In A Nutshell
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.
Responsibilities
- 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.
- 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.
Skillset
- 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.
