AI Transformation Strategy Senior Director

Vertex Inc.•Boston, MA

1d•$227,200 - $340,800•Hybrid

About The Position

At Vertex, we continue to invest in a future-ready workforce where AI helps people strengthen expertise, improve decision-making and create greater impact for our people and patients. We are looking for a Senior Director, AI Transformation Strategy to help prioritize and coordinate the portfolio of big bets we are making to reinvent our most important workflows with AI. Reporting to the VP, AI Transformation, you will lead the enterprise portfolio strategy for Vertex’s AI transformation by prioritizing, sequencing, and tracking the portfolio of reinvention projects, to ensure we scale responsibly and strategically. You will provide senior leaders with a clear, real-time view of the whole portfolio, so they can see how reinvention projects are progressing, where progress is at risk, and where to accelerate, pause, or resequence. This includes building the models, frameworks, and reporting that support enterprise decisions, aligning teams and navigating dependencies, and partnering closely with Finance, AI Transformation Operations, Workforce Strategy & Innovation, Data Technology & Engineering, and functional leaders to keep the portfolio focused, current, and tied to real business value. To succeed, you will bring clarity to a portfolio of deeply connected projects across teams, providing a shared, evidence-based view of progress, dependencies, and decisions. You will model responsible use by continuously learning, applying AI to innovate your own work, and championing practices that create value.

Requirements

Deep knowledge of enterprise portfolio strategy, investment governance, prioritization, sequencing, and portfolio-performance management.
Strong analytical and strategic-thinking skills, including the ability to integrate incomplete or competing information into clear, evidence-based recommendations.
Strong financial and business acumen, including the ability to interpret value cases, investment assumptions, capacity constraints, and portfolio-performance evidence.
Ability to identify and evaluate interdependencies across projects, functions, resources, timelines, and strategic priorities.
Ability to build and interpret portfolio models, scenarios, decision frameworks, and executive-level portfolio views.
Excellent executive communication and data-storytelling skills, with the ability to translate complex portfolio evidence into concise choices and recommendations.
Strong cross-functional influence and alignment skills, particularly across Finance, Workforce Strategy & Innovation, Data Technology & Engineering, AI Transformation Operations, and business functions.
Practical fluency with AI tools and emerging AI capabilities, with the ability to apply AI responsibly to research, analysis, scenario development, and portfolio insight.
Ability to operate effectively as enterprise priorities, evidence, technology, and external conditions evolve.
Bachelor’s degree in business, finance, strategy, economics, engineering, analytics, or related field – or relevant experience
Typically requires 12 or more years of experience in enterprise portfolio strategy, corporate strategy, strategic finance, investment governance, or transformation strategy, or the equivalent combination of education and experience.
Demonstrated experience developing recommendations for prioritizing and sequencing a complex portfolio of enterprise investments or transformation programs.
Experience designing or facilitating portfolio governance and supporting senior leaders through consequential investment, prioritization, or resource-allocation decisions.
Experience integrating strategic, financial, operational, workforce, risk, and delivery evidence into a coherent portfolio view.
Experience developing scenarios, portfolio models, and executive recommendations that clarify choices, implications, and interdependencies.
Experience advising senior executives and building alignment across functions with different priorities, constraints, and perspectives.

Nice To Haves

Advanced degree preferred.

Responsibilities

Maintain a single, current view of Vertex’s AI transformation portfolio, including each project’s purpose, scope, status, timing, expected value, readiness, risks, and key dependencies.
Develop recommendations on which reinvention projects should move forward and how they should be sequenced based on strategic importance, expected value, readiness, risk, dependencies, and organizational capacity.
Design and facilitate a consistent process for reviewing investments and supporting decisions to accelerate, pause, resequence, or stop work.
Identify and navigate the dependencies across projects, teams, timelines, and resources, and adjust sequencing as those dependencies shift.
Build alignment among project sponsors, functional leaders, and key partners so priorities, responsibilities, decisions, and expectations remain clear across the portfolio.
Give senior leaders a concise, evidence-based view of portfolio progress, emerging risks, and upcoming decisions, along with the scenarios, portfolio models, and recommendations they need to weigh competing priorities and decide with confidence.
Partner with Finance, Data Technology & Engineering, Workforce Strategy & Innovation, AI Transformation Operations, and functional leaders to connect portfolio priorities with available funding, resources, delivery capacity, and workforce readiness.
Regularly refresh the portfolio as business priorities, evidence, technology, and external developments change, keeping Vertex’s AI transformation focused on the opportunities with the greatest potential value.