Director of Software Engineering - US Remote

PerfectServe is seeking a Director of Software Engineering to own the architecture, development, and continuous evolution of our AI-native answering service platform. This is a hands-on leadership role — you will set technical direction, make architectural decisions, write and review production code on critical systems, and build the engineering team as the platform scales. Reporting directly to the CTO, you will be a key technical voice in shaping how AI is applied across PerfectServe's clinical communication and contact center products.

This role suits a senior engineer who leads by doing: someone equally comfortable whiteboarding a distributed system architecture, diving into a failing inference pipeline, mentoring an early-career engineer, and holding an external development partner accountable to quality standards.

Core Responsibilities

AI-Native Platform Architecture & Ownership

• Own the end-to-end technical architecture of the AI answering service, including voice pipeline design, LLM orchestration, API integration layers, and real-time telephony infrastructure.
• Define and enforce architectural patterns for AI system reliability, latency management, failure recovery, and scalability across production environments.
• Make build-vs-buy-vs-integrate decisions for new AI capabilities; evaluate third-party models, frameworks, and platforms with a critical engineering eye.
• Establish and maintain technical documentation standards across all AI components, ensuring accuracy is kept current as systems evolve.

Hands-On Engineering Contribution

• Actively participate in design reviews, code reviews, and technical spike work — especially for high-risk or high-complexity components.
• Lead the implementation of core platform components where needed, including AI service integrations, orchestration logic, and platform APIs.
• Diagnose and resolve complex production issues including inference latency, integration regressions, and telephony quality problems.
• Prototype and validate new AI capabilities before committing to full implementation cycles.

Team Leadership & Development

• Build and lead a high-performing engineering team as headcount grows; initially operate as both a technical lead and individual contributor.
• Hire, onboard, and develop engineers with a focus on AI/ML fluency, software craftsmanship, and a bias toward continuous improvement.
• Foster a culture of psychological safety, technical rigor, and iterative delivery — where engineers learn from failure as readily as from success.
• Conduct regular 1:1s, provide candid performance feedback, and create individualized growth plans for direct reports.

External Partner & Vendor Management

• Serve as the primary engineering accountability owner for outsourced development partners as required; setting quality standards, reviewing deliverables, and managing the integration of external work into production systems.
• Evaluate third-party AI platforms, cloud services, and tooling; make and document vendor selection decisions.
• Ensure security, compliance, and data governance requirements are embedded into partner contracts and delivery expectations.

Engineering Operations & Delivery Excellence

• Define and track engineering KPIs: deployment frequency, system uptime, latency SLAs, error rates, and mean time to recovery.
• Lead the team's adoption of modern development practices including AI-augmented development workflows, automated testing for ML outputs, and continuous deployment pipelines.
• Own the engineering budget and resource allocation; communicate tradeoffs clearly to the CTO.
• Collaborate with Product, Clinical, and Operations to translate requirements into reliable, scalable software — and to push back constructively when timelines or scope are unrealistic.

Cross-Functional & Strategic Contribution

• Partner with the Director of Product Management to align technical roadmap sequencing with product strategy and customer commitments.
• Represent engineering in executive conversations; translate technical realities into business risk and opportunity language.
• Contribute to PerfectServe's broader AI strategy, sharing perspectives on emerging capabilities, architectural evolution, and responsible AI practices.

Qualifications

Required

• 10+ years of software engineering experience, with at least 4 years in a technical leadership role with direct reports.
• Demonstrated hands-on experience designing and operating AI/ML or NLP systems in production — not just overseeing teams that build them.
• Deep familiarity with LLM integration patterns, prompt engineering pipelines, retrieval-augmented generation (RAG), and AI evaluation frameworks.
• Strong command of cloud-native architecture on AWS, including serverless, containerization, and event-driven patterns.
• Experience with real-time communication systems (voice/telephony infrastructure, VoIP, WebRTC, or similar) is a significant advantage.
• Proficiency in at least two of the platform's core languages/frameworks: Python, C#, .NET, React.
• Track record of delivering high-reliability SaaS products with defined uptime and latency requirements.
• Experience managing or collaborating with outsourced development partners, including quality oversight and delivery accountability.
• Strong written and verbal communication; able to present technical strategy clearly to non-technical executives.

Preferred

• Experience in healthcare SaaS, digital health, or regulated software environments (HIPAA familiarity a plus).
• Familiarity with contact center platforms, conversational AI, or clinical communication workflows.
• Experience scaling engineering teams from small to mid-size in a growth-stage environment.
• Exposure to responsible AI frameworks, model safety practices, and human-in-the-loop system design.

Why This Role

You will have direct ownership of one of PerfectServe's most strategically important platforms, with the latitude to make consequential technical decisions and the support of a CTO who values engineering craft. This is an opportunity to build something meaningful — AI infrastructure that changes how healthcare organizations communicate and serve patients — while growing into a VP-level leader as the team scales.
Why Join PerfectServe?

At PerfectServe, we are transforming healthcare communication and collaboration to help clinicians deliver better care. You’ll work with a dedicated and mission‑driven team in an environment that values growth, transparency, and innovation.

We offer a salary range of $160,000–$225,000 USD per year, with compensation tailored to your background, strengths, and growth potential. This range reflects our commitment to pay transparency and is based on market data, internal equity, and the scope of responsibilities. Compensation is determined by several factors, including experience, skills, and team impact. We regularly review compensation to ensure fairness and consistency. Current employees with questions are encouraged to connect with their manager or People Operations.