Head of Portfolio & Delivery and Chief of Staff

Head of Portfolio & Delivery and Chief of Staff
Hybrid / Dallas, TX
Perm Role
Travel Required: Minimal to moderate – 10–20%

Our client is seeking a leader for a dual-mandate role in the Office of the CTO.

As Head of Portfolio & Delivery, this leader owns how technology work enters, is prioritized, is governed, is delivered and is proven across the client’s two businesses, and the corporate functions that support them: the single intake, the portfolio view, the Digital Delivery Program as a permanent function, delivery and change standards, the technology scorecard and capitalization evidence.

As Chief of Staff to the CTO, this leader runs the operating cadence of a technology organization of roughly 200 people and extends the CTO’s reach: preparing decisions, closing loops, carrying the CTO’s intent into forums the CTO cannot attend and bringing back what the CTO needs to hear.

The Chief of Staff mandate builds over the first six months as the leader earns a network inside our client, and gives the function executive access and the authority to hold the organization to its commitments.

The role is accountable for the delivery system and the leadership system, not for product priority: business technology leaders and their product managers own what is built and in what order; this leader owns how it gets in, how it gets done, how its value is proven and how the CTO’s leadership team runs. Portfolio & Delivery is a permanent function; the Digital Delivery Program is the process that guides it.

Responsibilities:

• Design and run the CTO’s operating cadence: weekly leadership team meeting, monthly business reviews with each of the CTO’s direct reports, quarterly business reviews with the COO, CGO and CFO organizations, strategic technology planning sessions with business partners (twice per year) and the annual planning and budgeting cycle; own agendas, pre-reads, decision logs and follow-through.
• Prepare the CTO for Executive team, board and Technology Investment Committee sessions: frame the decision, assemble the evidence, pressure-test the recommendation and draft the materials to executive standard; own the technology sections of board and Leadership packs.
• Act as the CTO’s proxy where delegated: attend forums on the CTO’s behalf, represent the CTO’s position accurately, capture commitments and escalate only what requires the CTO; never trade on borrowed authority.
• Manage the flow of issues into and out of the CTO’s office: triage requests from the  Executive Leadership, the business functions, and the technology organization, resolve what can be resolved at the right level and bring the CTO the decisions that are genuinely the CTO’s to make, with options and a recommendation. The standard is access made more productive, not access controlled: the CTO’s direct reports and Executive Leadership peers keep a direct line to the CTO, and this leader is measured on whether they experience the Office of the CTO as easier to work with.
• Own internal communication for the technology organization with the CTO: all-hands narratives, leadership team communications, change messaging for the operating model and the workforce plan, and the CTO’s written voice to the organization.
• Lead confidential and special projects for the CTO, including workforce and organization design, leadership hiring support, vendor and MSP rationalization and IPO-readiness preparation, with the discretion these require.
• Serve as an honest counsel to the CTO: tell the CTO what the organization is saying, where a plan is not landing and where the CTO’s own decisions or behavior are working or, alternatively, are creating friction, privately and early. Portfolio and Intake
• Stand up and run the single technology intake for every request from the businesses and corporate functions (projects, enhancements, AI use cases and small changes), triaged within five business days into a delivery lane: pod, program, vendor implementation or the 30-day Sustainment fast lane.
• Maintain one portfolio view across  business areas with visible status, dated slots and capacity by funding lane (Run, Grow, Transform, Protect); eliminate side-door demand and escalation as a route to capacity.
• Track success metrics by project, including actual cost, realized benefit, and key project KPI’s
• Serve as secretary to the Technology Investment Committee: quarterly capacity allocation proposals, business cases above threshold and the operating model scorecard; track decisions and follow-through. Facilitate the twice-yearly Strategy Alignment Sessions with the COO, CGO and CFO organizations.
• Own the technology spend and capacity baseline (roles, contracts and licenses tagged to a lane and a business) and the annual guardrails set from it, in partnership with Finance.
• Co-own AI opportunity triage with the Head of AI Enablement so that AI use cases enter through the same intake, are scored against the same lanes and are routed to the AI Center of Excellence, a pod or Sustainment on the same five-day standard; hold architecture governance to standards set by Enterprise Architecture.

Digital Delivery Program and Delivery Standards

• Lead the Digital Delivery Program as a permanent function: install, then run, the enterprise delivery system across four lanes (AI-native pods, programs, vendor implementations and Sustainment) with common gates and a benefit review at close.
• Set and enforce the delivery standards program and project managers follow for plan, budget, risk, release and change management and capitalization evidence; own the application ownership register with a named business and technical owner for every application.
• Coordinate programs that span multiple pods and vendors (cloud migration, contact center, Workday releases) through the Senior Program Managers; hold vendor implementations to the standard that the client owns requirements, data, integration and adoption.
• Build and publish the operating model scorecard and the monthly delivery scorecard to the Technology Councils and the Executive Leadership: benefits realized versus committed, share of demand through intake, Sustainment SLA attainment, pods at velocity, cycle time from approval to release, contractor share and business partner NPS.
• Run value tracking end to end with Finance: establish baselines, ensure business ownership, conduct regular benefit reviews after release.
• Own capitalization evidence for technology projects in partnership with Accounting.
• Build and lead Portfolio & Delivery: Senior Program Managers and Portfolio & Delivery Analysts
• Develop a team fluent in AI-assisted delivery and reporting and hold every team member to the client’s AI-readiness threshold. Knowledge, Skills, and Abilities Portfolio, PMO and Transformation Office
• Demonstrated success standing up or leading a transformation office, enterprise PMO or portfolio function in a large, multi-business organization, including intake, prioritization, capacity allocation and executive reporting.
• Expertise in portfolio funding models (capacity or lane-based funding versus project-by-project), business case and benefit tracking, and technology spend baselining.

Executive Operations and Chief of Staff

• Experience running the operating cadence of a senior executive or a large function: agendas, pre-reads, decision logs, follow-through and executive communications; prior chief of staff, strategy office or management consulting experience strongly preferred.
• Board and  Executive Leadership -grade written and verbal communication; able to translate delivery detail into the language of business outcomes. Modern Delivery and AI-Native Development
• Deep knowledge of modern delivery frameworks (agile, product-based delivery, DevOps, CI/CD) and experience scaling persistent cross-functional teams and delivery pods.
• Working understanding of AI-assisted software development (for example Claude Code, copilot tooling, evaluation harnesses) and of how it changes team shape, velocity and cost. Value, Metrics and Financial Fluency
• Ability to define and run benefit realization with Finance, including baselines, 90-day and 12-month reviews and public-company controls; familiarity with software capitalization (ASC 350-40) evidence requirements.
• Strong data discipline, builds scorecards executives act on from software delivery management systems, financial and vendor data.

Education & Experience:

• Bachelor’s degree in Business, Computer Science, Information Systems, Engineering or a related field required; MBA or equivalent advanced degree preferred.

• 12+ years of progressive experience in technology delivery, portfolio management, strategy or transformation leadership, including 3+ years leading an enterprise PMO, transformation office or portfolio function reporting to a CIO/CTO or COO.
• Prior experience as chief of staff, head of a strategy or transformation office, or engagement manager in a top-tier management consultancy strongly preferred.
• Direct experience implementing a portfolio and delivery operating model across multiple business units required; experience with capacity-based or lane-based funding models preferred.
• Automotive, insurance, multi-site services or retail industry experience a plus; public-company or IPO-readiness environment a plus.

Measures of Success In Three Months:

• The CTO’s leadership cadence is running with published agendas, pre-reads and a decision log by 90 days; Executive Leadership and board materials are delivered to standard with no rework by the CTO.
• All technology demand flows through the single intake, with five-business-day triage, by the end of March 2027).
• Technology spends and capacity baseline delivered and FY27 lane guardrails set from actuals; Technology Investment Committee operating on a quarterly cadence. In six months:
• Sustainment (maintenance and small enhancements) SLA met (90% of approved changes delivered within 30 days) for two consecutive quarters; zero applications without a named business and technical owner.
• Operating model scorecard reported quarterly to the Executive Leadership  and feeding the board AI value review; every released initiative has a benefit review on file. In one year:
• Strategy Alignment Sessions held on to schedule with a single strategic technology roadmap presented to the Executive Leadership .
• Positive business partner NPS by end of 2027; the CTO’s direct reports and Executive Leadership  peers rate the Office of the CTO as making their work easier and report no loss of direct access to the CTO. Certifications, Licensures, and Language Skills (If needed)
• PMP, PgMP, SAFe (RTE/LPM), Lean Portfolio Management or equivalent experience strongly preferred.

• AI Practitioner or AI Product Management credential or demonstrated equivalent hands-on experience with AI-assisted delivery, a large plus.

What Makes This Person a Strong Chief of Staff:

• Low ego, high ownership. Influence comes from the CTO’s and the organization’s trust, not from title.
• The right candidate is comfortable doing consequential work that others get credit for and is energized by making the technology team more effective rather than by personal visibility.

• Discretion by reflex. Handles workforce, compensation, vendor, board and IPO-sensitive information as a matter of course. Knows what to share, with whom and when.
• Anticipates and finishes. Sees around corners: spots the meeting that will go badly, the decision that is drifting, the stakeholder who has not been heard, and acts before the CTO has to. Closes every loop; nothing handed to this person is heard about again unless it needs to be.
• Candor upward, alignment outward. Tells the CTO the truth, especially when it is unwelcome, and does it privately, early and with a proposed course of action. Then, once a decision is made, carries it into the organization as their own.
• Faithful translator, not a free agent. Can hold the CTO’s intent in their head and reproduce it faithfully in rooms the CTO is not in; equally able to say “I don’t know what the CTO would want here, let me find out” rather than guess.

• Comfortable at every altitude. Moves in one day from a board pre-read to an intake triage to a difficult conversation with a program manager and is credible at all three altitudes.
• Sees technology organization as a system of people, cadences, incentives and information flows and fixes the system rather than the symptom.

• Calm, fair and easy to work with. Steady under pressure and even-tempered with people who are not; disagreement does not become personal. Peers on the CTO’s leadership team and in the business experience this person as a fair broker who makes the CTO’s office easier to work with, not a gatekeeper.
• Exacting communicator. Writes and speaks with precision and economy: a one-page brief, a crisp decision memo, an all-hands narrative that sounds like the CTO. Catches the wrong number, the wrong name and the wrong framing before anyone else sees it.
• Reads the room and builds the network. Reads the Executive Leadership Team, the business and the technology organization accurately, adapts approach to the person in front of them and builds relationships across the COO, CGO, CFO, CHRO and General Counsel organizations that the CTO can draw on.
• Structured in ambiguity, hungry to grow. Comfortable with ambiguity and with being handed a problem rather than a task; structures it, finds the owner, sets the path and reports back. Growth-minded about the role itself, understands this is a two-to-three-year seat that prepares them for a broader technology or business leadership role at the client company.