Senior Technology Lead

Our client is building a high-volume, growth-stage platform in the telehealth and e-commerce space. Their product supports complex patient journeys, transactional systems, and pharmacy integrations, with a strong emphasis on scalability, data integrity, and long-term maintainability as the business continues to grow.

Location

Fully remote | 9 AM - 5 PM EST

Role Overview

The Senior Technology Lead is a hands-on Ruby on Rails engineer responsible for owning complex data models and overall system architecture within a Rails monolith. This role leads design decisions for how business domains map into tables, relationships, background jobs, and services, while actively contributing code and mentoring a small team.

A core focus of this role is designing and evolving the domain model that supports intakes and patient journeys, carts and checkouts, orders and subscriptions, and pharmacy and telehealth integrations. You will ensure the platform’s data model and architecture remain coherent, scalable, and maintainable as product complexity and transaction volume increase.

Key Responsibilities

Data Modeling & Architecture Leadership

• Lead data modeling and system architecture decisions across the platform.

• Design tables, relationships, constraints, and schemas for new domains.

• Evolve existing production schemas safely without breaking critical flows.

• Maintain a clear, well-documented, and consistent data model.

• Structure data to support analytics, reporting, and future product features.

• Balance speed, safety, and long-term maintainability in architectural decisions.

End-to-End Feature Ownership

• Own the delivery of complex features within the Rails monolith.

• Build and maintain intakes, eligibility flows, and clinical and operational workflows.

• Develop carts, checkouts, discounts, subscriptions, and renewal logic.

• Own order lifecycles including refunds, retries, and payment reconciliation.

Full-Stack Development

• Work across Rails models, controllers, views, and background jobs.

• Use Hotwire (Turbo and Stimulus) to deliver modern, server-driven UX.

• Implement targeted React components where they provide clear value in the dashboard.

Leadership & Mentorship

• Mentor mid-level engineers and future junior developers.

• Review code with a strong emphasis on data modeling, architecture, and maintainability.

• Set and enforce patterns and standards for models, services, and modules.

Product & Stakeholder Collaboration

• Work directly with product partners and founders to translate business requirements into technical designs.

• Break work into coherent projects and ClickUp tasks.

• Clearly communicate trade-offs and propose pragmatic technical solutions.

Production Readiness & Operations

• Design and execute safe, reversible database migrations.

• Own background job architecture, Solid Queue usage, and operational resilience.

• Contribute to observability and monitoring using Grafana and related tooling.

Qualifications

Experience

• 10+ years of professional software engineering experience, with a strong focus on MVC web frameworks.

• Deep, hands-on Ruby on Rails experience within a substantial production monolith.

• Proven experience designing schemas that accurately reflect business domains.

• Experience evolving live production databases without downtime.

• Experience building and maintaining transactional systems involving carts, checkouts, orders, subscriptions, promotions, refunds, and payment flows.

• Experience integrating with payment gateways and handling webhooks.

• Experience in telehealth or healthcare environments is a plus.

• Experience working on GLP-1 or weight-loss related products is a plus.

• Experience in startup or early-stage environments is a plus.

Skills

• Advanced Rails expertise across routing, models, controllers, views, and background jobs.

• Strong data modeling and system architecture skills, with attention to performance and future scalability.

• PostgreSQL schema design, indexing, and query optimization for transactional and reporting workloads.

• Full-stack capability using HTML, CSS, JavaScript, Hotwire, and targeted React.

• Familiarity with Fly.io, Solid Queue, PlanetScale, and Grafana is a plus.

• Ability to lead architectural discussions, enforce standards, and mentor other engineers.

• Clear written and verbal communication skills.

• Self-sufficient, proactive work style with comfort operating at high velocity.

• Preference for simple, core Rails patterns and avoiding unnecessary dependency stacks.

Opportunity

This is a high-impact role for a senior engineer who wants to own architecture, guide a growing team, and build scalable systems in a complex, regulated domain. You’ll have direct influence over technical direction, domain modeling, and long-term platform health while remaining deeply hands-on in a production Rails codebase.

Application Process:

To be considered for this role these steps need to be followed:

• Fill in the application form

• Record a video showcasing your skill sets