Director of Technology Strategy, Portfolio, Vendors & IT Finance

Sims Limited•Chicago, IL

About The Position

The Director, Technology Strategy, Portfolio, Vendors & IT Finance leads the Office of the CTO and serves as a strategic advisor and execution partner to the Chief Technology Officer. The role is responsible for translating business and technology strategy into an integrated roadmap, transparent investment portfolio, disciplined operating cadence, and measurable outcomes. The position brings together technology strategy, portfolio management, financial governance, vendor and commercial management, workforce planning, executive reporting and leadership-team operations. This is a hands-on leadership role. The successful candidate must be able to shape strategy and executive-level decisions while personally creating and operating the practical processes, data, dashboards, governance routines and solutions required to run the technology function effectively. Managed services partners will provide additional capacity and specialist support, but accountability for designing, implementing and operating these mechanisms remains with this role. The position will create a single, reliable view of technology priorities, demand, capacity, cost, risk, dependencies, and value. The role will help leadership make clear choices about where to invest, what to stop, what to simplify, and how to hold teams and partners accountable for delivery.

Requirements

Significant leadership experience in a global or complex technology organization.
Demonstrated experience across several of the following: technology strategy, portfolio management, technology financial management, vendor and commercial management, Technology Business Management, enterprise transformation, PMO or Office of the CIO/CTO leadership, and Chief of Staff responsibilities.
Experience personally building and operating practical governance, portfolio, financial, vendor or performance-management processes, rather than only providing policy or advisory oversight.
Experience developing executive-level strategies, roadmaps, business cases, dashboards and decision materials.
Strong understanding of technology operating models and the relationship between strategy, architecture, portfolio, delivery, service management, cybersecurity, finance and workforce.
Experience managing substantial technology budgets, investment portfolios, and vendor relationships.
Demonstrated ability to influence senior business and technology leaders without relying solely on formal authority.
Strong financial, commercial, analytical, written, and presentation skills.
Experience using internal teams and managed services partners to establish scalable operating capability.
Bachelor’s degree in technology, business, finance, engineering or related discipline, or equivalent professional experience.

Responsibilities

Partner with the CTO and technology leadership team to develop, maintain and communicate the global technology strategy.
Translate enterprise priorities into a coherent multi-year technology roadmap, annual operating plan, and prioritized set of initiatives.
Establish and continuously improve the global technology operating model, including decision rights, governance forums, accountability, and performance measures.
Coordinate strategic planning cycles and ensure alignment among business priorities, technology capabilities, financial constraints, workforce capacity and risk.
Lead strategic analysis on organizational design, sourcing, investment trade-offs, technology simplification and operating model improvements.
Track strategic commitments and ensure decisions are converted into clear owners, deliverables, and measurable outcomes.
Support the CTO in preparing executive, CEO, ELT, Board and Risk Committee materials.
Establish and personally operate the enterprise technology portfolio process across applications, infrastructure, cybersecurity, data, AI and major transformation programs.
Create and maintain a single source of truth for technology demand, approved initiatives, delivery status, investment, benefits, dependencies, risks and resource requirements.
Lead demand intake, business-case standards, prioritization, sequencing, and portfolio review.
Introduce consistent criteria for assessing strategic alignment, business value, risk reduction, regulatory need, architectural fit, delivery capacity, and total cost.
Facilitate portfolio decisions with the CTO and technology leadership team, clearly identifying proposed investments, trade-offs, constraints and initiatives recommended for delay or termination.
Monitor portfolio health and escalate delivery, financial, capacity, dependency or benefits-realization concerns.
Coordinate portfolio-level planning with business sponsors, Finance, Enterprise Architecture, Cybersecurity, Procurement and delivery leaders.
Build and operate decision logs, portfolio dashboards, executive reports and governance packs, using managed services support where appropriate.
Ensure portfolio governance does not replace the accountability of business sponsors, benefit owners, or delivery leads.
Own and operate the integrated technology financial-management process in partnership with Corporate Finance.
Coordinate annual budgeting, rolling forecasts, long-range plans, investment scenarios, and monthly financial reviews.
Establish transparent views of technology operating expenses, capital investment, project spend, committed costs, vendor spend and forecast variance.
Develop and maintain financial dashboards that connect cost with service, risk, capacity, business value and strategic outcomes.
Support business-case development and ensure consistent treatment of costs, benefits, funding sources, capitalization and benefits realization.
Identify opportunities for cost avoidance, simplification, demand management, contract optimization, application retirement and vendor consolidation.
Coordinate chargeback, allocation, or show back processes where applicable.
Provide the CTO and technology leadership team with early visibility of financial risks and required corrective action.
Build financial capability across technology leaders, so budget ownership is distributed rather than centralized solely within the Office of the CTO.
Establish and operate a strategic vendor-management framework for the technology function.
Maintain a consolidated view of major technology suppliers, contracts, renewal dates, commercial commitments, consumption, performance, risk and strategic importance.
Partner with Procurement, Legal, Finance, Cybersecurity and technology owners on sourcing strategies, negotiations, renewals and contract changes.
Lead commercial governance for the most significant technology vendors and outsourcing partners.
Develop and operate vendor scorecards covering service, delivery, cost, risk, innovation, contractual performance and relationship health.
Ensure vendor commitments are connected to technology roadmaps, financial forecasts, architectural direction and workforce plans.
Identify opportunities to consolidate suppliers, reduce duplicate services, improve commercial leverage, and address vendor concentration or continuity risks.
Coordinate executive vendor relationships and prepare negotiation positions for major commercial decisions.
Ensure third-party resources and managed services are governed through clear outcomes, accountability and performance measures.
Serve as a trusted advisor, thought partner, and execution partner to the CTO.
Run the operating cadence of the technology leadership team, including agendas, decision topics, pre-reads, action tracking and follow-through.
Connect discussions across strategy, delivery, finance, vendors, workforce, risk and organizational priorities.
Identify decisions that require CTO attention and resolve or redirect issues that do not.
Coordinate annual planning, quarterly business reviews, leadership offsites, town halls and organizational communications.
Maintain a consolidated view of CTO commitments, leadership-team actions, executive requests, and critical escalations.
Prepare concise, decision-oriented materials for senior executives and governance forums.
Lead selected cross-functional initiatives that do not fit naturally within a single technology tower.
Act as a constructive challenge to technology leaders, ensuring issues are surfaced early, and commitments are explicit.
Represent the CTO in agreed forums when appropriate, without displacing the accountability of functional leaders.
Help develop the technology leadership team and strengthen communication, collaboration, and execution discipline across the organization.
Build an integrated view of technology workforce capacity, critical skills, vacancies, contractors, managed services and future capability requirements.
Connect portfolio demand to available capacity and identify gaps before commitments are made.
Support leaders in evaluating build, buy, partner, automate and outsource options.
Coordinate strategic workforce planning with HR and Finance.
Establish consistent reporting on internal and external workforce costs and capacity.
Help ensure project funding includes appropriate delivery, architecture, change, security, and operational support capacity.
Monitor reliance on individual suppliers or scarce skills and recommend mitigation actions.
Support organizational design activity and role clarity across the technology function.
Define a balanced technology scorecard addressing business value, delivery, service, risk, cost, people, simplification and modernization.
Establish consistent measures and data definitions across the technology organization.
Create and operate executive dashboards and narratives that distinguish facts, risks, decisions and recommended actions.
Track strategic outcomes, delivery commitments, financial performance, benefits, and organizational health.
Ensure reporting is concise, decision-oriented and credible to the CEO, CFO, ELT and Board.
Build governance that improves decision quality without creating unnecessary bureaucracy.
Continuously assess whether governance forums, reports and processes remain useful and proportionate.