Senior Director, Head of AI & Architecture

The Baldwin Group•Tampa, FL

About The Position

The Senior Director, Head of AI and Architecture will lead the strategic vision, design, and execution of enterprise technology architecture and artificial intelligence capabilities across The Baldwin Group. This role is the firm’s primary driver in accelerating Baldwin’s transformation into an AI-driven organization, owning the design and deployment of an enterprise Agentic AI framework that enables autonomous, multi-step AI agents to operate across core business functions. The Senior Director serves as a trusted partner to executive leadership and business unit leaders reporting to the CTO-Retail, ensuring that data, platforms, and emerging technologies enable scalable growth, operational excellence, and differentiated client experiences. As a transformational technology leader, the Senior Director will advance the firm’s digital and AI maturity by aligning architecture strategy with business priorities, fostering innovation, and embedding enterprise standards that power long-term competitive advantage. This leader will be deeply fluent across leading large language model (LLM) ecosystems—including Anthropic Claude, OpenAI GPT, Google Gemini, and Meta LLaMA—and will drive the selection, governance, and optimization of the most appropriate models for Baldwin’s regulated, service-driven environment.

Requirements

Bachelor’s Degree in Computer Science, Engineering, Information Systems, or related field required; advanced degree preferred.
12+ years of progressive technology leadership experience, with demonstrated success in enterprise architecture, AI strategy, and digital transformation; including hands-on experience designing or deploying production AI/ML and LLM-based solutions.
Proven track record of leading complex, multi-platform environments and modernizing technology ecosystems at scale.
Proven experience designing and deploying Agentic AI systems capable of autonomous decision-making, multi-step task execution, and adaptive learning in enterprise environments.
Hands-on fluency with leading LLM platforms—Anthropic Claude (Sonnet, Opus), OpenAI GPT-4o, Google Gemini, and Meta LLaMA—with the ability to evaluate model fit, manage prompt engineering standards, and govern multi-model deployments.
Deep understanding of enterprise architecture frameworks, cloud platforms, data ecosystems, and cybersecurity principles.
Strong grasp of AI/ML capabilities, Agentic AI frameworks, LLM orchestration technologies (LangChain, AutoGen, Anthropic Agents SDK), and responsible AI governance.
Ability to translate complex technical concepts into clear business value and strategic outcomes.
Strong financial and operational acumen, with experience managing technology budgets and investment portfolios.
Exceptional communicator—engaging, genuine, and forthright—able to speak straight while fostering trust and alignment.
Collaborative enterprise leader who thrives in high-growth, fast-paced environments.
A growth mindset with grit and resilience—continuously turning today’s capabilities into tomorrow’s advantage.
Demonstrated ability to evaluate and select LLMs for enterprise fit—balancing capability, cost, data privacy, and compliance requirements—and to govern multi-model deployments across cloud and hybrid environments.
Ability to translate complex AI capabilities—including agentic systems, generative AI, and LLM-powered automation—into clear business value and board-ready strategic narratives.

Nice To Haves

Experience implementing AI, automation, and advanced data solutions in regulated or service-driven industries preferred.

Responsibilities

Partner with executive leadership to define and execute an enterprise AI and technology architecture strategy aligned with the firm’s mission, vision, and business basics—with a clear mandate to make Baldwin an AI-driven organization.
Scale with Vision: Align data, platforms, security, and enterprise systems to enable sustainable, efficient growth.
Serve as a catalyst for innovation and dreaming—advancing AI, automation, and emerging technologies that transform colleague and client experiences.
Translate business strategy into modern architecture roadmaps that prioritize value, agility, and resilience.
Design, deploy, and govern an enterprise Agentic AI framework—enabling autonomous, multi-step AI agents to orchestrate complex workflows across operations, client advisory, risk analysis, and compliance functions.
Lead evaluation and selection of LLM platforms—including Anthropic Claude, OpenAI GPT-4o, Google Gemini, Meta LLaMA, and Microsoft Azure OpenAI—based on performance benchmarks, data security, regulatory fit, and cost of ownership for Baldwin’s environment.
Establish and govern enterprise architecture standards across applications, data, integrations, infrastructure, and security.
Lead modernization of core platforms to ensure scalability, interoperability, and future-ready capabilities.
Drive alignment of technology ecosystems across business units to eliminate redundancy and enable seamless collaboration.
Ensure architecture decisions balance innovation, risk management, cost efficiency, and long-term sustainability.
Define and lead the enterprise AI strategy, establishing a clear vision for how artificial intelligence will transform colleague productivity, client experience, and business performance.
Identify, prioritize, and scale high-impact AI use cases across operations, client advisory, risk analysis, and workflow optimization.
Champion intelligent automation by integrating AI into core platforms, processes, and decision frameworks to streamline execution and reduce manual effort.
Establish responsible AI governance, ensuring ethical use, model transparency, security, and regulatory alignment.
Partner with business leaders to embed AI-powered insights into everyday workflows, enabling faster, smarter decision-making.
Oversee development and deployment of machine learning, generative AI, agentic systems, and advanced analytics solutions that create measurable enterprise value.
Enable foundational data readiness, governance, and accessibility necessary to support scalable and reliable AI solutions.
Lead a structured LLM evaluation and governance program—continuously benchmarking frontier models (Anthropic Claude Sonnet/Opus, OpenAI GPT-4o, Google Gemini, Meta LLaMA) against Baldwin’s use cases for accuracy, cost, latency, security, and compliance; define a multi-model strategy that avoids single-vendor dependency.
Build and scale AI platforms that support multi-agent orchestration, memory management, tool use, retrieval-augmented generation (RAG), and real-time feedback loops to power enterprise-grade agentic workflows.
Establish an AI Center of Excellence (CoE) to build organizational AI fluency, standardize development practices, and accelerate time-to-value for AI initiatives across business units.
Ensure reliable, secure, and high-performing technology environments that support enterprise operations.
Establish performance frameworks grounded in outcomes, continuous improvement, and real-time reflection.
Lead cross-functional integration of platforms, tools, and technical resources to maximize return on technology investments.
Partner with Finance and Technology leadership to ensure disciplined fiscal stewardship, portfolio prioritization, and measurable value delivery.
Serve as the connector between enterprise technology strategy and business unit execution.
Collaborate with business, product, data, cybersecurity, and infrastructure leaders to align priorities and roadmaps.
Drive accountability for enterprise standards through influence and governance in a matrixed environment.
Provide clarity, alignment, and architectural oversight to ensure teams are empowered while contributing to collective outcomes.
Model exceptional leadership by balancing vision with execution, recognizing strengths, and ensuring clarity of purpose across technology teams.
Foster a culture of accountability, collaboration, and continuous learning where colleagues thrive and put “We Before Me.”
Lead through the lens of The Baldwin Group’s values—Discerning, Grit, Genuine, Engaging, Purpose, and Dreaming while enabling innovation at scale.
Inspire and develop high-performing technology leaders and teams to deliver measurable business impact and Baldwin Alchemy—achieving more together than as individuals.