Director, IT PMO and Vendor Management

The Baldwin Group•Tampa, FL

About The Position

The Director, IT PMO & Vendor Management provides strategic and operational leadership for Baldwin’s enterprise IT portfolio governance and vendor value management functions. This role is accountable for executing the firm’s technology investment and vendor strategies, leading a multi-disciplinary team that governs how Baldwin prioritizes technology initiatives, allocates resources across ~400 IT colleagues, and optimizes value and risk across a diverse ecosystem of 200+ technology vendors. Reporting to senior IT leadership, this role translates enterprise and technology strategy into a coherent multi‑year roadmap for portfolio governance and vendor management. Additionally, this role establishes and continuously improves standards, operating models, and analytics that enable executive decision‑making on portfolio mix, risk, and return on investment. Further, this role owns the integrated view of project, resource, and vendor spend, and is responsible for driving cost optimization, performance, and risk mitigation through both internal teams and external partners. The Director builds and develops a high-performing team of managers and senior professionals, manages the function’s budget, and partners closely with Finance, Procurement, Legal, Security, and business leaders to ensure technological investments and vendor relationships support firm‑wide objectives. Position Summary The Director, IT PMO & Vendor Management provides strategic and operational leadership for Baldwin’s enterprise IT portfolio governance and vendor value management functions. This role is accountable for executing the firm’s technology investment and vendor strategies, leading a multi-disciplinary team that governs how Baldwin prioritizes technology initiatives, allocates resources across ~400 IT colleagues, and optimizes value and risk across a diverse ecosystem of 200+ technology vendors. Reporting to senior IT leadership, this role translates enterprise and technology strategy into a coherent multi‑year roadmap for portfolio governance and vendor management. Additionally, this role establishes and continuously improves standards, operating models, and analytics that enable executive decision‑making on portfolio mix, risk, and return on investment. Further, this role owns the integrated view of project, resource, and vendor spend, and is responsible for driving cost optimization, performance, and risk mitigation through both internal teams and external partners. The Director builds and develops a high-performing team of managers and senior professionals, manages the function’s budget, and partners closely with Finance, Procurement, Legal, Security, and business leaders to ensure technological investments and vendor relationships support firm‑wide objectives.

Requirements

Proven leadership of PMO and vendor management functions, including responsibility for strategy, operating model design, and execution in complex, multi‑stakeholder environments.
Strong people leadership skills, with demonstrated success hiring, developing, and retaining high‑performing managers and senior professionals, and building a culture of accountability and collaboration.
Deep expertise in portfolio management, including demand/capacity planning, prioritization frameworks, benefits realization, and scenario analysis for complex, multi‑year technology roadmaps.
Advanced vendor management experience, including segmentation, performance management, contract lifecycle governance, and leading major negotiations for multi‑million‑dollar technology spend.
Fluency in technology finance and “CFO language” (business cases, ROI modeling, TCO, budgeting/forecasting, cost allocation, and commercial structures) and the ability to connect technology and vendor decisions to firm‑level financial outcomes.
High data and analytics acumen, with the ability to synthesize demand, cost, risk, capacity, and value information into clear insights and executive‑ready recommendations.
Strong understanding of enterprise technology environments, including how portfolio and vendor decisions affect architecture, infrastructure, security, and application roadmaps and service levels.
Experience operating in Agile and hybrid delivery environments, with familiarity in scaled agile frameworks (e.g., SAFe, LeSS) and their implications for governance and vendor models.
Exceptional communication and storytelling skills, capable of translating complex portfolio and vendor concepts into clear narratives for C‑suite, non‑technical stakeholders, and external partners.
Ability to influence without relying solely on authority, building alignment across executives, IT leadership, Finance, Procurement, Legal, and key vendors.
Change leadership capability, including designing and executing change plans, addressing resistance, and embedding new ways of working.
Bachelor’s degree in business, finance, information systems, or a related field required; advanced degree (e.g., MBA) strongly preferred.
12+ years of progressive experience in portfolio management, vendor management, technology finance, or related operational/financial disciplines, including:
Significant experience leading PMO and/or VMO functions at a department or multi‑team level.
Significant experience owning technology investment governance and vendor strategies for large, multi‑year portfolios.
Industry experience in insurance, financial services, or other highly regulated, complex environments preferred.
Relevant certifications (e.g., PMP, PgMP, SAFe, vendor management or procurement certifications) preferred.

Nice To Haves

advanced degree (e.g., MBA) strongly preferred.
Industry experience in insurance, financial services, or other highly regulated, complex environments preferred.
Relevant certifications (e.g., PMP, PgMP, SAFe, vendor management or procurement certifications) preferred.

Responsibilities

Own and direct the firm’s IT portfolio and vendor management strategy, aligning roadmaps, governance models, and success measures with enterprise and IT strategy.
Define and maintain enterprise portfolio governance for Agile, Waterfall, and hybrid delivery (e.g., demand intake, prioritization, stage gates, risk and dependency management, funding decisions, and value realization).
Establish and chair or co‑chair key governance forums (e.g., portfolio review boards, investment councils, vendor steering committees), ensuring timely, fact‑based decisions and clear follow‑through.
Set multi‑year goals and KPIs for portfolio performance, vendor value, and risk posture; regularly report performance and strategy progress to executive leadership.
Lead and develop a team of PMO and vendor management leaders and senior professionals; set clear objectives, manage performance, and build succession and bench strength within the function.
Integrate portfolio, financial, and vendor views into a single management framework that covers demand, capacity, spend, risk, and value across major programs and platforms.
Own the IT PMO & Vendor Management budget, including operating expense, capital investment tracking, and vendor spend aligned to portfolio priorities.
Standardize and oversee contract lifecycle management (intake, evaluation, approval, repository, renewals, and terminations) in partnership with Procurement, Legal, and Security.
Direct the design and operation of portfolio and vendor dashboards, ensuring executives have consistent answers to “What’s on track?”, “What’s at risk?”, and “Where is the money going?”.
Oversee enterprise portfolio planning and sequencing of strategic technology initiatives, balancing capacity, risk, interdependencies, and business value.
Review and approve business cases and investment proposals for major technology initiatives; ensure alignment with firm‑level financial targets and strategic outcomes.
Guide trade‑off decisions (start/stop/continue/resize) based on integrated analysis of cost, risk, benefit, capacity, and strategic fit; recommend investment shifts to CTO and senior leadership.
Ensure benefits realization plans, metrics, and accountabilities are in place and actively monitored for major investments.
Set the vendor strategy for key technology domains (e.g., infrastructure, applications, SaaS platforms, consulting and managed services), including preferred partner models and sourcing mix.
Direct vendor segmentation, scorecards, and performance management, including SLAs, KPIs, and joint improvement plans for strategic and critical vendors.
Oversee vendor spend analytics, forecasting, and scenario modeling to identify and execute consolidation, rationalization, and cost‑reduction opportunities while maintaining service quality and managing risk.
Lead or sponsor major vendor negotiations and renewals, ensuring commercial structures, service levels, and risk terms are aligned with Baldwin’s objectives.
Partner with Security, Risk, and Legal to embed vendor risk, compliance, and audit requirements into the operating rhythm and to remediate issues proactively.
Set the vision and standards for portfolio and vendor management tools (e.g., JIRA, Confluence, Airtable, vendor management platforms) and data models to support reliable reporting and insight.
Ensure data governance for portfolio and vendor data, including ownership, quality controls, and processes that improve accuracy and timeliness.
Sponsor automation and process improvements that streamline demand intake, approvals, contract management, invoicing, and reporting.
Serve as primary point of escalation for issues and decisions that cut across portfolio, finance, procurement, legal, security, and delivery teams.
Influence and advise senior business and IT leaders on portfolio mix, funding models, vendor strategies, and sequencing of major investments.
Drive adoption of pragmatic governance, ensuring processes and controls enable rather than hinder speed, transparency, and quality.
Lead change management for new portfolio and vendor practices, including communications, training, and coaching for project managers, product owners, and business sponsors.
Represent IT in firm‑wide forums related to investment planning, cost optimization, and strategic vendor relationships.