Director of AI Operations & Delivery

Softwriters•Pittsburgh, PA

56d•Hybrid

About The Position

SoftWriters develops innovative IT solutions that empower long-term care (LTC) pharmacies to deliver life-saving medications more efficiently and accurately. As a voted top workplace in Pittsburgh, we combine meaningful work with a collaborative culture where your contributions directly impact patient care. We're seeking a Director of AI Operations & Delivery to join our growing Alpha Lab team and help shape the future of healthcare technology. In this role, you'll lead the execution and delivery of SoftWriters' agentic AI platform initiatives, driving operational excellence across product and engineering teams while helping define the next generation of AI-powered healthcare solutions.

Requirements

5+ years in software engineering, product management, or engineering leadership
3+ years managing high-performance blended or cross-functional teams (product + engineering preferred)
2+ years hands-on experience with AI/ML systems, agentic systems, or orchestration platforms
Deep technical depth in at least one of: cloud architecture (Azure/AWS), distributed systems, agent frameworks, LLM integrations, or platform engineering
Proven ability to bridge product and engineering, comfortable translating between product vision and technical execution
Demonstrated success in startup or R&D environments

Nice To Haves

Experience with agentic systems, multi-agent orchestration, or AI-driven automation
Healthcare, pharmacy, or regulated industry background
Experience scaling cross-functional teams in innovation labs or R&D centers
Strong product mindset: roadmap prioritization, customer/user empathy, go-to-market thinking
AWS or Azure cloud infrastructure expertise
Background in SDLC best practices

Responsibilities

Own delivery outcomes for agentic initiatives present and future.
Drive sprint execution, unblock teams, manage dependencies with engineering and IT.
Build and lead a high-performance product + engineering team (currently ~4 people; scaling).
Recruit, develop, and retain top talent across product and engineering disciplines.
Own the day-to-day integration of product thinking and engineering execution.
Define features, roadmap prioritization, and technical tradeoffs with shared ownership.
Establish processes for creating, deploying, monitoring, and scaling agentic systems.
Own the operational framework for agent lifecycle management and team capability building.
Maintain hands-on familiarity with agentic architecture, cloud infrastructure (Azure), agent frameworks, and LLM integrations.
Contribute to architectural decisions; unblock engineering on technical design questions.
Partner with VP of Engineering, IT/Cloud leadership (Azure governance), and broader product leadership on roadmap and technical constraints.
Establish metrics, dashboards, and processes for delivery visibility, quality, and risk management.
Scale operations as team grows.