Outreach Field Sales Rep (Central IL & Chicago South Suburbs)

This is a field sales role with a mission. You'll travel your territory daily, walk into facilities cold, build relationships from scratch, and guide people through a program that genuinely changes their lives. If you're a self-starter with a proven sales track record who wants their work to mean something — read on.

About the Role

Every day, seniors and people with disabilities across Illinois go without the equipment they need to communicate — simply because they don't know there are options available to them, at no cost. You could change that.

Our Outreach Field Sales Representatives travel throughout their assigned territory to educate seniors and people with disabilities about a communication equipment program available to them — a state-funded initiative that provides free assistive equipment to qualifying Illinois residents.

This is a relationship-driven, mission-focused role — but it requires the instincts and discipline of an experienced field sales professional. You'll be managing your own territory, building a pipeline of facilities and contacts, and driving consistent program growth through outreach, presentations, and follow-through. Many of our reps say the best part of the job is the moment someone realizes help is available to them — and that you were the one who told them.

Your Territory

This posting covers a territory spanning the southern Chicago suburbs and outer metro area — including the Orland Park-Homewood-Chicago Heights area, as well as the Joliet and Kankakee corridors — extending south through Champaign-Urbana, Bloomington/Normal, Pontiac, and west to Peoria. We refer to this territory as Chicagoland South / Central IL. Candidates should be centrally located within this region and comfortable with regular driving across a wide geographic area.

Occasional travel to other regions may be required for training or special events.

What You'll Do

Build and Manage Your Territory

• Travel throughout the territory regularly to establish and maintain relationships with activity directors, facility coordinators, and community organizations
• Cold call and visit new facilities to introduce the program and book outreach events
• Serve as the face of the program — professional, personable, and knowledgeable
• Represent the program at community events, senior living facilities, expos, and educational sessions

Drive Program Outcomes

• Guide interested individuals through the application process and complete on-site follow-up as needed
• Maintain a consistent pipeline of booked events and follow through reliably on scheduled commitments
• Work toward consistent monthly application growth as your territory develops and relationships deepen
• Log all outreach activity accurately and consistently in our CRM
• Communicate regularly with our support team via email, Zoom, and phone, including weekly updates

What We're Looking For

Required:

• Proven background in field sales, outside sales, or territory management — you know how to open doors, build rapport, and move people toward a decision without relying on high-pressure tactics
• Comfortable working independently and managing your own schedule without close supervision
• Comfortable leading group presentations and one-on-one conversations with seniors and people with disabilities
• Reliable personal vehicle, valid driver's license, and comfort with extended daily driving across multiple days per week
• Strong communication, organization, and follow-through — you do what you say you're going to do

Preferred:

• Familiarity with assistive technology, disability services, or state-funded programs
• Comfort navigating both rural and suburban communities across a wide territory
• Experience building referral relationships with healthcare, senior living, or social service contacts
• Experience in senior living environments (activities coordination, resident engagement, family communication) — a plus, but secondary to a strong sales background

You're a Great Fit If...

You have a proven track record in field or outside sales — you've managed a territory, worked independently, and know how to walk into a cold environment and walk out with results. You're self-motivated, disciplined, and don't need someone managing your day-to-day to stay productive. You're energized by the challenge of building something from the ground up and find genuine satisfaction in helping people access services they didn't know existed. Equally important — you know how to guide people toward a decision without being pushy or aggressive. You earn trust, you don't pressure it.

If you also have experience in senior living — activities coordination, resident engagement, or family services — that's a real bonus. Familiarity with that world makes the relationship-building side of this role even more natural. But it's the sales foundation that matters most.

Performance Expectations

This is not a commission-based role — compensation is a fixed pay rate (paid biweekly), with no commissions tied to individual application counts or events. That said, this role does carry clear performance expectations and we do reward proven performers. Representatives who prove themselves in the field — consistent results, strong territory management, and reliability — can expect that to be recognized through compensation reviews and rate increases.

Deliverables include:

• Events booked and completed (facility presentations, community expos, educational sessions)
• Demonstrated month-over-month growth in program applications within your territory
• Consistent and accurate activity logging in our CRM
• Regular communication with the support team, including weekly updates

What to Expect in the First 90 Days

We provide hands-on onboarding both in the field and with our support team. Over your first 90 days, you will:

• Complete onboarding training and accompany an experienced rep in the field
• Begin independently managing your region and building your facility contact list
• Establish a consistent weekly outreach rhythm with measurable engagement activity
• Develop familiarity with our CRM and reporting processes

Eligibility & Contract Terms

Because this role involves seniors, people with disabilities, facilities, and regular travel, all applicants must:

• Have a valid driver's license and reliable personal vehicle with valid insurance
• Pass all required background checks and drug screenings
• Be able to transport and set up materials for presentations and events (ability to lift up to 40 lbs.)

This is a 1099 independent contractor position and does not include employee benefits, a vehicle, or routine mileage/travel reimbursement**. Regular travel within the assigned territory is expected and is the responsibility of the contractor. The territory extends up to approximately 2 to 2.5 hours one-way from the candidate's home base — not every day reaches that range, but comfort with some longer drives is a must.

**For out-of-region assignments (e.g., overnights), travel reimbursement will be provided (e.g., hotels, car rental, meals). These out-of-region trips are infrequent and coordinated with you well in advance.

The schedule is primarily Monday–Friday during daytime hours. Occasional evening or weekend events may arise and are coordinated in advance with the management team.

Ready to Make a Difference?

If you're energized by meaningful work, thrive in an independent field role, and want a position where your effort directly drives results — we'd love to hear from you. Please submit your resume and a brief note about why this role interests you.

We review applications on a rolling basis and aim to respond within one week.