Want to break into tech sales at a YC-backed startup?

Beagle is hiring early-career reps who want to move fast, learn fast, and grow into leadership.

We are hiring for our Chicago office (on-site).

About the Role

Beagle is building the first fully automated insurance carrier. We’re hiring hard-working, high-energy early-career sales reps to join our in-person team in Chicago.

This is a ground-floor sales role where you’ll learn outbound, talk to property managers daily, and move fast.

You’ll be working with a product used by property managers, powered by AI, in a $1T+ market

Schedule:

Monday–Friday: 7:30 AM – 6:00 PM (in-office)

Once a month training on Saturday: 12 PM – 1 PM (in-office)

What You’ll Do

Make outbound calls + book meetings with property managers

Keep CRM updated daily

Help accounts from deal-close → onboarding → billing

Clear blockers fast during onboarding

Spot upsell opportunities

Be in-office 5-6 days/week (AE path)

What We Look For

Hunger > experience

Confident communicator

Comfortable talking with customers

Thrives in high-speed, high-accountability roles

Strong organization + follow-through

Must be authorized to work in the US.

Compensation

Base: $60k–$80k

OTE: $200k+

Benefits: Health, dental, vision, 401(k)

Hit your numbers → promotion path in 2–6 months (AE/AM/Ops/Leadership)

Interview Process

1 screening call → work trial → decision within 72 hours.

We move fast- no slow hiring cycles