Senior Director, Digital Operations & AI

Senior Director, Digital Operations & AI

Location: Remote

Reports To: Senior Partner and Chief Operating Officer

Team: Central Support

Employment Type: Full-time, Exempt

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About Bellwether

Bellwether is a national nonprofit that exists to transform education to ensure students furthest from opportunity achieve outcomes that lead to fulfilling lives and flourishing communities. We work hand in hand with education leaders and organizations to accelerate their impact, inform and influence policy and program design, and share what we learn along the way.

We are a remote-first team, and our work is national in scope, so our flexible working style allows our professionals to work where they have built their lives, which means Bellwether can hire the best person for each role, regardless of geography. This role can be based anywhere in the United States. Up to 15% travel may be required.

As Bellwether implements our new strategic plan, we will reimagine how we work, embrace emerging technologies, evolve our service offerings, and embed the processes and mindsets for learning across the organization. A key part of this transformation is harnessing the power of artificial intelligence (AI) to enhance how we operate, collaborate, and deliver value. Bellwether sees AI not just as a tool for efficiency, but also a strategic lever for insight generation, innovation, and rethinking how we deliver impact for the education sector.

WHY AI MATTERS AT BELLWETHER

AI is reshaping the education landscape and how organizations such as Bellwether can make a difference for the partners we support and, ultimately, the students, families, and communities we aim to serve. For us, AI represents an opportunity to:

• Inform and guide the sector in navigating the complex question of how AI affects learners, educators, and the systems and organizations working to improve education.
• Develop and integrate new tools and resources into our workflows, so that Bellwether can provide high-quality and effective support to more partners, extending our impact.
• Engage in organizational learning and knowledge sharing to continuously reflect on and improve how we work.
• Empower our team to focus on human-centered work by building robust, nimble infrastructure that enhances collaboration and frees them from routine tasks.

THE ROLE

This is a leadership role on Bellwether’s Central Support (CS) Team that balances strategic direction with hands-on execution. We anticipate the Senior Director will function similarly to a product manager with change management depth and technical range. This role is right for someone who can help shape the vision, run the roadmap, and build the work. Because this role does not come with a dedicated technical team, execution will occur through a mix of individual work, contracted support, and close partnership with other Central Support roles, depending on the project's requirements.

Here’s how we expect this role to spend its time:

• 35-40% Strategic direction and roadmap ownership : Translating the organization’s digital transformation and AI priorities into a sequenced, realistic plan and making clear-eyed calls about what to build, what to defer, and what to resist.
• 25% Client-facing delivery : Embedded support on select projects where AI integration, workflow design, or operations modernization supports Bellwether’s service offerings.
• 35-40% Hands-on execution : Building prototypes, configuring tools, writing automations, testing integrations, and designing systems that the Central Support team can maintain without ongoing technical support.

This role reports directly to Bellwether’s Chief Operating Officer (COO). It works in close partnership with the Senior Director of Enterprise Operations, who ensures what gets built can be successfully scaled and sustained across the organization. The role is a member of the internal AI Leadership Team and the AI Skunkworks team (the “Skunks,” the most advanced AI practitioners currently at Bellwether, holding a 20% time allocation), as well as the Central Support Leadership Team. Other AI-fluent team members will continue to contribute in a supporting capacity.

WHO YOU ARE

The right person for this role has spent a combination of 8+ years owning both strategy and execution in digital transformation, workflow redesign, or operations. You have hands-on AI and automation experience, and you have designed tools that bring lasting change. You think in systems, translate fluently from executive strategy to hands-on detail, and have built authentic adoption in cultures where enthusiasm was uneven and pushback was genuine. You're not a pure technologist who needs a team to execute, a strategist who doesn't build, or an AI evangelist without implementation depth: you lead through influence, not mandate .

WHAT YOU WILL DO

• Own the Transformation Roadmap

You will develop and own a sequenced roadmap grounded in what previous discovery has surfaced: prioritizing what Bellwether can absorb, sequencing what to build first, and saying no to what would distract from durable progress. You are the COO’s primary partner on this work, which means translating strategic intent into a plan that the organization can follow and the operations team can sustain.

• Develop and maintain the transformation roadmap; revisit and resequence as conditions change.
• Make prioritization calls and communicate them clearly across the organization
• Connect Skunks experimentation, internal cohort learning, and CS team needs into a unified direction.
• AI Leadership : in partnership with the AI leads, as well as the internal team leading Bellwether’s professional learning, help review and influence the design of learning pathways, support org-wide AI-fluency, and help move Bellwether from various stages of adoption to a consistent, AI-embedded practice.

• Lead Change in Digital Transformation

Bellwether has digital transformation and AI enthusiasts, skeptics, and people who are somewhere in between. This role must earn trust from all of them by demonstrating value before asking for adoption, listening before prescribing, and creating space for people to learn without letting that become an indefinite delay.

• Navigate a collaborative culture while still driving decisions and holding momentum
• Communicate technical work to nontechnical leaders; translate organizational complexity for technical implementers.
• Champion responsible AI adopt