Head of Deployments

WHO WE ARE: Kastle is building the AI employee for financial services. We work with some of America's largest banks, helping them scale their operations using autonomous AI Agents that process payments, originate loans, and help customers get a world class experience during some of the biggest financial decisions of their lives. We've processed over $2 billion in transactions and are backed by Insight Partners and Y Combinator. 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. We just raised a $24M Series A and are growing fast! ABOUT THE ROLE Kastle is hiring its first Head of Deployments to build the team that takes our AI agents from signed contract to live production inside banks, lenders and mortgage servicers. Kastle is the AI workforce platform for financial services, starting with consumer lending. Our voice, SMS and workflow agents collect payments, answer borrower questions and qualify loan inquiries, working on top of the systems lenders already run, such as ICE MSP, rather than replacing them. We're a San Francisco team backed by Insight Partners, Y Combinator, Commerce Ventures and Fifth Wall, and we closed a $24M Series A in September 2026. You'll report to the CEO and own every customer deployment end to end. You'll lead forward deployed engineers, deployment PMs and process specialists who embed with lending operations teams, scope workflows, integrate with core systems and get agents into production safely. As we scale across banks and financial institutions globally, you'll turn bespoke rollouts into a repeatable deployment engine. WHAT YOU'LL DO - Build and scale the deployments org. Hire, develop and retain forward deployed engineers, deployment PMs and lending process specialists. Set the hiring bar and team structure as we grow from a handful of deployments to dozens running at once. - Own delivery for every customer. Be accountable for time-to-live, quality and adoption at each bank, credit union, lender and servicer. Run kickoffs, scoping, integration, UAT and go-live, and step in personally on the hardest accounts. - Make deployments repeatable. Turn one-off rollouts into playbooks, reusable integration patterns (servicing cores, LOS, dialers, CRMs) and tooling that cut deployment time with each customer. - Get compliance right from day one. Partner with customers' risk, compliance and InfoSec teams on vendor reviews, model risk management and consumer protection rules (TCPA, FDCPA/Reg F, UDAAP) so agents launch safely and audit-ready. - Feed the product roadmap. Turn what you learn in the field into clear product requirements. Work closely with Engineering and Product on what becomes platform versus what stays custom. - Partner with Sales and Customer Success. Join late-stage deals to scope solutions credibly, define clean handoffs from sale to deployment to ongoing success, and help expand accounts after launch. - Bring operational rigor. Define engagement models and deployment pricing, plan capacity for a scarce team, track deployment metrics, and report customer outcomes to leadership and in customer QBRs. WHAT WE'RE LOOKING FOR - 8+ years in technical, customer-facing roles, with 4+ years leading deployment, solutions engineering, professional services or implementation teams - A track record of building a team or service line from early stage and scaling it through rapid growth - Hands-on experience deploying enterprise software into regulated environments, ideally banks, lenders, mortgage servicers or other financial institutions - Strong technical depth: APIs, system integrations, data pipelines and the SDLC, enough to unblock engineers and earn trust from customer IT teams - Working knowledge of LLMs, AI agents or conversational AI, and sound judgment on where they work in production and where they don't - Commercial instincts: you've scoped and priced services work and supported complex enterprise sales cycles - Clear communicator who can run a room with a bank COO one day and debug an integration with an engineer the next Nice to have - Domain knowledge of consumer lending operations: 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 We encourage you to apply even if you don't meet every qualification.