Engineering Team Lead, Appointment Scheduling

Engageware•Boston, MA

2d•Remote

About The Position

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.

Requirements

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 Haves

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.

Responsibilities

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.
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.
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.
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.