Remote Outbound Caller

PART-TIME OUTBOUND CALLER / QUALIFY PROSPECTS

Upkeep Standard is a family-owned residential cleaning company serving Northwest Chicagoland. We provide dependable biweekly and monthly home cleaning services.

We are hiring a reliable, confident, and coachable outbound caller to contact prospective customers, create interest in our services, qualify opportunities, and complete accurate follow-up.

This is a remote, part-time independent contractor position.

SCHEDULE

Monday - Friday
10:00 a.m.–2:00 p.m. U.S. Central Time
20 hours per week

Additional hours may become available based on performance, reliability, and business needs.

COMPENSATION

$5 per hour

Plus a $25 bonus for each new recurring biweekly or monthly customer who completes their first cleaning appointment.

RESPONSIBILITIES

* Make outbound calls using company-approved lead lists.
* Follow up with warm leads and previous contacts.
* Explain Upkeep Standard’s recurring cleaning services clearly.
* Ask qualification questions and identify interested homeowners.
* Invite qualified prospects to request a personalized quote.
* Leave clear, professional voicemails with the correct callback number.
* Send approved follow-up emails or text messages when instructed.
* Accurately record every call, disposition, note, and follow-up date.
* Prioritize scheduled callbacks and follow-up tasks.
* Create complete handoffs for qualified quote opportunities.
* Immediately document and honor all do-not-call requests.
* Remain logged into Microsoft Teams and available while clocked in.
* Participate in coaching, call reviews, assessments, and practice activities.
* Use only company-approved scripts, tools, pricing language, and processes.

The caller does not independently set prices, promise availability, offer discounts, negotiate rates, or guarantee services.

PERFORMANCE EXPECTATIONS

During a typical four-hour shift, the caller should work toward:

* 60–80 outbound calls
* Consistent follow-up on assigned leads
* Accurate documentation of all activity
* Professional and natural conversations
* Qualified quote opportunities, not unqualified names
* Complete and timely handoffs
* 100% compliance with do-not-call requests
* Reliable attendance and communication

Early performance will be measured primarily by qualified opportunities generated per 100 calls. Closed recurring customers and acquisition cost will be evaluated after the caller has completed the training and ramp-up period.

TRAINING AND RETENTION REQUIREMENTS

Training includes independent study, service and policy review, script practice, objection handling, mock calls, recorded practice, assessments, and supervised production.

To continue beyond training, the caller must:

* Complete all assigned training activities.
* Score at least 80% on the knowledge assessment.
* Demonstrate accurate knowledge of our services and policies.
* Complete mock calls with a passing score in at least four of five categories.
* Use the approved script naturally rather than reading mechanically.
* Correctly handle common objections and do-not-call requests.
* Enter complete notes and follow-up information.
* Demonstrate consistent attendance, communication, and coachability.
* Generate qualified interest during supervised calling.

Bringing in a new customer during training is encouraged but is not required to pass. Continued employment will be based on the behaviors and results the caller can control.

PROBATION AND REVIEWS

The position begins with a three-week probationary period.

Performance will be reviewed through weekly checkpoints, with a broader evaluation after six weeks. The evaluation will consider:

* Attendance and punctuality
* Call activity
* Conversation quality
* Qualified opportunities
* Follow-up completion
* CRM documentation
* Call-recording quality
* Coachability
* Policy compliance
* Recurring customers generated

Meeting the minimum standards does not guarantee additional hours. Strong and consistent performance may lead to expanded responsibilities and more hours. A longer-term performance review will also be completed after three months.

QUALIFICATIONS

* Previous outbound calling, appointment setting, telemarketing, customer service, or sales experience
* Clear and professional spoken English
* Strong listening and communication skills
* Ability to sound conversational rather than scripted
* Comfortable making repeated outbound calls
* Reliable availability during the scheduled Central Time hours
* Strong attention to detail
* Ability to accept coaching and apply feedback quickly
* Familiarity with CRM systems is helpful
* Experience with home services or business-to-consumer calling is a plus

EQUIPMENT REQUIREMENTS

Applicants must have:

* A dependable computer
* A quality headset
* Stable high-speed internet
* A quiet and professional workspace
* Reliable access to Microsoft Teams and other company systems

DATA AND COMPLIANCE

The caller must use only approved company systems and lead lists. Company or customer information may not be copied, exported, downloaded, or stored in personal systems.

Unauthorized cold texting, auto-dialing, prerecorded messages, ringless voicemail, or AI-generated voice calls are prohibited. Do-not-call requests must be honored immediately.

HOW TO APPLY

Step 1


Email a 60–90 second introduction video to ---------- the video, briefly introduce yourself and explain:

* Your outbound calling or customer service experience
* Why you are interested in this position
* Why you would be effective when speaking with homeowners

Step 2

Include the following information with your video:

* Your relevant experience
* Your availability during U.S. Central Time
* Your desired hourly rate
* Confirmation that you have a computer, headset, and stable internet
* Your résumé

Please do not submit a lengthy written introduction. We are primarily evaluating communication, reliability, relevant experience, and availability.