Customer Experience Associate

Yesterday's insurance wasn't built for today's risk. We see it in the data and we feel it in the field. Emerging technology can reinvent how risk is priced and managed, faster and smarter, anchored in proven expertise. First-movers will define the next era of commercial risk management, and Shepherd is building it.

Shepherd is a technology-driven Managing General Underwriter (MGU) transforming commercial Property & Casualty insurance for high-hazard industries. Our mission is to make risk frictionless for the builders and operators shaping the physical world, protecting progress from concept through construction and into decades of operation.

We're building the fastest, smartest commercial risk platform, where underwriting expertise, data, and automation work together to deliver:

• Faster decisions

• Smarter, more accurate pricing

• Better risk outcomes

With Shepherd, safety, speed, and quality no longer trade off against one another. They compound. We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services, where technology, underwriting, and partnerships operate in harmony to support the world's most important industries and the progress they make possible.

In March 2026, Shepherd raised a $42M Series B — bringing total funding to over $60M — led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building. Our investors:

• Intact Private Capital, led our Series B round

• Costanoa Ventures, led our Series A round

• Spark Capital, led our Seed round

• Susa Ventures, lead our Pre-Seed round

• Y Combinator

• And several others

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.

We are looking for a motivated and eager individual to join our Customer Experience team who is ready to create impactful customer experiences and do the best work of their career. As a Customer Experience Associate, you'll focus on Client Servicing and Customer Success, working to build customer champions, optimize internal processes, and ensure exceptional end-to-end experiences with Shepherd. This role offers a unique opportunity to be part of a dynamic team and gain exposure to various aspects of our business, including growth, customer service, and process development.

Client Servicing

• Cultivate and maintain strong relationships with broker partners

• Manage post-sales account processes to ensure success for partners and Shepherd

• Own documentation, change management, and ongoing trainings for internal team members

Customer Success

• Expand software offerings with current customers

• Lead customer demos, onboarding, customer meetings, and quarterly business reviews

Customer Experience

• Enhance our customer journey in important areas such as: partnerships, marketing, operations, and customer service related tasks

Process Improvement

• Identify areas for improvement

• Propose solutions and collaborate with cross-functional teams

• You are extremely detail-oriented, organized, and concise

• You are customer centric at core and exhibit this through your work

• You embrace ambiguity

• You are adaptable and welcome new challenges

• You have a strong work ethic, are self-motivated, and have the ability to manage multiple tasks/projects simultaneously in a fast-paced environment

• You exhibit strong communication skills and emotional intelligence

• You are excited about process development and innovation

• Bachelor’s degree or equivalent experience

• You have a minimum of 2+ years of previous experience in customer success, customer service, or operations roles

Shepherd runs on four values. Here's what each one means in this seat.

• Think big, build big. We exist to protect progress and the industries that rely on it. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy.

• Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. As the first PM you set a standard the rest of the team inherits, and the milestones belong to the team rather than to product.

• Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen.

• Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.

🏥 Premium Healthcare
100% contribution to top-tier health, dental, and vision

🥕 Fertility benefits and family building support

🏖️ Unlimited PTO
Flexibility to take the time off, recharge, and perform

🥗 Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

🖥️ SF, NYC, Dallas-Fort Worth, Chicago and LA Offices

📚 Professional Development
Access to premium coaching, including leadership development

🏦 Competitive 401(k) Plan

🐶 Dog-friendly office
Plenty of dogs to play with and make friends with in the SF office