Engineering Team Lead – Appointment Scheduling

This is a fully remote position, open to applicants in Massachusetts.

📋 Description

• Take ownership of the planning, prioritization, delivery process, and daily operations of the Appointment Scheduling team.

• Ensure the team consistently delivers at an enterprise scale.

• Develop and mentor engineers across all levels, including senior and principal individual contributors.

• Collaborate with the Principal Engineer on architectural choices and the products that are released.

• Work alongside Product and Design teams to address customer challenges.

• Direct the technical strategy for the scheduling platform, encompassing availability, booking, routing, reminders, and various customer channels.

• Update the established scheduling core through practical modernization, enhanced test coverage, and streamlined API surfaces.

• Define and advance data architecture and service boundaries to accommodate scale and AI extensibility.

• Uphold the platform's reliability standards.

• Lead the integration of an AI-enhanced software development lifecycle across design, code generation, testing, code review, and legacy modernization.

• Set guidelines for AI-supported development with robust testing and CI/CD practices.

• Stay updated on agentic development patterns, including MCP-based tools, and enhance team proficiency.

• Introduce intelligent product features such as conversational booking, availability recommendations, reduced no-show rates, and proactive customer engagement.

• Ensure AI functionalities utilize verified availability data and are assessed against clear success metrics.

• Collaborate with the Principal Product Manager to align AI product initiatives with customer value and the scheduling roadmap.

⛳️ Requirements

• Proven experience leading an engineering team to deliver processes, planning, and results while maintaining a hands-on technical role.

• Background in product shipping, not just team management.

• Expertise in JVM backend technologies, including Java, Spring Boot, and Java 17.

• Experience with modern TypeScript front-end frameworks such as React and/or Angular.

• Familiarity with high-throughput services and relational data.

• Experience in modernizing large, mature, business-critical systems without business disruption.

• Proficiency with AI coding agents and AI-augmented development.

• A genuine sense of product design focused on enhancing the customer booking experience.

• Based in the United States.

• Willingness to travel occasionally for team and customer engagements.

• Previous experience in scheduling, calendaring, availability modeling, or resource optimization is a plus.

• Depth in SQL and relational data is advantageous.

• Experience in enterprise-scale API design and integration is beneficial.

• Background in financial services, banking, credit unions, healthcare, or retail technology is a plus.

• Experience in exposing platform capabilities to AI agents using MCP or similar frameworks is desirable.

• Familiarity with SQL Server, PostgreSQL, Scala/Akka, Kubernetes on AWS, Claude models, and MCP-based agent tooling is not required, but relevant to the role.

🏝️ Benefits

• Willingness to travel occasionally for team and customer meetings.

• AI-augmented development lifecycle and exposure to AI agent tooling.

• Opportunity to work with Claude models and MCP-based agent tooling.