Outerland Holdings, LLC
Landscape Maintenance Estimator
Mashpee, MA
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hirly's read of this role
- Seniority
- Mid level
- Stated salary
- $75,000 – $100,000 per year
- Country
- US
- Work mode
- On-site / unstated
- First seen by hirly
- 3 Nov 2026
Derived automatically from the posting. Upload your resume above to see how the role scores against it.
the posting
Description
As the Landscape Maintenance Estimator, you’ll be a prospective client’s first experience with Outerland, and the person who earns their business. The estimator role blends consulting, sales, horticultural problem-solving and customer service: you’ll read a property, understand what the client values, design a maintenance plan that fits their landscape and their goals, and hand off a relationship our account managers are excited to inherit. New clients will walk away with the impression that we communicate, we care, and they’re a big deal to us.
Requirements
Own inbound leads from first handshake to signed proposal, with follow-up that never leaves anyone wondering
Walk properties with prospective clients — listen to their priorities, assess conditions, and communicate our value
Build tailored maintenance plans around site conditions, takeoffs, client goals, company service offerings, and real budgets
Put together accurate, detailed estimates and present proposals you can stand behind
Lead the initial client meeting, set clear expectations, answer the follow-up questions, and close the sale
Onboard new clients and hand off cleanly to their account manager — site notes, scope, and preferences all in one place
Catch enhancement and upsell opportunities during site visits and pass them to the account management team
Accurately, consistently, and proactively manage the sales pipeline within our CRM
Track and manage sales performance against the sales budget
Qualifications
3+ years in sales or account management. Landscaping or green industry experience is preferred, but not required
A working knowledge of landscape maintenance, plant material, and the problems properties tend to have — or the drive to learn it fast
A consultative style: you ask good questions, listen more than you pitch, and communicate our value clearly to clients.
Self-direction, ruthless attention to detail, and exceptional organizational skills
Compensation & Benefits
$75,000 – $100,000 base salary based on experience
Performance-based bonus opportunity
Company vehicle, phone, and laptop
Health, dental, vision, and supplemental insurance
401(k) with company match
Listed on hirly, a job board. hirly is not the employer: Outerland Holdings, LLC is hiring for this role.
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