Weekend Software Support Engineer Jobs in Boston, MA

Who We Are:
Interra Health is a fast-growing healthcare technology company transforming how providers and patients navigate the prescription journey. Formed through the merger of DoseSpot, Arrive Health, and pVerify, Interra Health delivers trusted eligibility, real-time coverage and pricing insights, prescribing tools, and pharmacy transparency at the point of care—helping providers make informed decisions and patients access the right medications with greater clarity and affordability. Backed by strong market momentum and a bold vision for the future of connected care, Interra Health offers the chance to join an innovative, mission-driven team working at the intersection of software and healthcare to reduce friction, improve access, and make the healthcare experience better for everyone.

The Role:

We are looking for a hands-on and operationally minded Lead Developer to own the

health, reliability, and continuous improvement of our mission-critical SaaS platforms. This

role is intentionally designed for a senior engineer who writes production ready code, leads

complex debugging efforts, and sets technical direction for how support-driven engineering

work is executed while simultaneously mentoring and managing a team of application

support engineers.

You will work at the intersection of support, engineering, and operations: triaging escalated

incidents, developing hotfixes, identifying systemic failure patterns, and partnering with

engineering to reduce recurring issues at their root. You bring a forward-looking mindset to

a function that could otherwise be purely reactive — and you use modern AI-assisted

tooling to make your team faster and smarter.

Key Responsibilities:

Incident Management & Technical Triage

• Serve as the primary technical authority for production support code paths, hotfixes, and stability-focused enhancements, performing deep-dive technical triage across the full application stack.

• Analyze logs, traces, database queries, and application behavior to identify root causes rapidly and accurately.

• Develop and communicate clear workarounds to minimize customer impact while permanent fixes are in progress.

• Establish engineering standards for support-owned code, including testing

expectations, deployment safety and rollback strategy.

• Author and deploy targeted hotfixes with appropriate testing and change control,

coordinating production releases on Azure.

• Maintain SLA compliance and ensure accurate, timely ticket documentation

throughout the incident lifecycle.

Proactive Problem Management:

• Monitor production defect and incident patterns analysis to surface recurring or

systemic issues before they escalate.

• Build and maintain a problem registry; translate patterns into actionable engineering proposals with clear business impact framing.

• Drive post-incident reviews (PIRs) and own the follow-through on corrective action items.

• Partner with the product and engineering teams to advocate for platform stability improvements based on real-world support data.

AI-Augmented Support Operations:

• Champion the adoption of AI and automation tools (e.g., Copilot, AI-assisted log

analysis, LLM-based triage assistants) to accelerate issue diagnosis and resolution.

• Lead development of internal knowledge bases, runbooks, and automated

diagnostic playbooks to reduce mean time to resolution (MTTR).

• Identify opportunities to automate repetitive support workflows and implement

tooling improvements.

Technical Debt & Engineering Collaboration:

• Actively engage with the engineering backlog to identify, scope, and prioritize tech debt items impacting platform stability and supportability.

• Contribute to or lead the remediation of targeted tech debt items during allocated engineering cycles.

• Act as a bridge between the support team\'s operational insights and the engineering team\'s roadmap priorities.

Team Leadership & Development:

• Lead, coach, and mentor a team of application support engineers, providing technical guidance and career development support.

• Set team priorities, manage workload distribution, and ensure appropriate on-call coverage.

• Establish and refine team processes — ticket workflows, escalation paths, documentation standards, and quality benchmarks.

• Define and track key performance indicators and align the team around common

goals and continual improvement.

• Conduct regular 1:1s, performance reviews, and foster a culture of accountability,

learning, and continuous improvement.

Required Qualifications:

• 10+ years of experience in application support, software engineering, or a

combined production-focused engineering role — with at least 3 years in a senior or lead capacity.

• Strong hands-on proficiency in .NET / C# for reading, debugging, and writing production-quality code.

• Solid understanding of React front-end applications — ability to diagnose UI-layer issues and interpret browser-side errors.

• Deep experience with Microsoft SQL Server — proficient in query analysis, execution plan review, and performance troubleshooting.

• Demonstrated experience supporting applications hosted on Microsoft Azure (App

Services, Azure SQL, Application Insights, Log Analytics, Azure DevOps, etc.).

• Proven track record of owning complex, high-stakes production incidents end-to-end.

• Experience with structured problem management methodologies (e.g., root cause analysis, 5 Whys).

• Demonstrated ownership of production codebases and responsibility for fixing issues directly in code rather than routing work to another team,

Preferred Qualifications:

• Experience building or deploying AI/LLM-assisted tooling for support operations

(e.g., GitHub Copilot, Azure OpenAI, Claude Code, custom diagnostic bots).

• Familiarity with CI/CD pipelines and deployment automation (Azure DevOps, GitHub Actions).

• Exposure to observability and monitoring tooling (Application Insights, Datadog, Grafana, or similar).

• Background in business critical SaaS environments where multi-tenancy, uptime

commitments, and customer impact sensitivity are top-of-mind. Healthcare industry experience is a plus.

• ITIL Foundation certification or equivalent experience in structured IT service management.

Working Conditions & Environment:

• Fully remote role within the United States

• Periodic travel (approximately 10%) for team meetings, and company events (as

applicable)

• Operates in a fast-paced, growth-oriented, PE-backed SaaS environment

• Requires cross-functional collaboration across Product, Sales, Customer Success,

and Executive Leadership (edit as applicable)

• Ability to manage multiple concurrent product launches and shifting priorities (edit

as applicable)

Success in this role requires the ability to balance synchronous collaboration with

thoughtful asynchronous execution in a remote-first environment

🌍Remote work environment with a flexible work schedule to encourage work-life balance

✈Annual company offsite

🌴Generous leave package including flexible time off policy that encourages team members to take time off to relax and recharge; plus 13 paid holidays, paid sick leave, and paid parental leave

💙 Medical, dental, and vision insurance for you and your family, plus a company funded FSA & HSA (dependent on which medical plan you choose)

💰401(k) company match

💸One-time workspace reimbursement to help you optimize your remote workspace

Interra Health is an Equal Employment Opportunity/Affirmative Action employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, protected veteran status, disability status, sexual orientation, gender identity or expression, marital status, genetic information, or any other characteristic protected by law.