Senior Applications, Data & AI Assessment Lead (Ref #: )

Job Description Job Description Estrada Consulting, Inc. is seeking a Senior Applications, Data & AI Assessment Lead to evaluate enterprise applications, information systems, data management practices, integration capabilities, and emerging technology opportunities within a municipal government environment. Location: Remote / Hybrid - Nantucket, MA Project Duration: Approximately 120 days, anticipated January-May 2027 Work Arrangement: Remote work with required onsite assessment visits to Nantucket Island.
Position Overview: The selected consultant will assess enterprise applications, business systems, data platforms, software lifecycle practices, digital services, and opportunities for modernization and responsible artificial intelligence adoption.
The consultant will document existing capabilities, identify gaps and redundancies, evaluate business and technical risks, and develop practical recommendations for application modernization, data governance, automation, and strategic technology investment.
Key Responsibilities:

• Inventory and evaluate enterprise applications, departmental systems, software licenses, databases, and related technology platforms.
• Assess application health, functionality, lifecycle status, vendor support, integration capabilities, and alignment with business requirements.
• Review business workflows, application dependencies, data flows, interfaces, and opportunities for process improvement.
• Evaluate data management practices, including data ownership, quality, accessibility, reporting, records management, and information governance.
• Assess GIS-related application dependencies, integration requirements, and data exchange capabilities.
• Identify redundant, obsolete, underutilized, or unsupported applications and recommend modernization alternatives.
• Review software change management, testing practices, application maintenance, and technology lifecycle management.
• Assess readiness for digital transformation, workflow automation, and resident-facing digital services.
• Evaluate approved or embedded artificial intelligence capabilities, including AI governance, data readiness, human oversight, access permissions, security risks, and operational support.
• Develop application capability maps, gap analyses, modernization recommendations, and potential AI use-case assessments.
• Conduct stakeholder interviews and application walkthroughs to document current conditions and desired business outcomes.
• Collaborate with infrastructure, cybersecurity, and governance specialists to identify cross-functional risks and dependencies.
• Prepare findings, estimated implementation effort and costs, investment priorities, and recommendations for a multi-year IT strategic roadmap.

Required Qualifications:

• Demonstrated experience conducting enterprise application, business systems, or technology portfolio assessments.
• Strong knowledge of enterprise application architecture, system integration, databases, and information management.
• Experience evaluating business workflows, application functionality, technology dependencies, and modernization opportunities.
• Experience conducting business analysis, requirements assessments, data analysis, or enterprise technology reviews.
• Working knowledge of data governance, information quality, reporting, and application lifecycle management.
• Familiarity with AI capabilities, responsible AI assessment considerations, and related data and security risks.
• Strong stakeholder interviewing, analytical, documentation, and executive reporting skills.
• Ability to develop actionable technology recommendations aligned with organizational priorities.
• Availability for required onsite work in Nantucket, Massachusetts.

Preferred Qualifications:

• Previous experience evaluating municipal, county, or other public-sector enterprise applications.
• Experience with application portfolio management, enterprise architecture, GIS integration, and digital government services.
• Familiarity with Microsoft Power Platform, cloud applications, data analytics, or enterprise integration technologies.
• Experience evaluating AI use cases, automation opportunities, data readiness, and AI governance practices.
• Relevant enterprise architecture, business analysis, data management, cloud, or AI professional certifications.
• Experience preparing application modernization roadmaps, cost estimates, and executive-level strategic recommendations.

Work Location and Travel Requirements: This position is primarily remote with mandatory onsite assessment work on Nantucket Island. Candidates must be available for two separate onsite periods of approximately two weeks each, anticipated during project Weeks 3-4 and Weeks 9-11. Exact schedules will be coordinated with the project team. Candidates are not required to reside on Nantucket.