Insurance Sales Representative

🧡📦💙Founded in 2012, EasyPost is a YC unicorn whose mission is to make shipping simple for businesses—from garage startups to the Fortune 500. Shipping, now more than ever, is the backbone of the global economy, but integrating the technology-enabled operations of a modern business with the low-tech and complex shipping industry has always been a challenge. EasyPost solves this problem with the first developer-friendly REST API for shipping, and we continue to push boundaries and discover new ways to simplify shipping for all. Our team is rapidly growing, and this is the perfect time to get on board. Join us and help build the shipping infrastructure of the future. We’re builders, problem-solvers, and “there has to be a better way” people. We like elegant architecture, fast decisions, and shipping (pun intended) improvements that power millions of deliveries every day. We stay scrappy, we move fast, and we don’t wait for permission to innovate in an industry that desperately needs it. If you want to work on systems that actually move the world—literally—you’re in the right place. 🚚✨   EasyPost does not consider candidates who misrepresent their identity, experience, employment history, or technical qualifications. Applications containing false information, stolen professional profiles, or unverifiable credentials will be removed from consideration. We conduct early-stage verification of resumes, LinkedIn profiles, GitHub accounts, and other relevant professional information as part of our hiring process.

Position Summary

The Parcel Insurance Account Executive will be responsible for driving new business, revenue growth, and customer adoption within the company’s Parcel Insurance business. This is a quota-carrying sales role focused on building relationships with prospective customers, understanding their shipping and risk-management needs, and positioning insurance solutions that protect their shipments while creating measurable value for their business.

This is a newly created position and an opportunity to play a foundational role in growing the Parcel Insurance business. The ideal candidate brings a strong understanding of parcel or freight insurance, a proven track record of consultative B2B sales, and the ability to build relationships with decision-makers across e-commerce, logistics, shipping, and related industries.

The Account Executive will work closely with Sales, Product, and Insurance leadership to develop and execute sales strategies, build a healthy pipeline, close new business, and help shape how the company approaches the Parcel Insurance market.

Essential Duties & Responsibilities

o Own a sales quota and consistently achieve or exceed revenue and new-business targets.

o Develop and execute a territory and account strategy focused on acquiring new Parcel Insurance customers.

o Identify, prospect, and engage high-potential accounts within target industries and market segments.

o Build and maintain strong relationships with decision-makers and key influencers across prospective and existing accounts.

o Serve as a trusted advisor to customers by understanding their shipping volumes, loss exposure, insurance requirements, and broader business objectives.

o Conduct account research and discovery to identify customer pain points, insurance gaps, and opportunities for improved shipment protection.

o Clearly communicate the value proposition, capabilities, and competitive advantages of the company’s Parcel Insurance solutions.

o Lead sales presentations, product demonstrations, discovery meetings, and commercial conversations with prospective customers.

o Develop and maintain a strong, accurate sales pipeline through proactive outbound prospecting, networking, referrals, and inbound opportunities.

o Manage the full sales cycle from prospecting and qualification through negotiation, close, and handoff.

o Negotiate pricing, contracts, and commercial terms while balancing customer needs with company objectives.

o Partner closely with internal Sales, Product, Operations, and Insurance teams to ensure a seamless customer experience and successful implementation.

o Maintain accurate account, opportunity, activity, and forecast information within Salesforce or other CRM systems.

o Monitor market trends, competitor activity, and customer needs to identify new opportunities for growth.

o Provide feedback to Insurance and Product leadership to help inform product strategy, positioning, and go-to-market initiatives.

o Build long-term customer relationships and identify opportunities to expand insurance adoption within existing accounts.

o Stay current on parcel insurance products, market dynamics, regulations, and competitive offerings.

Minimum Qualifications

o High school diploma or equivalent required; bachelor’s degree preferred.

o 5+ years of B2B sales experience, with a demonstrated track record of meeting or exceeding sales quotas.

o Direct experience selling parcel insurance, shipping insurance, freight insurance, cargo insurance, or a closely related insurance product is strongly preferred/required.

o Experience selling to businesses with meaningful parcel or shipping volumes, preferably within e-commerce, logistics, retail, fulfillment, or shipping technology.

o Proven experience managing the full sales cycle, from prospecting and discovery through negotiation and close.

o Strong understanding of the parcel/shipping insurance market, customer needs, and competitive landscape.

o Demonstrated ability to sell complex or consultative solutions and translate technical or industry-specific concepts into clear business value.

o Strong prospecting, negotiation, presentation, and closing skills.

o Excellent verbal and written communication skills, with the ability to engage effectively with both operational and executive-level stakeholders.

o Strong relationship-building skills and the ability to establish credibility and trust with customers.

o Self-motivated, highly organized, and comfortable working independently in a fast-paced, growth-oriented environment.

o Proficiency with Salesforce or comparable CRM and sales technology.

Preferred Qualifications

o Existing relationships or network within the parcel, freight, logistics, shipping, e-commerce, or insurance ecosystem.

o Experience selling insurance through a technology platform, API, shipping platform, carrier, 3PL, or logistics provider.

o Experience selling to mid-market and enterprise customers.

o Experience working in a startup, high-growth, or newly established business unit.

o Familiarity with shipping technology, parcel management, transportation management systems, or e-commerce infrastructure.

o Experience launching or growing a new product, territory, vertical, or sales channel.

What We Offer:   o Comprehensive medical, dental, vision, and life insurance o Competitive compensation package and equity o Monthly work from home stipend of $50 o Flexible work schedule and paid time off o Collaborative culture with a supportive team o A great place to work with unlimited growth opportunities o The opportunity to make massive contributions at a hyper-growth company o Make an impact on a product helping ship millions of packages per day   Data Privacy Notice for Job Applicants: For information on personal data processing, please see our Privacy Policy: https://www.easypost.com/privacy   "EasyPost is an Equal Opportunity Employer. Employment decisions are made without regard to race, color, religion, national or ethnic origin, sex, sexual orientation, gender identity or expression, age, disability, protected veteran status or other characteristics protected by law."   To be considered for this position, you must be authorized and based in the United States.   If you have any questions or concerns you can reach out to me directly on LinkedIn @KristinaPerna :).   Any communication to applicants relating to the EasyPost hiring process will only come from email addresses with the domains kperna@easypost.com and pcardona@easypost.com. If in the course of the application or hiring process with EasyPost you are contacted through another domain, are requested to provide banking or other sensitive information, or you note any other suspicious activity, please contact recruiting@easypost.com