AI Deployments Lead

Kastle (YC S24); San Francisco (CA); On-site; USD 200,000 - 250,000; Full time

Benefits offered by this job

Health membership

MLO training

Medical coverage

401K plan

Paid meals

Offsites

Job summary

Kastle is hiring for a strategic customer-facing role to lead end-to-end deployments of AI agents in consumer lending. You will guide deployments, drive adoption, and ensure customers achieve measurable value across complex workflows.

You will collaborate with Engineering and Sales to surface needs, shape product outcomes, and scale the ASM function. Candidates should have strong LLM experience and comfort with compliance-focused environments in a high-growth setting.

Qualifications

• 4+ years in a high-rigor customer-facing role (e.g., technical account management, solutions engineering, implementation, consulting, or banking).
• Hands-on LLM experience: you've built agents, understand evals, and can reason about agent failures.
• Comfort reading API docs and understanding webhooks, integrations, data mapping, and data pipelines.
• Strong judgment in ambiguous, high-stakes customer situations.
• Experience collaborating with executive stakeholders across operations, compliance, product, engineering, and commercial teams.

Responsibilities

• Own our most strategic deployments end-to-end—timeline, health, adoption, and the customer relationship.
• Identify and drive upsell and expansion opportunities across accounts to grow net ARR.
• Analyze transcripts, logs, prompts, and evals to explain agent behavior to compliance, ops, and engineering teams.
• Write, test, and ship prompt and logic changes as customer workflows and compliance requirements evolve.
• Stand up an AI-powered CSM layer using third-party tooling and keep it current.
• Own our ticketing system and continuously improve it to be world-class.
• Collaborate with engineering to surface insights, e.g., end-of-day reports on failed calls and fixes.
• Push back when a customer ask or sales commitment doesn’t align with product/tech/compliance realities.

Skills

Customer-facing experience

LLM experience

Cross-functional collaboration

Executive stakeholder alignment

Job description

About Kastle

Kastle is building the AI employee for consumer lending. We work with some of America's largest banks and mortgage lenders, helping them scale their contact center and compliance operations using autonomous AI Agents that process payments, originate loans, and help customers get a world class experience during the biggest financial decisions of their lives.

Kastle is building the AI employee for consumer lending. We work with some of America's largest banks and mortgage lenders, helping them scale their contact center and compliance operations using autonomous AI Agents that process payments, originate loans, and help customers get a world class experience during the biggest financial decisions of their lives. We\'ve processed over $1 billion in transactions and are backed by Y Combinator and Commerce Ventures. If you are interested in building AI that is applied in the real world where precision, reliability, and performance matter and redefine access to credit across the world, apply below.

About The Role

You’re joining at an inflection point. Our usage has grown 40x in the last 6 months and our Agent Product and Success team is a high impact group that shapes how customers use and gain value from our product. You will start by partnering closely with customers to guide deployments, support adoption and ensure they have the tools and insight they need to achieve meaningful outcomes. Overtime you will step in as the leader and own every deployment across the company. You will work cross functionally with Engineering and Sales to surface customer needs, solve challenges and help shape how our technology performs in real world environments.

What You\'ll Do

• Own our most strategic deployments end to end — timeline, health, adoption, and the customer relationship


• Find and drive upsell and expansion opportunities across every account, growing net ARR


• Dig into transcripts, audit logs, prompts, and evals to explain agent behavior to customer compliance, ops, and engineering teams


• Write, test, and ship prompt and logic changes as customer workflows and compliance requirements evolve


• Stand up an AI-powered CSM layer using third-party tooling and keep it current


• Own our ticketing system and make it world-class


• Vibe-code the V0s of internal tooling with engineering, for exmaple - end-of-day reports on every failed call and what to fix


• Push back when a customer ask or sales commitment doesn\'t match technical or compliance reality

Requirements

• 4+ years in a high-rigor customer-facing role: technical account management, solutions engineering, implementation, consulting, or banking


• Hands-on LLM experience. You\'ve built agents, understand evals, and can reason about why an agent failed.


• Comfort reading API docs and understanding concepts like webhooks, integrations, data mapping, and data pipelines


• Strong judgment in ambiguous, high-stakes customer situations


• Experience working with executive stakeholders across operations, compliance, product, engineering, and commercial teams


• Comfort saying “no” or “not yet” when the ask does not match product, technical, or compliance reality


• High energy. Customers and teammates genuinely love working with you

Why join Kastle

• Opportunity to work with a world class team building a generational AI company that will redefine how every loan in America is made and managed


• Competitive Compensation + Meaningful Equity at a high growth company


• High ownership and direct input on product direction, company culture, and how the ASM function scales

Other Perks And Benefits

• Free Health and Wellness Membership


• Free MLO training and support


• Robust medical, vision, & dental coverage


• 401(K) plan offering


• Paid Company Meals


• Company offsites to get to know the team

Compensation Range: $200K - $250K