Corgi Insurance

Make high-volume outbound calls to qualify leads and book meetings for Account Executives in a structured sales environment. | Experience in high-volume outbound prospecting, lead qualification, and CRM usage with a hunger for sales career growth. | 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 Screening call Work trial with live cold calls Onsite with the team Decision, fast If you read this and felt ready to pick up the phone, apply. We move quickly, and so should you.

Manage client onboarding, success, and operational accuracy to ensure customer satisfaction and data integrity. | 2-5 years in customer success or operations with strong technical aptitude and excellent communication skills. | About Beagle (a Corgi Company) At Beagle, we are rebuilding the insurance industry from the ground up, starting with renters insurance for property managers and multifamily portfolios. We are part of Corgi, a YC-backed startup, launching our Dallas and Chicago offices from scratch to scale our renters-insurance programs nationwide. We are looking for a Customer Success Manager (CSM) who can bridge operational accuracy with client relationship excellence. This is a hybrid role combining data integrity, onboarding, and customer experience, ensuring every property manager thrives using Beagle’s platform. What You Will Do As a Beagle Customer Success Manager, you will be the trusted partner guiding our clients from onboarding to long-term success. You will ensure every property manager we serve gets maximum value out of Beagle’s products and services. Your role is to retain, educate, and support, driving satisfaction and seamless adoption across every account you touch. Client Management & Success Serve as the main point of contact for assigned clients from onboarding through renewal. Lead new client launches, ensuring accurate program setup and smooth adoption. Monitor account health and provide proactive guidance to optimize performance. Conduct regular business reviews with clients to assess satisfaction and identify growth opportunities. Resolve client issues efficiently by collaborating with Sales, Product, and Operations. Operational Accuracy & Reporting Configure and validate reports across property management systems (e.g., rent rolls, billing, compliance). Ensure accuracy of key metrics (ARR, OR, unit counts, compliance %) within the Insurance Operating System (IOS). Maintain consistent GL code mappings, charge types, and billing structures. Cross-check and audit data regularly to prevent errors, discrepancies, or compliance drift. Provide dashboards and insights to leadership for portfolio performance tracking. Process Improvement & Training Develop playbooks and SOPs for onboarding, validation, and troubleshooting. Train internal teams (AEs, AMs, and CS) on key system workflows. Collaborate with Product and Risk to identify gaps and surface operational improvements. • Standardize processes to improve reporting and prevent workflow breakdowns. What We Are Looking For 2-5 years of experience in Customer Success, Operations, or Implementation (preferably SaaS, proptech, or insurance). Strong technical aptitude with systems such as Yardi, AppFolio, Entrata, or similar property management software. Excellent attention to detail and data integrity skills. Confident communicator who can explain technical issues to non-technical stakeholders. Process-driven, proactive, and organized with strong ownership over client success. Comfortable working in-person, 6 days per week in a fast-paced startup environment. Compensation and Growth Path Base Salary: $70,000-$90,000 (based on experience) On-Target Earnings (OTE): $90,000-$120,000 with quarterly performance bonuses Performance Bonuses: Based on client retention, satisfaction (CSAT/NPS), and data accuracy KPIs Career Growth: Clear pathway to Senior CSM, Implementation Manager, or Account Manager roles based on performance Note: This role does not include equity. Compensation is structured for strong base stability with meaningful performance upside. Why Join Beagle Ground-Floor Impact: Help shape how Beagle delivers success to its growing client base. Cross-Functional Exposure: Work directly with Sales, Product, and Risk teams. Mission with Momentum: Be part of a team redefining insurance with data accuracy and integrity. Career Acceleration: Top performers grow quickly into leadership or commercial-facing roles. Operational Excellence Culture: Every process you improve scales nationally. In-person only. Full-time. No remote options. If you are ready to combine customer success with operational precision, this is your opportunity to help shape the foundation of Beagle’s client experience. Apply now and join us in rebuilding insurance from the ground up.

Lead full talent lifecycle including recruiting, retention, and people operations. | Requires 3+ years building people function at startup and proficiency with recruiting tools. | About Corgi Corgi is a full-stack insurance carrier building better, faster insurance products for startups. We’re not a broker, so we underwrite and issue policies directly, with fewer handoffs and less friction. Cutting out intermediaries lets us tailor coverage to how companies actually operate and price risk more efficiently. About the role We've raised over $108M to build insurance from the ground up. Now we're building the team that builds the team. This is our first dedicated People hire. You'll own everything from how we find talent to how we retain it. Think recruiting, people ops, culture, comp, and everything in between. This isn't a "post jobs and review inbound" seat. We need someone who moves fast, builds from scratch, and has a hunter mentality. What you'll do Own full-cycle recruiting across all functions: sourcing, closing, and everything in between Stand up repeatable hiring playbooks by role and team Build and run core people ops: HRIS, payroll, onboarding, compliance Design comp frameworks, leveling, and performance processes as we scale Shape culture intentionally… not with perks, but with systems and standards Partner directly with leadership on headcount planning and org design What we're looking for 3+ years of experience building a people function from scratch at a high-growth startup Strong sourcing chops, going beyond LinkedIn and close competitive candidates creatively Hands-on with modern recruiting tools and ATS platforms (we currently use Ashby) Equally comfortable in the weeds of people ops and thinking strategically about org health High ownership and scrappy – you build the plane while flying it! Bonus Experience hiring enterprise or technical talent Background in tech or SaaS sales Familiarity with insurance or financial services Why join Get in early at a company that's already won with $108M raise Direct line to leadership and real influence over how we grow You're not inheriting someone else's playbook — you're writing it Compensation Base: $160,000-$230,000 Equity: included Interview Process Screening Call Work Trial Decision