Principal, Strategic Transformation

Principal, Strategic Transformation

Remote - United States

About the Role

Blackboard is evolving. We are the originator of the learning management system, and our next chapter will redefine it. That requires a set of cross-functional changes our competition avoids: operating model, cost structure, systems consolidation, and how artificial intelligence changes every aspect of how we work. The Chief of Staff owns that agenda with the executive team.

This role makes it run. You will build and hold the picture of what is happening, through relationships as much as documentation. You will keep the operating rhythm honest, do the analysis behind the decisions, and stay on the follow-through until the work is done.

You will do all of it with artificial intelligence as your toolbox. We expect you to understand what we need deeply enough to build it yourself, in weeks rather than quarters, and to set the pace for the rest of the company.

Why the Role Exists

Transforming a business takes insight and fortitude. We must make decisions and drive quick action. There is more on the list than we can do at once, and without someone with the insight to force strategy-aligned prioritization, where we want to go stays on the horizon instead of becoming how we work.

We are building the next evolution of Blackboard and we intend to do it quickly. Our strategy is clear. Making it true is a matter of ruthless prioritization and follow through, week after week. This job ensures that change.

What You Will Do

• Hold the global view. One defensible picture of initiatives, progress, purpose, and routes to success. Not a list of tasks, but expert understanding of what is ahead of us on the next leg of the journey.
• Run the rhythm. Ensure transformation work is well run: agenda, materials, the choices that actually need a decision, and the mechanics of keeping momentum. Capture, drive, push, and chase until it is done.
• Do the analysis. Baselines, business cases, and benefit tracking, built with Finance and defensible to them. When an initiative is drifting from what it promised, you find it in the numbers first.
• Carry assigned workstreams. Where the Chief of Staff needs something driven directly, you take it end to end: diagnose, design, deliver, measure. Expect one or two at a time alongside the standing work.
• Surface what is uncomfortable. Duplication, slippage, unowned work, and risks that are still small. Bring them early and bring them with evidence.
• Drive our evolution. Find the places in the business that deserve rethinking, and build the tools that let others come with us. You will write agents, automations, and internal applications yourself rather than filing requests for them. When a better way to work exists, find it and bring it in.

What Success Looks Like

• First two weeks. A first read on the portfolio: what is running, who owns it, and where each piece actually stands. You have met a wide swath of the team, including initiative owners, and they know why you called. One honest observation delivered to the Chief of Staff that we had not already made ourselves.
• First month. A complete and defensible baseline: what is running, what it costs, what it was supposed to deliver, and how far along it truly is. Reviews on a predictable rhythm with materials that arrive before the meeting. Your first recommendation on what to stop or sequence differently. At least one working tool you built to make this job faster. The baseline should not be maintained by hand.
• First year. Leadership relies on your view of the portfolio without checking it against three other sources. Decisions get closed rather than repeated, and benefit tracking runs against baselines Finance has signed off on. The way you work with artificial intelligence has been picked up by teams outside this office. You are not only executing the strategy. You are bringing us what should come next, and we are taking it seriously.

Required Skills and Experience

• You believe ownership is a first principle in everything you do.
• You work natively with modern artificial intelligence tools, not as a curiosity but as how you actually work. You have built things with them: agents, automations, analyses, internal applications. Tell us what you built, what it replaced, and whether anyone else uses it.
• You have run complex cross-functional work in an organization where nobody reported to you, and you can describe what shipped.
• You are comfortable in a spreadsheet and in front of executives.
• You write clearly and briefly.
• You follow through without being reminded. The unglamorous half of this job is the half that matters.
• You are steady when priorities shift, and you say so plainly when something is not working.
• Fluency in written and spoken English. 

What We Are Not Looking For

Someone who tracks status without understanding the work. Someone who needs a title to be listened to. Someone waiting for a team before they will take ownership of anything. Someone who treats artificial intelligence as a topic rather than a tool to build with.

About Blackboard

Blackboard is a leading EdTech company and SaaS provider that delivers the digital environment for transformational teaching and learning. We serve thousands of institutions with the industry's most AI-advanced LMS, Blackboard Ally for accessibility, and institutional effectiveness solutions that put educators and learners at the center. We're an education company that builds technology. Learn more at blackboard.com.

The expected salary range for this position is $154,000 - $190,000. The range reflects base salary only and does not include additional compensation such as company bonus or benefits. Placement within the pay range will depend on a variety of factors, such as experience, skills, internal parity, and location.

Candidates must be legally authorized to work in the country where the role is based at the time of hire and must maintain that authorization for the duration of employment. The company does not provide visa sponsorship or immigration support for this position.

This job description is not designed to contain a comprehensive listing of activities, duties, or responsibilities that are required. Nothing in this job description restricts management's right to assign or reassign duties and responsibilities at any time.    

Blackboard is an equal employment opportunity/affirmative action employer and considers qualified applicants for employment without regard to race, gender, age, color, religion, national origin, marital status, disability, sexual orientation, gender identity/expression, protected military/veteran status, or any other legally protected factor.