Head of AI Delivery & Operations

SoftWriters, Inc.; Pittsburgh (Allegheny County); Hybrid; USD 180,000 - 240,000; Full time

Benefits offered by this job

Hybrid work policy

Remote-Work Bank

Birthday PTO

401(k) with company match

Comprehensive medical coverage

Job summary

SoftWriters in Pittsburgh is seeking a Director of AI Operations & Delivery to lead the Alpha Lab's agentic AI platform initiatives, driving delivery outcomes and scaling operations across product and engineering teams. You will own features, roadmaps, and technical tradeoffs with shared ownership and accountability.

You will manage a blended product + engineering team, recruit top talent, and ensure alignment between product thinking and engineering execution while advancing agentic systems and

Qualifications

• 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

Responsibilities

• Delivery Leadership: Own delivery outcomes for agentic initiatives; drive sprint execution and unblock teams.
• Blended Team Leadership: Build/lead a product + engineering team; recruit and retain talent.
• Product & Engineering Alignment: Define features, roadmap prioritization, and tradeoffs.
• Agentic Fleet Operations: Establish processes for creating, deploying, monitoring, and scaling agentic systems.
• Technical Depth: Maintain hands-on familiarity with agentic architecture, cloud infra (Azure), and LLM integrations.
• Cross-Functional Alignment: Partner with VP of Engineering, IT/Cloud leadership, and product leadership.
• Operational Excellence: Establish metrics, dashboards, and processes for delivery visibility, quality, and risk management.

Skills

Delivery leadership

Blended team leadership

Product & engineering alignment

Agentic fleet operations

Technical depth

Cross-functional collaboration

Job description

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 ForRequired:

• 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 HereMeaningful 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
• 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.

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities
This employer is required to notify all applicants of their rights pursuant to federal employment laws.For further information, please review the Know Your Rights notice from the Department of Labor.