Director of Software Engineering - AI-Native Platform

About PerfectServe

PerfectServe is a leading provider of clinical communication and physician scheduling solutions in the health IT space. Founded in 1997, the company has experienced significant growth, particularly after major acquisitions in 2019. With over 400 employees, 30,000+ customers across medical practices, hospitals, and health systems, and over $100 million in annual revenue, PerfectServe is committed to accelerating speed to care by optimizing provider schedules and routing communications. Our mission is to advance patient care and improve clinician well-being through real-time information sharing, better scheduling, and automated clinical workflows. Leading analyst firms like Gartner® and KLAS Research have consistently validated our approach, with PerfectServe being named the segment leader in the Gartner Magic Quadrant™ for Clinical Communication and Collaboration and receiving multiple Best in KLAS awards.

At PerfectServe, you'll join a collaborative team dedicated to innovation, staying on the cutting edge of product development, and integrating AI into our solutions. We are a well-established, tech-forward company where smart people do meaningful work.

About the Role

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 where 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 is ideal for a senior engineer who leads by doing – someone equally comfortable whiteboarding distributed system architecture, diving into an inference pipeline, mentoring junior engineers, and holding external development partners accountable.

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 critically.
• Establish and maintain technical documentation standards across all AI components.

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, 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 full implementation.

Team Leadership & Development

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

External Partner & Vendor Management

• Serve as the primary engineering accountability owner for outsourced development partners, setting quality standards and managing integration.
• 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.

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 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.

Cross-Functional & Strategic Contribution

• Partner with the Director of Product Management to align the technical roadmap with product strategy.
• Represent engineering in executive conversations, translating technical realities into business risk and opportunity language.
• Contribute to PerfectServe’s broader AI strategy, sharing perspectives on emerging capabilities 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.
• 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.
• 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.
• Strong written and verbal communication skills.

Preferred

• Experience in healthcare SaaS, digital health, or regulated software environments.
• Familiarity with contact center platforms, conversational AI, or clinical communication workflows.
• Experience scaling engineering teams in a growth-stage environment.
• Exposure to responsible AI frameworks 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.

Compensation & Benefits

• Salary Range: $160,000–$225,000 USD per year
• Remote-first work environment
• Health, Dental, Vision, Life, and Disability Insurance available day one
• 401K with match and immediate vesting
• 17 company holidays, 2 floating holidays, plus competitive paid time off
• Internal Advancement Opportunities