Sr. Director, Software Engineering

Innovation Associates, Inc. • US,

3d • $164,618 - $252,415 • Remote

About The Position

We are hiring a Sr. Director of Software Engineering to lead the evolution of the NEXiA core platform — the software foundation that powers every pharmacy automation system we deploy. In this role, you will guide the modernization of a mission-critical .NET/VB6 platform into a more modular, cloud-ready, API-first architecture while ensuring continued reliability for the customers who depend on us every day. You will lead a talented engineering organization through a transformation that is already underway, balancing near-term delivery with long-term platform strategy. This role requires a leader who can bring teams along with clarity, empathy, and conviction; make thoughtful architectural and process decisions; and help move the organization from legacy ways of working toward a more scalable, modern engineering model.

Requirements

• 5+ years in senior engineering leadership (Director or above) managing 40+ engineers
• 12+ years in software engineering, with proven experience modernizing legacy platforms: .NET, VB6, or equivalent monolithic architectures — strangler-fig, domain-driven design, API-first decomposition
• Demonstrated experience leading engineering teams through technical and organizational transformation, including modernization of legacy platforms, adoption of new practices, and change management across established teams
• Experience with AI/ML integration, intelligent automation, or AI-enabled product capabilities, including embedding AI capabilities into existing platforms
• Experience making prioritization, resource allocation, organizational, and talent decisions in support of business and technology objectives
• Strong release engineering discipline, including CI/CD, automated testing, quality gates, and practices that improve release predictability and delivery confidence
• Experience in a PE-backed or high-growth environment: Engineering investment tied to business outcomes (ARR, margin, cost-to-serve)
• Experience leading fully remote or distributed engineering teams across multiple time zones
• Ability to travel based on business needs, including quarterly visits to our New York office, strategic planning meetings and customer engagements. Travel is purposeful and focused on collaboration, customer insights, innovation and delivering meaningful business outcomes.
• Applicants must be authorized to work for ANY employer in the U.S. Employer will not sponsor applicants for work visas.

Nice To Haves

• Healthcare, pharmacy, or regulated industries (FDA, HIPAA, or equivalent compliance environments)
• IoT/fleet telemetry, robotics software, or hardware-software integration
• Pharmacy automation, dispensing systems, or supply chain software
• Platform-as-a-product thinking — building internal platforms that serve multiple product lines
• Databricks, Azure, or cloud data platforms in an enterprise context
• Hands-on experience with microservices migration from monolithic .NET applications

Responsibilities

• Own the technical strategy and execution for the NEXiA core platform (Fulfillment + Retail), including development, release cadence, and quality
• Drive incremental modernization by decomposing the monolith into modules without disrupting production customers
• Converge the forked Fulfillment and Retail codebases into one configurable platform that serves both markets
• Establish automated quality gates, regression suites, and CI/CD pipelines that transform release cadence from "event" to "routine"
• Own the technical roadmap for NEXiA on-prem releases (17.x, 12.x) while building the bridge to cloud-native architecture
• Define and execute the strategy for embedding AI-enabled capabilities into the NEXiA platform, including predictive maintenance, self-healing systems, and workflow optimization
• Partner with Data/ML teams to instrument the NEXiA fleet, including SmartDispenser, SmartPod, 4L canisters, RFID totes, and scales, to support telemetry, predictive uptime, and intelligent automation
• Evaluate and integrate AI/ML capabilities that reduce cost-to-serve, improve self-service capabilities, and support data-driven business value creation
• Support the use of operational data to inform intelligent automation, product capabilities, and long-term platform value
• Lead 40–60+ engineers (direct + matrixed) through a multi-year platform transformation while maintaining delivery commitments to existing customers
• Lead engineering teams through organizational and technical transformation by supporting skill development, establishing clear expectations, and reinforcing modern engineering practices
• Restructure teams from technology-aligned silos to product-aligned squads that own modules end-to-end by value stream
• Establish dedicated support structures to maintain operational continuity and protect current customer commitments while product-aligned teams advance modernization priorities
• Establish engineering metrics (deployment frequency, change-failure rate, % logic under test, % features shared across markets) and hold teams accountable
• Prioritize, sunset, or discontinue features and initiatives that do not align with platform strategy, business priorities, or long-term scalability
• Evaluate customer-specific commitments against platform standardization goals to support scalable product development and reduce unnecessary customization
• Communicate delivery risks, prioritization tradeoffs, and resource constraints early to support informed decision-making and sustainable execution
• Make organizational and talent decisions that align team capabilities, roles, and operating models with transformation objectives
• Partner with Product to ensure engineering investment maps to customer value, ARR growth, and margin improvement
• Collaborate with Cloud, Data Platform, and Hardware teams on shared dependencies (PMSS Connect, N.io, STA, fleet telemetry)
• Work with Customer Success and Field Engineering to reduce cost-to-serve through self-service tooling, remote management, and modular APIs

Benefits

• Generous time off policy that allows you to put your family first
• Opportunity to work on the cutting edge of pharmacy automation in a high growth tech company
• Competitive benefits, salary, and talent development opportunities
• Commitment to professional development and working for a company where your voice is heard

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed