Jeff R.

New York, NY, USA

Product and Tech Leader | Ethical AI | EdTech | Scaling Platforms and Teams | NYC

Highly technical and commercially focused product leader with 15+ years driving strategy and delivering outcomes in EdTech, B2B SaaS and HR Tech. Shipped GenAI features to real users with measurable business impact and disciplined economics. Hands-on product architect and builder who thrives solving user needs with empathy, pragmatism and deep technical understanding in collaboration with Engineering, Design and GTM.

Jeff R.

Experience

  • SkillCycle

    SkillCycle

    CO-Founder and COO/CPO

    Feb 2023 - Jul 2025

    SkillCycle is a Human Capital Development company, offering HR solutions focused on employee learning and performance management.

    • Scaled SkillCycle 500% over 4 years by building a robust product team and introducing innovative HR solutions.
    • Created the first unified talent platform integrating performance and development workflows.
    • Architected Aida, an AI-powered assistant providing personalized feedback and development plans.
    • Led data analytics effort, integrating data to build a cohesive KPI/OKR system.
  • SkillCycle

    SkillCycle

    Co-Founder and Chief Product Officer

    Jul 2021 - Feb 2023

  • Success Academy Charter Schools

    Success Academy Charter Schools

    Head, Schooling Services

    Nov 2019 - Jun 2021

    Success Academy Charter Schools is a network of public charter schools in NYC focused on providing transformative K-12 education.

    • Enhanced decision-making by leading data analytics for educational institutions.
    • Developed data warehouses and dashboards improving data access and visualization.
    • Managed a successful transition to remote schooling during the pandemic.
  • McGraw-Hill Education

    McGraw-Hill Education

    Vice President, Technical Product Management

    Nov 2017 - Nov 2019

    McGraw Hill provides educational resources and platforms for instructors and students worldwide.

    • Achieved 25% market share growth for McGraw-Hill Connect by integrating AI features.
    • Forged strategic partnerships positioning the platform as an innovation leader.
  • Taskstream-Tk20

    Taskstream-Tk20

    Vice President of Product Management

    Jun 2014 - Sep 2017

    Watermark offers software solutions supporting higher education institutions in assessment and accreditation management.

    • Transformed product development culture, improving user experiences and launching new products.
    • Led a successful initiative with Gates Foundation, fostering widespread adoption and expansion of Aqua.
    • Integrated teams post-merger and developed a new product strategy and roadmap.
  • Pearson plc

    Pearson plc

    VP of Product, School Systems

    Jan 2014 - Jun 2014

    Pearson is a global education company providing textbooks, digital learning solutions, and assessments.

    • Organized a new product marketing function, implementing a strategy for consolidation of key products.
    • Managed product responsibility for K-12 SIS and LMS, enhancing overall product offerings.
  • Pearson plc

    Pearson plc

    VP Product Management, K-12 Technology

    May 2012 - Dec 2013

    • I led product management for Schoolnet, Pearson's award-winning instructional improvement system. Schoolnet provides the only unified solution to align student assessment, curriculum and instruction; guide collaborative, data-informed discussion; and enable targeted instruction for every student.
    • The job required me to grow and mentor a product and UX team during a time of both tremendous internal change and external pressure to deliver against high-profile contractual engagements. During my time we:
    • Planned and led five consecutive on-time releases of market-leading student assessment and teacher evaluation capabilities to a user base that doubled to over 8 million students.
    • Served as a critical partner and thought leader to senior leadership at several states and large urban school districts using the Schoolnet product to support ambitious new assessment, curriculum and teacher evaluation initiatives.
    • Doubled the number of agile product teams across three locations in six months to increase velocity and meet commitments.
    • Turned around a stalled "one Pearson" product integration project and delivered a new Cloud-based data hub for class-roster sharing and single sign-on across disparate learning applications to a base of 25 pilot customers (500K students).
    • Developed and implemented strategies for integrating products from different Pearson divisions; Escambia County (FL) School District won a Gold award from the IMS Global Learning Consortium for the improvements to learning they made with our solution.
  • Pearson plc

    Pearson plc

    VP, Product Management LTG Core Technologies

    Feb 2008 - May 2012

    • Directed product management for core technologies supporting top learning applications, generating $600M in digital revenue.
    • Managed cross-functional solutions spanning analytics, identity management, and e-commerce.
  • BiddingForGood

    BiddingForGood

    Director, Analytics

    Jan 2006 - Feb 2008

    BiddingForGood is an online fundraising auction platform connecting nonprofits with philanthropic shoppers.

    • Directed internal business intelligence efforts and customer-facing analytics features.
    • Designed an internal data warehouse for strategic guidance and operational support.
    • Integrated Salesforce.com to provide actionable data for at-risk accounts.
  • Pearson Education

    Pearson Education

    Director, Technical Project Management

    Apr 2004 - Dec 2005

    • Managed engineering resource allocation and project management for core technology platforms.
    • Provided analysis and forecasts for product usage, supporting decision making and sales strategies.
  • Pearson Education

    Pearson Education

    Engineering Program Manager

    Feb 2001 - Apr 2004

    • Managed development of Pearson's Subscription Management System, ensuring system-wide integration in education apps.
    • Supervised a cross-functional team to deliver a successful subscription management platform.
  • Voter.com

    Manager of Account Services

    Sep 1999 - Feb 2001

    Voter.com was an independent political information website.

    • Designed and implemented a content management system for campaign websites.
    • Managed advertising and content traffic supporting over 1,000 campaigns and advocacy groups.
  • Cahners Business Information

    Customer Support Representative

    Apr 1997 - Sep 1999

    Cahners Business Information was involved in new media projects for manufacturing publications.

    • Developed online help resources and managed high volumes of user and customer support emails.
    • Provided management with analytical reports of user feedback and trends to strengthen operations.

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