Bellwether
Senior Director, Digital Operations & AI
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Senior Director, Digital Operations & AI
Location: Remote Reports To: Senior Partner and Chief Operating Officer Team: Central Support Employment Type: Full-time, Exempt
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.
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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 adoption grounded in ethical use, transparency, appropriate guardrails, and alignment with Bellwether's AI policy and values.
- Contribute to professional learning opportunities that support team adoption of new tools and processes.
- Lead people through change with strategic clarity, humility, and care.
Build, Not Just Plan
This is a hands-on role. You will design workflow prototypes, configure tools, write automations, and test integrations, modeling what excellent digital practice looks like in day-to-day work. Every system you build must be operable by the people who use it.
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- Identify and redesign high-friction workflows across CS, External Relations, and program-facing functions (grant management, data and reporting, knowledge management, executive coordination).
- Integrate AI where it adds durable value, not where it is merely possible; apply a test-and-learn mindset.
- Evaluate existing systems (Salesforce, Human Resource Information Systems, project management tools, productivity platforms) for gaps, integration opportunities, and AI-enabled enhancements in partnership with the Business Systems team.
- In partnership with the Knowledge Sharing Lead, build knowledge management infrastructure that captures institutional knowledge and survives staff transitions.
- Design for data privacy and security by making deliberate calls about what data can flow to which systems, where AI tools introduce exposure, and how to build within Bellwether's confidentiality obligations to clients and staff.
WHAT SUCCESS LOOKS LIKE AT 12 MONTHS
- Three to five high-friction workflows redesigned, adopted, and producing measurable value and impact.
- AI use is embedded in how Central Support teams do core work (not merely available as a tool, but integrated into workflows and deliverables).
- Trusted relationships built across the organization with the advanced builders, novice learners, heavy skeptics, busy practitioners, and leaders who need to make org-wide decisions.
- Systems are documented, maintainable, and operable by the Business Systems team.
- Begin contributing as a strategic thought partner on a small number of client-facing or externally oriented projects, as staffed by the organization based on portfolio needs and your expertise.
QUALIFICATIONS
Competitive candidates for this role will demonstrate a passion for our work and content expertise. To be successful, candidates must have strong organizational, problem-solving, communication, and project management skills. They should also possess the following:
Required
- 8+ years in digital transformation, workflow redesign (process engineering), operations, or product management in a role that required owning both strategy and execution, not just one.
- Demonstrated track record of leading organizational change and building lasting adoption in contexts where enthusiasm was uneven and pushback was genuine.
- Hands-on AI and automation experience: you have built workflows, configured tools, and implemented AI in real operational settings that improved effectiveness and sustainability.
- Technical understanding of generative AI: you think in terms of evaluation, context engineering, and agentic design, and you can balance trade-offs among speed, latency, cost, and quality.
- Systems thinking: you map workflows end to end, find where friction lives (not just where it is most visible), and design for root causes.
- Ability to assess data privacy and security risks: you anticipate the privacy and security risks that come with AI adoption, translate those for the wider team, and design/build with mitigating them in mind.
- Communication range: you translate fluently across every level of the organization, from executive strategy conversations to the hands-on details of getting work done.
- A builder's attitude: you have shipped things, owned deliverables, and know what it feels like to be accountable for a system people rely on.
- Strong mission orientation: you understand why Bellwether's work matters and can connect better internal systems to better outcomes for young people.
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