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Entry-Level Outside Sales — $3,900 Training Guarantee + $200 Per Appointment (No Experience Needed)

Trinity Roofing
Worcester, MA Full Time
POSTED ON 9/22/2026
AVAILABLE BEFORE 1/19/2027

Entry-Level Outside Sales — $3,900 Training Guarantee $200 Per Appointment (No Experience Needed)

You’ve got a competitive engine and nowhere at work to use it — most entry-level jobs pay you to stand still and pay the same whether you win or coast. This one pays you to compete, with $3,900 guaranteed under your training program so you can learn the game without betting rent on it. And we have every reason to coach you hard: our whole business depends on new people getting good. At Trinity Home Exteriors, our canvassing team works outdoors, sets appointments for our home specialists, and gets paid on performance — from the very first appointment, starting in training. This is not a closing sales role — no contracts, no pressure pitches. You talk with homeowners, find the ones who want a free inspection, and book the appointment. We teach you everything.

Straight up: this is a field-based, door-to-door role in assigned neighborhood territories — not remote, not an office. Full-time and part-time welcome as long as the 2-week training program is completed (Mon–Fri, 9am–4pm).

How the Pay Works — paid weekly, per appointment, in two parts, because we reward real appointments, not padded numbers:

  • $35 the moment your appointment is set and qualified
  • $165 more when the appointment happens — $200 total per completed appointment
  • 1% of the job when your appointment turns into a signed sale (roughly $150 on a typical roof)

The $3,900 Training Guarantee: your pay is guaranteed across the training program, paid weekly starting day one. Work your shifts, log your doors, and you're paid the guarantee.

Weekly Bonuses (they stack): 3 completed appointments: $100 · 6: $250 more · 9: $500 more ( $850 total that week) · first appointment by Tuesday: $25.

Monthly Consistency Bonus: 20 completed appointments each 4-week period: $400, growing $100 every period earned, up to $800.

Automatic Raise at 3 Months: Senior rates — $225 per completed appointment, 1.25% on sold jobs. Automatic, not negotiated.

What you can earn: 3-appointment weeks ≈ $700 · 9-appointment weeks ≈ $2,675 — before sold-job pay and consistency bonuses. Consistent performers pace $95,000 year one.

Schedule: Monday–Friday 3:00–8:00 PM · every Saturday 11:00 AM–6:00 PM · Sunday off. When clocks fall back each autumn, weekday hours shift to 11:00 AM–6:00 PM until spring — we knock the hours homeowners actually answer.
Company Location: 435 Lancaster Street, Leominster, MA 01453 · Full-Time · Roofing, Home Improvement, Canvassing

W2 position — taxes withheld, workers’ comp covered, weekly pay every Sunday · health insurance and optional 401(k) with company match — eligible at 90 days.

What the Job Is Like: working outdoors and staying active · a live leaderboard with clear performance tracking · milestones announced out loud · friendly competition on a tight-knit team · owners who know your name.

Training Program (2 Weeks) — You Earn From Day One: the guarantee covers training, and every qualified appointment you set during training pays full rates on top. Fundamentals, canvassing strategy, confidence at the door, objection handling, territory planning — at real doors, alongside the team.

Career Growth — We Promote From the Doors: Canvasser → Senior Canvasser (automatic at 3 months) → Mentor ($40 override on every trainee appointment) → Senior Mentor → Customer Development Director. Every leader here started at a door.

Qualifications: competitive, team-oriented mindset · strong communicator · reliable and consistent · coachable · comfortable outdoors · evenings and Saturdays. Competitors do well here — former athletes, team-sport people, anyone who keeps score. Never sold anything? Good — we’d rather build a competitor from scratch than untrain bad habits. Show up and stay coachable, and we work on your game with you until you win — that’s the program, in writing.

About Trinity Home Exteriors: family-owned, 17 years across Massachusetts and New Hampshire — built on trust, professionalism, and long-term relationships. Apply today.
Benefits: Weekly pay · $3,900 training guarantee · Performance bonuses · Work Location: In person

Pay: $72,000.00 - $130,000.00 per year

Benefits:

  • 401(k)
  • Dental insurance
  • Health insurance
  • Paid training

Work Location: In person

Salary : $72,000 - $130,000

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