Insurance Sales Representative

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.