground in the Philippines. Map the 50–60 account patch and identify the strongest expansion candidates. Assess each of the three reps individually — capability, gaps, motivation — and build a working relationship with the incumbent lead.
• First 60 days: Personal pipeline live and building. A coaching and training cadence in place with the team. Clear view of which accounts expand fastest and where the net-new focus should sit. Early relationship-building underway with major franchise groups.
• First 90+ days: Consistently hitting your own number while team performance measurably lifts toward the 110 seats/month target. Structure, accountability and training rhythm established. Representing Cloudstaff credibly at industry events and in franchise boardrooms.
• 12-24 months perspective: Vertical scaled toward 1,300+ seats. Team grown beyond the current three reps, with your own hiring bar applied. NSW coverage gap closed. The vertical operating as a professionalised, repeatable engine rather than a collection of individual sellers.

What You'll Bring

Must-haves:

 

• An active, current closing track record — you are still selling personally, not managing from a distance
• Demonstrable experience coaching and developing junior sellers, including giving difficult feedback well
• Background in PropTech, SaaS sold into real estate, or property management leadership. Real estate operators who have genuinely run a team are also in scope
• Proven land-and-expand account growth, not hunting alone
• Executive presence — credible in a boardroom with franchise principals, and comfortable on a stage
• High autonomy and self-management; this hiring manager does not micromanage
• Stable tenure, generally two-plus years per role

 

Nice-to-haves:

 

• HubSpot proficiency and strong pipeline discipline
• Existing relationships across Australian real estate franchise networks
• NSW network or coverage capability, given the current team gap
• Prior exposure to offshoring, BPO or EOR models

Why This Role

Most sales leadership roles ask you to choose between selling and leading. This one deliberately doesn't — you keep your own number and your own accounts while building a team, which suits operators who don't want to hand over the tools. You inherit warm accounts rather than a cold patch, and the commission structure has a 24-month trailing tail, so what you build compounds rather than resetting each January.

 

The market position is genuinely strong. Cloudstaff is already one of the largest offshoring providers in Australian real estate, and the gap between current seats and realistic addressable seats is very wide. The marketing budget is committed and the central team executes it, so your time goes into revenue rather than booth duty.

Why We're Excited About This One

The problem here is well-diagnosed and honestly stated, which is rare. Leadership knows exactly why the vertical is underperforming — poor hiring, no training, a lead who protected his own position — and is not pretending otherwise. That makes this a genuine build rather than a rescue with hidden politics.

 

The PE backing from Ares Management matters too. It brings capital, discipline and board-level exposure, and it signals that the growth target is funded rather than aspirational. For someone who wants a vertical they can put their name on, the runway is real.

Hiring Process

1. Matthew Rutter and Allison — first round
2. CEO and CFO — strategic round
3. Ares Management — private equity partner validation
4. Go-to-market plan or 30/60/90-day presentation may be requested at later stages

 

FAQ's

 

TBC — to be populated once Matthew Rutter confirms outstanding detail on quota ramp, onboarding structure, equity, leave policy and the personal quota figure for this role.