Senior Vice President/Vice President, Product

About the Role

The SVP/VP, Product will lead the design, development, and deployment of SkillUp’s next-generation agentic AI-centric platform — one that deploys agentic-AI capabilities to deliver actionable insights, personalized career guidance, and seamless connections to opportunity. This leader will drive an ambitious roadmap that blends technical innovation and partnerships with real-world impact, ensuring our solutions are ethical, human-centered, and measurable. You are a strong fit for this role if you are looking to join an entrepreneurial team and excited about integrating new technologies, rapidly prototyping, leveraging partners, and scaling impact within a small nonprofit.

Key Responsibilities

Product Strategy & Vision

• Define and execute the long-term product vision to position SkillUp as the leading platform for AI-powered career navigation for non-degree workers.
• Lead the strategic vision and execution of the organization’s product portfolio, ensuring all tools advance equitable access to career navigation and upskilling opportunities.
• Lead strategy for integrating agentic AI capabilities into the platform to enhance personalization, curation, and user guidance.
• Build and mentor a cross-functional product organization that integrates technology, research, and community voice to deliver accessible, high-impact experiences.
• Establish frameworks for evaluating ROI and social impact of product initiatives to inform funder engagement and future investment decisions.

Product Development & Execution

• Oversee end-to-end product lifecycle—from concept to launch to iteration—anchored in data insights, user feedback, and measurable impact outcomes.
• Manage and align a remote contracted development team, a to-be-hired product manager, and an AI consultant to deliver high-quality, timely product releases.
• Partner with marketing, research, and partnerships teams to translate user insights into scalable features.
• Create and maintain a roadmap that prioritizes user impact, data integrity, and platform sustainability.
• Champion responsible innovation, ensuring all product developments support the mission, maintain fiscal stewardship, and advance long-term sustainability.

AI, Analytics, and User Outcomes

• Lead AI experimentation, model integration, and deployment of agentic systems that adapt to user needs.
• Create and manage the AI development infrastructure and data pipelines for model training and deployment.
• Establish clear guardrails, evaluation frameworks, and transparency standards to ensure responsible AI behavior and alignment with SkillUp’s mission.
• Ensure data systems are designed to capture, interpret, and report meaningful worker outcomes.
• Provide guidance to SkillUp staff on the best use of AI tools and agents to support their work.

Leadership & Collaboration

• Build and mentor a remote, mission-driven product team that thrives at the intersection of technology, equity, and workforce innovation.
• Partner with SkillUp’s executive team to integrate product insights into organizational strategy, partnerships, and funding initiatives.
• Partner with fundraising and partnerships teams to align product innovation with funder priorities, translating philanthropic goals into scalable, user-centered product strategies.
• Drive collaboration with external partners, workforce systems, and funders to co-create solutions that respond to market needs and amplify collective impact.
• Represent SkillUp externally as a thought leader in ethical AI, career navigation, and workforce innovation.

Requirements

• 15+ years of experience in digital product management, ideally with exposure to workforce or social impact sectors.
• Proven track record of leading and managing distributed and cross-functional technical and engineering teams, with success in holding others accountable while investing a team in a vision.
• Knowledge and deep curiosity of AI and machine learning systems, particularly in building or deploying agentic AI or intelligent agents. Understanding of the technical components of AI to lead others to execute on SkillUp’s vision, including guardrails and feedback loops.
• Knowledge of machine learning algorithms, deep learning, and natural language processing.
• Strong understanding of user-centered design, data-informed decision-making, and impact measurement.
• Mission driven and committed to creating opportunity for low-wage workers.
• Fluent in a variety of technical languages and frameworks.

Salary & Benefits

• Salary:
  • Target salary for this position is $225,000 - $275,000 depending on experience and geography.
• Healthcare:
  • We currently pay 95% of your medical, dental, and vision coverage and 75% of the premium for your spouse and dependents. If you choose not to elect benefits you may receive an opt-out stipend of $2,000.
• Retirement:
  • We have a 401k Program with company matching. We match 100% of employee contributions up to the first 3% of pay.
  • Then 50% of employee contributions on the next 2% of pay.
• Paid Time Off: We value work-life balance and encourage our team members to take time off.
  • 4 weeks/20 Paid PTO days (25 PTO days after reaching the 3-year mark).
  • Two weeks of company shutdown during the week of July 4th and between Christmas and New Year’s.
  • All Federal Holidays.
  • 2 “Floater” days are to be used at your discretion.
  • Parental Leave: To help support new parents in the workplace, we offer 12 weeks of paid parental leave.
• Professional Development: We believe that developing our team members’ skills is a pathway to accomplishing our mission.
  • To this end, we offer you $1,000 annually for the professional development opportunities of your choice.
• Home Office: We will purchase a work computer for you.
  • We also provide a $75 monthly technology stipend ($900/annual for WiFi/cell).