Senior Director, Architecture and AI Enablement

GuideWell Source

. Set technology strategy and architecture direction for Engagement Technology .

Posted 10/17/2026full-timeJacksonville • Florida • United StatesSenior💰 $180,000 - $292,500 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in technology strategy and architecture direction, with a strong focus on cloud migration, AI integration, and team leadership. Proven ability to translate business strategies into technical solutions while establishing governance and driving architectural simplification.

Highest-signal resume keywords

Cloud Migration StrategyAI SDLC TransformationSolution Architecture LeadershipEnterprise Architecture CollaborationTeam Mentorship and Development

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Hard Skills

Software EngineeringArchitecture DesignCloud-Native ArchitectureAPI IntegrationEvent-Driven IntegrationIPaaSAI Application in Software DevelopmentTarget-State ArchitectureArchitectural GovernanceLegacy System Retirement

Soft Skills

Influencing Across OrganizationsCredibility with EngineersPersuasiveness with Executives

Tools & Technologies

Cloud PlatformsAI ToolsIntegration ToolsDevelopment Tooling

Industry Keywords

Enterprise ArchitectureCloud MigrationSoftware Development LifecycleTechnical DirectionArchitecture Governance

Tech Stack

Tools & technologies

CloudSDLC

About the role

Key responsibilities & impact

Set technology strategy and architecture direction for Engagement Technology
Drive target-state architecture across product, platform, and integration domains
Lead solution architecture for major initiatives
Drive architectural simplification and legacy retirement
Establish architecture governance and the design review process
Translate business strategy into technical direction
Serve as primary interface to Enterprise Architecture
Partner with AI Engineering, Data, Security, Infrastructure, and FinOps organizations
Represent the group in enterprise architecture forums
Own AI SDLC transformation, including tooling selection, pilots, scaling, standards, guardrails, secure usage patterns, adoption metrics, training, and change management
Own cloud migration strategy and execution roadmap
Define migration patterns and target cloud architecture
Provide executive visibility into cloud migration progress and cost
Lead and grow a high-caliber team
Mentor senior engineers and architects
Publish an endorsed target-state architecture and sequenced roadmap within the first six months
Establish an AI SDLC operating model across delivery pods with baselined adoption metrics
Accelerate the cloud migration plan with first waves migrated
Establish architecture governance as a routine part of delivery

Requirements

What you’ll need

7+ years related work experience in software engineering and architecture, including enterprise-wide scope for the Senior Director level
5+ years direct supervisory/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 in Computer Science, Engineering, or a related field, or additional related equivalent work experience; equivalent combination of education and experience considered
Must be able to travel to multiple locations for work
Sedentary work requiring up to 10 pounds of force occasionally

Benefits

Comp & perks

Medical, dental, vision, life and global travel health insurance
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
2 well-being days
Additional voluntary benefits
Comprehensive wellness program
Opportunities for incentive or commission compensation
Annual reviews with pay-for-performance considerations for base pay increases