Customer Experience Associate

What We Do

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.

Our Investors

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

Our Team

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

About You

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.

Responsibilities

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 would be a dream candidate if…

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

How we work

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.

Benefits

• 🏥 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