Director of AI Operations & Delivery

Director of AI Operations & Delivery - SoftWriters 

More than a technology company. 

Empower LTC Pharmacies.

Save Lives.

Build the Future of Healthcare Technology.

About SoftWriters 

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. 

The Opportunity 

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. 

Location: Hybrid - Pittsburgh, PA (Core office days: Tuesday, Wednesday, Thursday) 

Reports to: VP of AI 

What You'll Do 


* Delivery Leadership: Own delivery outcomes for agentic initiatives present and future.

Drive sprint execution, unblock teams, manage dependencies with engineering and IT.


* Blended Team Leadership: Build and lead a high-performance product + engineering team (currently ~4 people; scaling).

Recruit, develop, and retain top talent across product and engineering disciplines.


* Product & Engineering Alignment: Own the day-to-day integration of product thinking and engineering execution.

Define features, roadmap prioritization, and technical tradeoffs with shared ownership.


* Agentic Fleet Operations: Establish processes for creating, deploying, monitoring, and scaling agentic systems.

Own the operational framework for agent lifecycle management and team capability building.


* Technical Depth: 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.


* Cross-Functional Alignment: Partner with VP of Engineering, IT/Cloud leadership (Azure governance), and broader product leadership on roadmap and technical constraints.


* Operational Excellence: Establish metrics, dashboards, and processes for delivery visibility, quality, and risk management.

Scale operations as team grows.

What We're Looking For Required: 


* 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 tran...