Director of AI Operations & Delivery - SoftWritersThe 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.
