About the Role
Engageware powers appointment scheduling for some of the largest banks, credit unions, healthcare systems, and retailers in the world - on the order of a million appointments and interactions a day. When someone books time with their bank or schedules a visit with their care team, our platform finds the right availability, the right person, and the right place, and makes it effortless: online, in the branch, at the kiosk, in the walk-in queue, or virtually, with reminders and routing handled end to end.
We're looking for a hands-on Team Lead to own how the Appointment Scheduling team runs - the process, planning, and delivery - and to drive its technical direction. You'll grow the engineers around you, keep the team healthy and shipping, and carry our platform into the AI age: an AI-augmented development lifecycle where agents do real work across design, code, test, and review, and a product where booking is conversational, availability is intelligent, and every answer is grounded in real, verified data.
What You'll Do
Team & Delivery Leadership
- Own the team's planning, prioritization, and delivery - the process and the day-to-day execution - ensuring the Appointment Scheduling team ships reliably at enterprise scale.
- Grow and coach engineers at all levels (including senior and principal ICs); keep the team engaged, healthy, and improving.
- Partner closely with the Principal Engineer to translate the hardest architectural decisions into reliable, shipped product.
- Collaborate with Product and Design so that what ships solves the customer's actual problem, not just the technical one.
Technical Direction
- Own the overall technical direction for your area of the scheduling platform: the availability and booking engine, routing and reminders, and the online/branch/kiosk/queue/virtual channel experiences built on top.
- Make the mature, business-critical scheduling core safer and faster to change - through pragmatic modernization, improved test coverage, and cleaner API surfaces - without big-bang rewrites.
- Shape and evolve the platform's data architecture (SQL Server, PostgreSQL) and service boundaries (Spring Boot, Scala/Akka) to support scale and AI extensibility.
- Maintain Engageware's reliability bar: the scheduling platform cannot let a customer down.
AI-Augmented Development Lifecycle
- Lead the team's adoption of an AI-augmented SDLC - putting AI agents (built on Claude) to work across design, code generation, test authoring, code review, and legacy modernization.
- Set the team's norms and guardrails for AI-assisted development, with a strong test and CI/CD backbone ensuring AI-generated changes ship fast and safely.
- Stay current on agentic development patterns (including MCP-based tooling) and raise the team's fluency over time.
AI in the Product
- Bring intelligent capabilities into the Appointment Scheduling product where they earn their place: conversational and assisted booking, smarter availability recommendations, reduced no-show rates, and proactive engagement.
- Ensure all AI-driven features are grounded in real, verified availability data - never hallucinated - and are evaluated honestly against clear success metrics.
- Partner with the Principal PM to align AI product bets with customer value and the broader scheduling roadmap.
What We're Looking For
Must-have qualifications:
- A track record of leading an engineering team to deliver: owning process, planning, and outcomes, while staying technically hands-on. You've shipped product, not just run a team.
- Depth in the Appointment Scheduling tech stack: JVM backend (Java / Spring Boot, Java 17) and modern TypeScript front ends (React and/or Angular), with comfort in high-throughput services and the relational data behind them.
- Experience modernizing large, mature, business-critical systems - making them safer and faster to change without disrupting the business.
- Fluency with AI coding agents and AI-augmented development; ideally you've helped a team adopt AI across the SDLC, and you've shipped real LLM/AI features into production with clear-eyed judgment about where AI helps and where it doesn't.
- Genuine product sense: you care about the booking experience the customer feels, not only the architecture behind it.
- Based in the United States, with willingness to travel occasionally for team and customer meetings.
Nice to Have
- Prior experience with scheduling, calendaring, availability modeling, or resource-optimization problems.
- SQL and relational data depth; API design and integration experience at enterprise scale.
- Background in financial services, banking, credit unions, healthcare, or retail technology.
- Experience exposing platform capabilities to AI agents via MCP or similar patterns.
Our Stack
Knowing our stack is not a requirement, but this is what you'll be working with:
- Backend: Mature Java scheduling engine; Spring Boot (Java 17) services; Scala/Akka services
- Frontend: Modern Angular and React applications
- Data: SQL Server and PostgreSQL
- Infrastructure: Kubernetes on AWS
- AI: Claude models (Anthropic), with MCP-based agent tooling
