Technical Program Manager – Conversational AI & Digital Transformation

Location: Miami, FL (Hybrid)

Position Summary

We are seeking a senior Technical Program Manager to lead planning, execution, and delivery across a complex portfolio of Conversational AI and Digital Transformation initiatives. This role requires a strategic operator with strong technical acumen who can drive alignment and accountability across multiple engineering, product, and business teams.

This is not a traditional Project Manager role. The ideal candidate is a seasoned leader who can influence stakeholders, manage complex dependencies, and drive results across teams without direct reporting authority.

Key Responsibilities

• Lead end-to-end program planning, execution, and delivery across multiple technology and business teams.
• Coordinate activities among Digital teams, channel owners, engineering organizations, and executive stakeholders.
• Establish and maintain program governance, milestones, success metrics, and delivery accountability.
• Identify, manage, and resolve cross-functional dependencies, risks, and blockers.
• Drive escalation management and facilitate decision-making to maintain program momentum.
• Partner closely with engineering leadership to ensure alignment between technical execution and business objectives.
• Monitor program health, delivery progress, resource needs, and organizational readiness.
• Facilitate communication across technical and non-technical stakeholders while maintaining transparency and accountability.
• Build strong relationships across teams to drive execution in matrixed organizational environments.

Required Qualifications

• 10+ years of experience leading large-scale technology programs in enterprise environments.
• Proven experience managing complex, cross-functional initiatives involving multiple engineering teams.
• Strong understanding of software development lifecycles, cloud technologies, APIs, integrations, and modern digital platforms.
• Demonstrated success influencing teams and stakeholders without direct management authority.
• Exceptional risk management, dependency management, and executive communication skills.
• Ability to operate effectively in fast-paced, highly visible transformation programs.

Preferred Qualifications

• Prior experience leading Conversational AI, contact center modernization, customer experience transformation, or omnichannel digital initiatives.
• Experience working with enterprise digital platforms and customer engagement technologies.
• Background in travel, hospitality, cruise, or related customer-centric industries.
• Ability to rapidly ramp up and deliver measurable outcomes within aggressive timelines.

Success Profile

The successful candidate is a highly experienced program leader who drives execution through influence, accountability, and collaboration. They are a strong operator who proactively manages complexity, challenges assumptions when necessary, and consistently delivers results across large, matrixed organizations.