Job Details

Caddie is hiring on behalf of a fast-growing, mission-driven marketplace company.

This company exists to lift as many people up the socioeconomic ladder as possible. They dramatically improve lives by enabling professionals to turn extra time and ambition into career growth and financial opportunity. They achieve this through an app-based marketplace that connects workplaces and professionals, allowing professionals to book on-demand shifts and workplaces to access on-demand talent.

About the Company:

Our client is a fast-growing Series C marketplace and a leader in the Long Term Care vertical, with expansion underway into additional verticals including Dental Offices and Schools.

They are a YC Top Company with a global, remote team of 700+ employees. The company has been profitable since 2022 and fills millions of shifts annually at partner workplaces across the US, where tens of thousands of professionals work through the platform each year.

They are looking for top talent to help continue scaling and serving more professionals and workplaces nationwide.

Salary Range

$80,000 - $120,000 USD per year

About the Role

Our client is transforming the talent marketplace by connecting workplaces with the professionals they need, when they need them.

Their Sales team is growing quickly and doing meaningful, high-impact work in a fast-paced, performance-driven environment.

As a Territory Account Executive, you'll act as the “Sales CEO” of your territory: prospecting, closing, and expanding facility partners through in-person selling, while owning revenue growth in your assigned market(s).

They are hiring for two types of Territory Account Executive roles:

• Local Territory AE (In-Market)

Eligible if you live in one of the company's core priority metros (listed below)

Field time: 3–4 days each week

Territory: one core metro — your local area

Core Priority Metros:

Pacific:

San Francisco Bay Area, CA

Los Angeles - Long Beach - Anaheim, CA

Portland - Vancouver - Hillsboro, OR-WA

Central:

St Louis, MO-IL

Chicago - Naperville - Elgin, IL-IN-WI

Cleveland - Elyria, OH

Cincinnati, OH-KY-IN

Eastern:

Atlanta - Sandy Springs - Alpharetta, GA

Newark - Jersey City, NJ

New York, NY

Nashville - Davidson - Murfreesboro - Franklin, TN

Philadelphia - Camden - Wilmington, PA-NJ-DE-MD

Baltimore - Washington, DC-VA-MD-WV

Pittsburgh, PA

• GTM Territory AE (US-Based, ~50% Travel)

Eligible if you live anywhere in the US

Field time: ~50% travel; 1–2 week blitzes at a time (requiring overnight stays)

Territory: cluster of smaller metros, often within the same region

In both cases, you will be the face of the company in your markets, spending significant time in the field meeting with and winning over decision makers at long term care facilities. This is an opportunity to own markets from the ground up. Whether you're early in your career and eager to build quickly, or an experienced seller/operator ready to lead territory strategy and execution, this role offers significant ownership and growth potential.

What You'll Do

• Prospect, pitch, and close new healthcare facility partners through field sales and local business development
• Manage and grow relationships with existing customers to deepen engagement
• Conduct in-person meetings, demos, and site visits across your territory
• Develop a deep understanding of your local healthcare landscape and competitors
• Partner with internal teams to deliver an excellent customer experience
• Maintain clear pipeline and activity tracking in CRM (B2B Sales Environment)
• Spend 4 days per week in the field meeting with customers and prospects

Who You Are

• As mentioned above, the team is growing rapidly and hiring both early-career and experienced professionals across most markets. Below outlines what they're looking for in both profiles.
• Early Career Path
• 0–2 years of experience in sales, account management, customer-facing roles, or B2B field sales
• Fast learner who thrives in dynamic environments and wants to build a strong commercial foundation
• Motivated by fieldwork and relationship building
• Eager to grow into territory ownership and leadership as markets scale
• Experienced Path
• 3–5+ years of experience as territory manager, outside sales rep, business development, or account manager (healthcare or marketplace experience a plus)
• Skilled at managing a full book of business — prospecting, closing, and expanding existing accounts
• Data-driven and strategic, able to shape territory plans and mentor newer teammates
• Comfortable owning results end to end with minimal oversight

What You Bring (All Candidates)

• Strong communication and relationship-building skills across clinical and business audiences
• Curiosity, persistence, and a bias for action
• Organization and autonomy in managing your own schedule and pipeline
• A reliable vehicle, valid driver's license, and ability to travel (either locally or overnight, depending on whether you're applying for the Local Territory AE or GTM Territory AE role)

What They Offer

• Competitive base salary + uncapped commission
• Insurance benefits and 401k options
• Unlimited PTO and flexible holidays
• Mileage reimbursement or travel stipend for field work
• Remote flexibility when not in the field
• Clear growth path into Territory Manager, Senior Account Executive, or Sales Management roles