AI Enablement Manager (Reproductive Healthcare - 12 month fixed term)

Upstream USA•Boston, MA

2d•Remote

About The Position

Upstream is scaling its use of AI across the organization, including in program delivery, practice transformation, partnership success, development, finance, marketing, communications, and within the technology team. This is a hands-on, forward-deployed role reporting to the Director of Data, Analytics and Technology (DAT). The AI Enablement Manager will embed directly with teams to understand their workflows, identify AI opportunities, build solutions, and support their adoption and measurement. This role involves discovering and prioritizing use cases, prototyping and delivering practical tools, developing AI fluency training, and leading evaluations, guardrails, and cost stewardship for responsible AI implementation.

Requirements

Bachelor's degree in a related field, or equivalent professional experience.
5+ years of experience in analytics, technology, internal tools, business process improvement, automation, consulting, or a closely related field.
Hands-on experience delivering AI or automation solutions in a business setting.
Demonstrated hands-on ability to build with modern AI tooling, including LLM platforms (e.g., Claude, ChatGPT), prompt and skill development, agentic workflows, and automation or low-code/no-code platforms.
Proven track record translating ambiguous business needs into practical, working solutions and moving from problem discovery to a usable result quickly.
Experience developing and delivering training, documentation, or enablement programs that changed how people work.
Comfort working with data from multiple systems, both structured and unstructured.
Fluency with SQL or equivalent for independent data investigation and validation.
Excellent written and verbal communication skills, including the ability to explain technical concepts to non-technical colleagues and present to senior leadership.
Ability to build trust and influence without direct authority across all organizational levels.
Self-directed and highly organized, with the judgment to manage multiple concurrent initiatives and prioritize in a fast-moving environment.
Ability to identify and leverage generative AI tools to streamline workflows, automate tasks, and enhance output quality while maintaining human checkpoints.
Proficiency in crafting effective prompts for desired outcomes and critical thinking skills to audit and refine AI-generated content.
Foundational understanding of ethical AI implications, including data privacy, bias recognition, and responsible use of company information.
Demonstrates the ability to remain focused, adaptable, and solution-oriented in the face of challenges, setbacks, or ambiguity.
Resilient, approaches obstacles with a growth mindset, and maintains commitment to goals under pressure.
Comfortable participating in an on-camera culture during meetings for connection, engagement, and collaboration.

Nice To Haves

Prior experience in an AI enablement, AI operations, internal tools, forward-deployed, or other business-embedded technical role.
Experience in a nonprofit, healthcare, or mission-driven organization, including familiarity with PHI and sensitive-data handling.
Familiarity with Upstream's core systems (Salesforce, Snowflake, dbt, Power BI, Asana, Google Workspace, Slack).
Working knowledge of APIs, connectors, MCP, or scripting in Python or a similar language.
Experience standing up enablement programs, champions networks, or internal knowledge bases.
Experience evaluating vendors and managing software licenses, usage tracking, or cost models.
Experience partnering with security, privacy, or compliance colleagues to evaluate technology.
A point of view on where AI does and does not belong, informed by experience.

Responsibilities

Embed with teams to understand end-to-end workflows, undocumented processes, and manual work to identify, scope, and prioritize AI and automation opportunities.
Translate ambiguous business problems into clearly defined use cases, solution hypotheses, and build plans, recommending against AI when simpler solutions exist.
Design, build, test, and deploy practical AI-enabled solutions (prompts, skills, agents, automations, lightweight applications) using approved AI tools and enterprise data.
Prototype rapidly, gather user feedback, and iterate on solutions.
Build and curate a reusable library of prompts, skills, templates, and workflow components.
Partner with DAT colleagues to transition validated prototypes into supported, production-ready solutions.
Document solution requirements, configurations, operating procedures, and expected outcomes.
Develop and deliver Upstream's AI training program, including workshops, office hours, and self-paced content.
Create and maintain user-facing resources such as documentation, quick-start guides, and best practices.
Cultivate a network of AI champions across departments to drive adoption.
Surface and share AI implementation successes, including quantified time savings and lessons learned.
Support change management for new AI tools and ways of working.
Serve as an internal subject matter expert on AI and automation tools.
Evaluate emerging AI tools and platforms, recommending adoption or decline.
Partner with DAT, Finance, and Contracts on AI tool license administration, cost tracking, and renewal planning.
Help establish and maintain practical guardrails for data privacy, PHI handling, appropriate use, and human review.
Define and track success metrics for AI initiatives, reporting progress to leadership.