Senior Director, Digital Transformation

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 approximately 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 like Bellwether can make a difference for the partners we support and, ultimately, the students, families, 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 and the systems and organizations working to improve education.  
• Develop and integrate new tools and resources into our workflows, so that Bellwether to provide high-quality support to more partners, extending our impact.  
• Engage in organizational learning and knowledge sharing to continuously reflect on and improve how we work.  
• Build robust and nimble infrastructure that enhances collaboration and frees our team from routine tasks so they can focus on human-centered work. 
• Support the thoughtful adoption of AI in our work and in the sector, in alignment with our values. 

Our Senior Director of Digital Transformation will be at the forefront of making this vision reality, ensuring that AI adoption is thoughtful, ethical, and mission-aligned, ultimately strengthening our ability to drive educational opportunity for young people.

About the Position 

The Senior Director of Digital Transformation is a leadership position on the Central Support team, reporting to Senior Partner & Chief Operating Officer, DaWana Williamson. The Central Support team includes finance, business systems, operations, and human resources. Its purpose is to ensure that Bellwether’s program areas have the tools and services needed to serve our client partners and ultimately achieve Bellwether’s mission. 

A Strategic Role for a Transformative Moment  

We are seeking a forward-thinking, systems-savvy leader to guide Bellwether’s digital transformation, driving strategy and implementation of tools, technologies, and systems that deliver operational excellence and future-ready ways of working.  

This role will:  

• Partner across teams to unlock efficiencies and integrate emerging technologies, especially AI, as a catalyst for reimagining workflows, decision-making, and service delivery.  
• Serve as a bridge between AI experimentation and organization-wide adoption.  
• Ensure Bellwether’s digital evolution is bold, ethical, and aligned with our mission.   

This is a strategic and hands-on role, part designer, part builder, part coach. You’ll help distinguish high-value, people-intensive work from replicable, automatable workflows and architect solutions that shift the balance in favor of insight, impact, and mission.   

This new role will partner across teams to unlock efficiencies, integrate emerging technologies, and support the evolution of how we collaborate and deliver services.  

Responsibilities 

Modernize How We Work: Redesign Systems and Workflows  

• Lead digital transformation initiatives that align with Bellwether’s strategic priorities, integrating AI to drive efficiency and insight.  
• Evaluate and optimize existing systems (e.g., Salesforce, productivity tools, HRIS, etc.) to support modern, streamlined, impact-enhancing workflows.  
• Partner with the business systems and IT teams to ensure seamless implementation, integration, and usability of digital tools.  
• Collaborate with functional teams (e.g., Executive Assistants, People Operations, Finance, Business Systems, etc.) to design workflows that elevate human contribution.  
• Create systems that enable org-wide learning and embed knowledge management into workflows through tools and digital structures in partnership with internal teams. 

Champion AI and Digital Innovation  

• Identify and pilot opportunities for automation or AI enablement with a test-and-learn mindset.  
• Translating strategic experimentation into scalable internal practices that enhance operations.  
• Co-lead internal AI implementation, developing the systems and infrastructure that support org-wide fluency and adoption.  
• Partner with the AI Lead to ensure knowledge sharing and tool experimentation are integrated and operationalized.  
• Support modernizing service delivery models and the integration of AI and automation in consulting, research, and knowledge-sharing functions.  
• Champion responsible AI adoption ensuring initiatives are designed and implemented with a strong focus on safety, ethical use, transparency and alignment with organization values.  
• Promote critical evaluation of AI systems by leading with healthy skepticism, challenging assumptions, stress-testing outputs, and encouraging evidence-based validation.  
• Serve as a member of Bellwether’s AI skunkworks team, an internal team tasked with AI experimentation. 

Transform How We Deliver Impact  

• Collaborate with client-facing, field-facing, and internal teams to support the development of AI-enabled or digitally supported service offerings.  
• Participate in the design of new teaming and delivery models that reflect the integration of technology and human-centered practice.  
• Support Bellwether’s ambition to reimagine consulting, research, and analysis in an AI-informed future. 

Your Impact in the First 18 Months  

• Bellwether’s systems and workflows are measurably more efficient, integrated, and insight-rich.  
• Teams feel supported, not burdened, by technology, and new tools are adopted with confidence.  
• AI and automation are embedded thoughtfully across operations and strategy, guided by user-centered design and appropriate guardrails.  
• The Central Support team is recognized as a driver of innovation and strategic transformation, not just back-office support.  
• New delivery models and internal teaming structures reflect the integration of digital tools and future-ready practices. 

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. Candidates should also possess the following: 

Required:  

• 7–10 years of experience in digital transformation, systems innovation, business operations, or process improvement.  
• Experience implementing AI tools, automation platforms, Salesforce, or other enterprise systems.  
• Demonstrated success leading cross-functional, tech-enabled change initiatives.  
• Strong strategic thinking, project management, and change leadership skills.  
• Exceptional communication and relationship-building skills.  
• A fast and continuous learner who demonstrates intellectual curiosity. 

Preferred:  

• Experience in nonprofit, education, or consulting sectors.  
• Exposure to service design, human-centered design, or digital innovation methodologies.  
• Understanding of AI use cases in internal operations (e.g., document management, scheduling, workflow automation). 

To Apply 

Use your online application — a custom letter of interest and a current resume — to show us you have the skills listed here or why the skills you have are the ones we need. You should also use your application materials to clearly highlight ways in which your background and experience align with Bellwether’s mission, including our commitment to helping young people furthest from opportunity.  

Please address your letter of interest to DaWana Williamson, Senior Partner and Chief Operating Officer. This role has a priority application deadline of October 24, 2025. While we prioritize applications received on or before that date, we will review applications as we receive them until the position is filled. Note: Applicants must be authorized to work for ANY employer in the United States. We are unable to sponsor or take over sponsorship of an employment visa at this time.  

Bellwether is committed to providing equal opportunities. It is our policy to ensure that all individuals with whom we are in contact are not discriminated against based on age, race, ethnicity, color, disability, gender identity, gender expression, political viewpoint, marital status, national origin, religion, sexual orientation, or veteran status. Further, as described above, Bellwether is committed to building a diverse team and strongly encourages individuals from all backgrounds to apply.