AI Deployments Lead — Scale Lending AI Agents (Equity)

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

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.