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Sales Development RepresentativeCorgi Insurance Services, Inc • Boston, Massachusetts, United States
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Sales Development Representative

Corgi Insurance Services, Inc
  • US
    Boston, Massachusetts, United States
  • US
    Boston, Massachusetts, United States
Apply Now

About

Sales Development Representative

Trucking Insurance San Francisco On-site

Early-career outbound sales. A path to Account Executive in 12 months. $150K+ on-target earnings.

Corgi is building a fully automated insurance carrier, and we just earned approval to sell trucking insurance nationwide. The market is worth more than $40 billion, and almost all of it still runs on paper files and rating engines built in the 1990s. We are rebuilding it from scratch.

This is your chance to get on the phones at the very start, learn outbound sales from the people building the company, and earn your way to Account Executive faster than you could anywhere else.

The Role

You will spend your days calling fleet owners, dispatchers, and safety directors, qualifying them, and booking meetings for our Account Executives. You will research every account before you dial, run a disciplined call cadence, and keep your pipeline clean. This is high-volume, high-accountability outbound sales. It is demanding, it is measured daily, and it is the best sales training ground we know of.

We hire for hunger, not pedigree. Hit your numbers and you move up to Account Executive within 6 to 12 months.

This role is on-site in San Francisco, 5 to 6 days a week. It is not remote and it is not hybrid. We win in the building, together.

What Success Looks Like

Your first week

  • Get certified on our product, our underwriting appetite, and how trucking insurance actually works, so you can hold a real conversation with a fleet owner
  • Build your target account list and your call cadence
  • Make your first 100+ dials

Your first month

  • Hit 100+ dials and 30+ emails a day, every day
  • Book qualified meetings your Account Executive can close
  • Hand off every meeting clean, with the fleet size, equipment, lanes, and loss history already researched

Months three to six

  • Consistently hit your meeting and pipeline targets
  • Support accounts from close through first bind, clearing blockers fast
  • Earn your promotion to Account Executive
Who Thrives Here

You will do well here if you are hungry, competitive, and want to outwork everyone around you. You are comfortable picking up the phone and hearing no fifty times to get to a yes. You are organized, you follow through, and you do what you say you will do. You want a sales career, and you want it fast.

It helps if you have a competitive background in athletics, the military, debate, or sales, any prior outbound experience such as SDR, door-to-door, fundraising, or recruiting, or genuine curiosity about trucking, logistics, and insurance. None of it is required.

You must be authorized to work in the United States.

Who You'll Work With

You will report directly to the two leaders building this division.

Brianna Lynch, Head of Finance. Brianna began her career at EY, then led FP&A and Corporate Development at HarbourVest Partners before moving to Affiliated Managers Group, an $880 billion asset manager, where she worked on M&A and Investor Relations across private equity, hedge fund, and venture capital firms. She joined Corgi in 2025 and leads M&A alongside Drew.

Drew Bregman. Drew founded a behavioral assessment company that helps the NSA and the U.S. military identify talent. He co-founded Corgi's M&A team and built the sales division at our subsidiary Beagle, where revenue grew 40% month over month. He started his career building transportation management software for a large freight brokerage.

Compensation
  • $70,000 to $90,000 base salary, based on experience
  • $150,000+ on-target earnings
  • Full health, dental, and vision coverage
  • A clear, fast path to Account Executive
How to Apply
  1. Screening call
  2. Work trial with live cold calls
  3. Onsite with the team
  4. Decision, fast

If you read this and felt ready to pick up the phone, apply. We move quickly, and so should you.

  • Boston, Massachusetts, United States

Languages

  • English
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