Head of Deployments

Kastle • San Francisco, CA

1d

About The Position

Kastle is hiring its first Head of Deployments to build the team responsible for taking its AI agents from signed contract to live production inside banks, lenders, and mortgage servicers. Kastle’s AI workforce platform for financial services starts with consumer lending. Its voice, SMS, and workflow agents collect payments, answer borrower questions, and qualify loan inquiries while working with lenders’ existing systems rather than replacing them.

The Head of Deployments will report to the CEO and own every customer deployment end to end. The role leads forward deployed engineers, deployment project managers, and process specialists who work with lending operations teams to scope workflows, integrate with core systems, and safely put agents into production. As Kastle expands across banks and financial institutions globally, this leader will build a repeatable deployment engine from bespoke customer rollouts.

Requirements

• At least 8 years of experience in technical, customer-facing roles.
• At least 4 years leading deployment, solutions engineering, professional services, or implementation teams.
• Track record of building a team or service line from an early stage and scaling it through rapid growth.
• Hands-on experience deploying enterprise software in regulated environments, ideally banks, lenders, mortgage servicers, or other financial institutions.
• Strong technical depth in APIs, system integrations, data pipelines, and the software development life cycle, sufficient to unblock engineers and earn trust with customer IT teams.
• Working knowledge of LLMs, AI agents, or conversational AI, with sound judgment about their appropriate use in production.
• Experience scoping and pricing services work and supporting complex enterprise sales cycles.
• Clear communication skills and ability to engage with senior bank leaders and technical engineers.

Nice To Haves

• Knowledge of consumer lending operations, including servicing, collections, loss mitigation, or originations.
• Experience with servicing and lending systems such as ICE MSP, Black Knight, Encompass, or similar cores.
• Background with voice or contact-center technology.
• Prior early-stage startup experience.

Responsibilities

• Build and scale the deployments organization; hire, develop, and retain forward deployed engineers, deployment project managers, and lending process specialists, and establish hiring standards and team structure.
• Own delivery for every customer, including time to live, quality, and adoption; run kickoffs, scoping, integration, user acceptance testing, and go-live, and personally support the most challenging accounts.
• Create deployment playbooks, reusable integration patterns, and tooling to make rollouts repeatable and reduce deployment time.
• Work with customer risk, compliance, and information security teams on vendor reviews, model risk management, and consumer protection requirements so agents launch safely and are audit-ready.
• Translate field learnings into product requirements and work with Engineering and Product to determine what becomes part of the platform versus custom work.
• Partner with Sales and Customer Success on late-stage deal scoping, handoffs from sales to deployment and ongoing success, and account expansion after launch.
• Establish engagement models and deployment pricing, plan capacity, track deployment metrics, and report customer outcomes to leadership and in customer QBRs.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed