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 ForHunger > 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–$80kOTE: $200k+Benefits: Health, dental, vision, 401(k)
  • Hit your numbers → promotion path in 2–6 months (AE/AM/Ops/Leadership)
  • Interview Process1 screening call → work trial → decision within 72 hours.
  • We move fast. No slow hiring cycles.

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Level

Senior L5

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$60k–$80k

Location

Chicago, IL

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Industry

Insurance Agencies and Brokerages

Posted

9 days ago

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