Adanna U.

Experience

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  Mainstay

  Vice President, GTM

  Jan 2025 - Present

  Guide learners to success with conversations designed to spark action. Our human centered, AI enhanced approach helps students access and achieve higher learning by turning barriers into milestones along their journey.

  • Own go-to-market strategy and strategic partnerships for Mainstay’s student success platform, aligning product, research, and sales to drive institutional adoption.
  • Built partnership plays and pilot models that translate Mainstay’s evidence base (including 12 randomized controlled trials) into measurable enrollment and retention outcomes for higher-ed customers.
  • Designed and launched enterprise and system-level collaborations to scale personalized, AI-enabled student outreach while preserving human escalation pathways.
  • Partner with product, research, and implementation teams to translate trial insights into repeatable GTM assets (playbooks, ROI cases, pilot scaffolds).
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  Mainstay

  Vice President, Partnerships

  Jan 2025 - Present

  • Led new-product GTM and partnership strategy to expand Mainstay’s footprint across higher‑ed and student‑support organizations.
  • Built partner engagement frameworks and commercial pilots that translate Mainstay’s conversational AI into demonstrated persistence and belonging outcomes.
  • Coordinated cross-functional launch playbooks (sales, implementation, research) to accelerate partner onboarding and scale adoption across campuses.
  • Worked with research and product teams to ensure messaging, escalation, and privacy guardrails aligned with institutional policy and student needs.
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  Agence

  Career Mobility Coach

  Feb 2022 - Present

  Career coaching for job advancement and transitions. Clients land promotions or offers at top companies and high-growth startups through positioning strategy, interview prep, and negotiation support. Founded by Adanna Ukah, EdTech VP, Co-Active and MLT-trained coach, and former recruiter.

  • Provide 1:1 career mobility coaching focused on positioning, interview preparation, and offer negotiation for mid‑to‑senior professionals.
  • Advise career centers and individual clients on transition strategy—resume and LinkedIn positioning, storytelling, and competency framing for roles at top tech, consulting, and startup employers.
  • Deliver negotiation coaching that improves offer outcomes and helps clients secure higher base, equity, and total-comp packages.
  • Design modular coaching curricula and resources that career centers can adopt for cohort-based or individualized client support.
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  Chegg Inc.

  Senior Director, GTM

  Aug 2022 - Nov 2024

  A Smarter Way to Student!

  • Led GTM and business development for Chegg Skills’ B2B/enterprise category—building employer and channel partnerships for adult professional training.
  • Served as an internal subject-matter expert and lead seller, shaping Chegg’s strategic pivot from consumer/student study help to adult upskilling and professional education.
  • Defined enterprise value propositions, pricing constructs, and pilot-to-scale plays for learning-at-work customers and channel partners.
  • Coordinated cross-functional launches with product, marketing, and partnerships to accelerate enterprise bookings and product-market fit in adult learning.
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  Chegg Inc.

  Senior Director, Business Development

  Aug 2022 - Nov 2024

  • Directed business development and GTM for Chegg Skills’ enterprise channel—shaping market strategy for adult learning products.
  • Owned strategic partnerships with employers and enterprise buyers to place Chegg Skills into corporate learning and upskilling programs.
  • Defined commercial pilots, success metrics, and case studies to accelerate enterprise sales and prove ROI for employer customers.
  • Coordinated with product and marketing to tailor offerings for employer hiring and reskilling use cases.
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  Google

  Product Marketing Lead, Grow with Google

  Nov 2021 - Aug 2022

  A problem isn't truly solved until it's solved for all. Googlers build products that help create opportunities for everyone, whether down the street or across the globe. Bring your insight, imagination and a healthy disregard for the impossible. Bring everything that makes you unique. Together, we can build for everyone.Check out our career opportunities at goo.gle/3DLEokh

  • Owned product marketing and partner enablement for Grow with Google / Google Career Certificates—positioning 6–9 month, job‑ready trainings to learners and employers.
  • Built go-to-market messaging, partner collateral, and launch campaigns that increased employer awareness and downstream hire pipelines for certificate graduates.
  • Worked with employer and learning partners to embed certificates into hiring pathways and upskilling programs, demonstrating outcomes and readiness.
  • Coordinated measurement frameworks to track certificate-to-hire conversion and employer adoption signals for continuous improvement.
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  Google

  Partnerships Lead, Grow with Google

  Nov 2021 - Aug 2022

  • Built partnerships for Grow with Google / Google Career Certificates to expand employer pathways and learner placement.
  • Negotiated collaborations with employers, workforce partners, and training providers to create hiring pipelines for certificate completers.
  • Developed joint go-to-market initiatives and measurement plans to demonstrate certificate efficacy and employer trust.
  • Advised internal teams on partner segmentation and enablement to scale adoption across industries and regions.
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  Guild

  Director, Learning Partnerships

  Aug 2020 - Oct 2021

  We're on a mission to unlock opportunity for America's workforce through education and upskilling

  • Led business development for learning partners and programs across degrees, allied health, skilled trades, and short-form certificates to serve frontline employees at F1000 employers.
  • Owned partner sourcing, commercial negotiation, and program design to align institutional offerings with employer workforce needs and tuition-benefit models.
  • Built enablement materials and intake processes to accelerate onboarding, reduce partner CAC, and create predictable enrollment pipelines for institutional partners.
  • Coordinated cross-functional pilots with employer stakeholders to demonstrate ROI (hiring, retention, upskilling) and inform scale decisions.
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  Guild

  Senior Manager, Learning Partnerships

  May 2020 - Aug 2020

  • Owned GTM strategy, portfolio planning, and pipeline development for Guild’s Learning Marketplace.
  • Cultivated and qualified institutional and program partners to expand employer-facing catalog for tuition-covered upskilling.
  • Designed prioritization frameworks and go/no-go criteria for pilots to optimize commercial outcomes and partner success.
  • Collaborated with sales and implementation teams to convert pilots into recurring programs and improve partner satisfaction and retention.
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  Guild

  Engagement Manager, Entangled Group (now Guild)

  Nov 2019 - Jun 2020

  • Led case teams in K‑12 innovation consulting, serving nonprofit, charter school, college access, and philanthropic clients.
  • Owned project delivery end-to-end: needs assessment, program design, stakeholder engagement, and implementation planning.
  • Developed research-backed recommendations and operational plans to improve student access and program sustainability.
  • Supported integration activities and knowledge transfer after Entangled Group’s acquisition by Guild (May 2020).

• Entangled Group (now Guild Education)

  Engagement Manager

  Nov 2019 - Jun 2020

  Entangled Group (now Guild Education) is a company.

  • Served as engagement manager and case team leader for K‑12 innovation projects, advising nonprofits, charters, and philanthropic clients.
  • Owned project scoping, research synthesis, program design, and client-facing deliverables to drive measurable program improvement.
  • Coordinated multi-stakeholder engagement and implementation planning to ensure sustainable adoption of recommendations.
  • Supported transition and integration activities following Entangled Group’s acquisition by Guild.
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  Bain & Company

  Consultant

  Jul 2017 - Aug 2019

  We're a global consultancy that helps the world’s most ambitious change makers define the future.

  • Delivered strategy and commercial due diligence across sectors (mining M&A, supermarket growth strategy, private equity diligence).
  • Built financial and market models to evaluate transaction economics, value-creation levers, and integration risk.
  • Led client workshops and synthesized recommendations into actionable roadmaps for growth, M&A integration, or portfolio optimization.
  • Managed junior team members on analysis, client presentations, and implementation support.
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  Bain & Company

  Case Team Leader / Consultant

  Jul 2017 - Aug 2019

  • Led case teams at Bain to deliver commercial due diligence, M&A support, and growth strategy across mining, retail (supermarkets), and private equity portfolios.
  • Owned structuring of analyses, financial modeling, and synthesis of strategic recommendations for senior clients and investment committees.
  • Managed cross-functional project teams and ensured high-quality client deliverables under tight timelines.
  • Translated insights into pragmatic value-creation plans and post-deal integration guidance.
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  EY-Parthenon

  Summer Consultant - Education Practice

  Jun 2016 - Aug 2016

  EY provides consulting, assurance, tax and transaction services that help solve our client's toughest challenges and build a better working world for all.

  • Supported the Education practice at EY‑Parthenon on a Universal Pre‑K strategy and program development engagement for the City of Boston.
  • Conducted stakeholder analysis, service-design research, and financial/operational modeling to inform program options.
  • Authored implementation roadmaps and metrics to guide phased launch and measure early program performance.
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  Education Pioneers

  Manager, Fellowship Recruitment

  Nov 2013 - Jul 2015

  Education Pioneers recruits, connects, and advances professionals from diverse backgrounds to solve problems from outside of the classroom so students and teachers succeed inside of the classroom.

  • Managed national recruitment for Education Pioneers fellowships—designing candidate engagement and outreach strategies to diversify the applicant pool.
  • Led recruitment and selection efforts that resulted in the organization’s largest and most racially diverse fellowship class.
  • Optimized outreach channels, screening processes, and communications to improve candidate experience and conversion.
  • Partnered with internal stakeholders to align fellowship competencies to placement partner needs and improve match quality.
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  ConnectEDU

  Senior Associate

  Jul 2013 - Oct 2013

  ConnectEDU is a technology company, founded and grounded in education, committed to informing students of the broadest range of choices as they transition from school to college to career. Our technology solutions help students find and prepare for college and career opportunities, achieve a secure financial future, and ultimately expand their economic prospects.

  • Supported business development and partner engagement to expand ConnectEDU’s reach among college- and career-access organizations.
  • Contributed to partner onboarding, requirements gathering, and program configuration to ensure product fit for local contexts.
  • Helped develop outreach materials and reporting dashboards to demonstrate impact and inform partner decision-making.
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  ConnectEDU

  Associate

  Jul 2011 - Jun 2013

  • Owned business development and product marketing for district and state partners in Louisiana, Michigan, and Massachusetts.
  • Served as client lead for ConnectEDU’s first mobile app and scholarship-tracker product—coordinating product requirements, pilot launches, and user outreach.
  • Executed go‑to‑market communications and training for school and district staff, increasing platform adoption among families and counselors.
  • Collected user feedback and usage analytics to prioritize product enhancements and improve retention.
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  Yale University

  Recruitment Coordinator / Tour Guide

  Sep 2008 - Jun 2011

  Since its founding in 1701, Yale University has been dedicated to expanding and sharing knowledge, inspiring innovation, and preserving cultural and scientific information for future generations.

  • Acted as recruitment coordinator and campus tour guide—representing Yale to prospective students and families with high energy and professionalism.
  • Organized and led campus visits, information sessions, and admissions events to improve prospective student engagement and yield.
  • Collaborated with admissions staff to collect prospective student feedback and refine tour content and logistics.