Sr Director Architecture and AI Enablement

GuideWell • Jacksonville, FL

5d

About The Position

This critical leadership role sets technology strategy and architecture direction for Engagement Technology. The role drives cloud migration, architectural simplification, and AI adoption across products and engineering practice, partnering with Enterprise Architecture, the AI COE, Data COE, Security, and peer engineering leaders. The successful candidate is credible with engineers and persuasive with executives.

The role leads and grows a high-caliber team, mentors senior engineers and architects, and serves as a member of the Engagement Technology leadership team. It owns architecture direction, AI SDLC transformation, and cloud migration strategy and execution, while aligning technical decisions with business strategy and enterprise priorities.

Requirements

• At least 7 years of related work experience in software engineering and architecture, including enterprise-wide scope for the Senior Director level.
• At least 5 years of direct supervisory or management experience.
• Deep hands-on technical skills across web and mobile, API and event-driven integration, iPaaS, identity, and cloud-native architecture.
• Demonstrated ownership of target-state architecture in a multi-product environment.
• Experience leading cloud migration and modernization programs.
• Practical experience applying AI to the software development lifecycle.
• Proven ability to influence across Enterprise Architecture, Security, and Infrastructure organizations.
• Credibility with engineers and persuasiveness with executives.
• Related bachelor's degree or additional related equivalent work experience in Computer Science, Engineering, or a related field; equivalent combination of education and experience is considered.

Nice To Haves

• Master's degree in Computer Science, Engineering, or a related technical discipline.
• At least 15 years of software engineering and architecture experience, including enterprise-wide scope for the Senior Director level.
• At least 5 years leading architecture or technical transformation at scale.
• At least 10 years of hands-on cloud experience, AWS preferred, including cloud-native, web/mobile, API and event integration, iPaaS, and identity.
• Healthcare, insurance, or other regulated industry experience.
• AI/ML platform and GenAI solution architecture experience.
• Experience with AWS Bedrock and Snowflake Cortex.
• FinOps practices and cloud cost management experience.
• Business or platform transition and integration experience.

Responsibilities

• Drive target-state architecture across product, platform, and integration domains.
• Lead solution architecture for major initiatives and translate business strategy into technical direction.
• Drive architectural simplification and legacy retirement; establish architecture governance and the design review process.
• Serve as the primary interface to Enterprise Architecture, partner with AI Engineering, Data, Security, and Infrastructure COEs, represent the group in enterprise architecture forums, and build alignment with peer leaders.
• Own AI SDLC transformation within Engagement Technology: select, pilot, and scale AI engineering tools; establish standards, guardrails, and secure usage patterns; define and track adoption and productivity measures; and drive enablement, training, and change management.
• Own the cloud migration strategy and execution roadmap; define migration patterns and target cloud architecture; partner with Infrastructure, Security, and FinOps; and provide executive visibility into progress and cost.
• Lead and grow a high-caliber team, mentor senior engineers and architects, and serve on the Engagement Technology leadership team.
• Travel to multiple locations for work, including meetings, events, and conferences, occasionally.

Benefits

• Medical, dental, vision, life, and global travel health insurance.
• Income protection benefits, including life insurance and short- and long-term disability programs.
• Leave programs to support personal circumstances.
• Retirement Savings Plan including employer match.
• Paid time off, volunteer time off, 10 holidays, and 2 well-being days.
• Additional voluntary benefits.
• Comprehensive wellness program.
• Competitive pay and opportunities for incentive or commission compensation.
• Regular annual reviews with pay-for-performance considerations for base pay increases. The description lists an annualized salary range of $180,000–$292,500 and a typical annualized hiring range of $180,000–$225,000.

What This Job Offers

• Job Type: Full-time
• Career Level: Director