Director of Software Engineering - US Remote

## About the Role - 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. - 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. - 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. - 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. - 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. - 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 role offers the opportunity to shape the future of AI in clinical communication and contact center solutions.