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 translating between product vision and technical execution
Demonstrated success in startup or R&D environments

Preferred

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

Why You'll Love Working Here Meaningful Work: Your leadership will directly influence AI-powered solutions that improve patient safety and enable pharmacies to deliver better care.

Modern Work Environment: Brand new, high-tech office with stunning Pittsburgh city views, located directly on the North Shore waterfront.

Recognized Top Workplace: Consistently voted one of the best places to work in Pittsburgh.

Work-Life Balance

Hybrid work policy with flexible hours
Remote-Work Bank for additional flexibility
Paid parking provided
PTO day on your birthday
Floating holidays

Comprehensive Benefits

Competitive salary
100% paid parental leave
401(k) with company match
Comprehensive medical, dental, and vision coverage
Life and disability insurance

Growth-Focused Culture

Continuous learning and development opportunities
Cross-functional collaboration
Clear career advancement paths

Our Values in Action

Innovators, Thought Leaders, Teachers: We invest in your growth and encourage knowledge sharing.
Accountability and Ownership: Take initiative, own outcomes, celebrate wins.
Customer-Centric: Direct connection to the pharmacies and patients we serve.
Unyielding Integrity: Ethical decision-making in everything we do.
One Team, Family Spirit: Collaborative environment where everyone's success matters.

Ready to Apply? Join a team where your technical leadership can transform healthcare through cutting-edge AI innovation. We're looking for a visionary leader who can drive execution, scale teams, and help build the future of intelligent pharmacy technology.

Note: This position does not sponsor work visas and requires ability to work hybrid from our Pittsburgh office. Relocation assistance is not provided.

SoftWriters, Inc. is an equal opportunity employer. All qualified candidates will receive consideration for employment without regard to race, color, religion, gender, sexual orientation, national origin or citizenship status, age, disability, genetic information, or veteran status.