Customer Experience Associate

Shepherd | $90,000 – $125,000

Steph's Notes:

We're entrepreneurs, dreamers, and leaders from across both tech and insurance. We're here to shape the future of financial services for the world's most important industries.

It's an AI company. I know, you're shocked.

Shepherd's Careers page is pretty run-of-the-mill AI fare (although certainly not as obnoxious as some I've seen, so there's that).

The infrastructure behind the AI boom — data centers, semiconductor fabs, renewable energy assets — has to be built and insured.

Does it, though?

Sorry, sorry. Back to the job.

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.

Not for those looking to create forgettable CX and do the shittiest work they've ever done! (Also, curious if there's going to be an attention to detail requirement after that sentence.)

As a Customer Experience Associate, you'll focus on Client Servicing

I really wish they'd have used a different term there.

I'm not going to quote all of them here, but almost all of the responsibilities are too senior for this title. It sounds like they want a senior CSM or even a lead, so I'm not at all sure why they've titled this the way they have.

You are extremely detail-oriented, organized, and concise

Bloviators in constant disarray should not apply! (Also, didn't I tell you?)

You are customer centric at core

Are they going to ask this person to also proofread their job descriptions?

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

This is like 5 red flags in two sentences.

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

Good to know that Shepherd only provides PTO so that their monkey can dance faster!

Role/duty misalignment and poor culture signals; this is a pretty clear BINGO.

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Original Job Description: Customer Experience Associate

What We Do

Shepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered. 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.

The infrastructure behind the AI boom — data centers, semiconductor fabs, renewable energy assets — has to be built and insured. But traditional carriers weren't built for this speed:

• Complex commercial construction projects routinely wait weeks for a single quote
• Legacy carriers rely on static applications and disconnected systems
• Brokers chase carriers through calls, emails, and resubmissions

We built Shepherd to solve that. Our AI performs the same underwriting workflows in seconds, and integrates real-time data from construction technology partners — Procore, Autodesk, OpenSpace, DroneDeploy, and others — to see risk as it actually exists, not just as it was reported on a static form.

We're pursuing the most ambitious technical vision in commercial insurance: fully autonomous underwriting. We're closing in on the first fully agentic submission in the industry — email in, price out, no human intervention until the last mile.

With Shepherd, safety, speed, and quality no longer trade off against one another — they compound. We're building:

• Faster decisions
• Smarter, more accurate pricing
• Better risk outcomes for insureds who invest in safer practices

We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services.

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
• Spark Capital
• Costanoa Ventures
• Y Combinator
• Susa Ventures
• 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

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

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