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Megan O'connor

VP Partnerships at Chegg

New York, New York

Overview 

Megan O'Connor is the Vice President of Partnerships at Chegg, where she has excelled in leading business-to-institution go-to-market strategies and strategic partnerships. She has a strong background in education and the future of work, with notable achievements in founding, operating, and investing in various ventures in these sectors. Highlights of Megan's career include her roles as the Co-founder and CEO of Hi Clark (acquired by Noodle) and her current position as VP Partnerships at Chegg, where she has demonstrated expertise in entrepreneurship, strategic planning, and social entrepreneurship.

Work Experience 

  • Vice President, Head of Business-to-Institution GTM

    2024 - Current

    Leading the University Partnership Team for Chegg's student-first learning platform

  • Vice President, Head of Strategic Partnerships @ Chegg Skills

    2021 - 2024

    Manage revenue for Chegg Skills across strategic partnerships, channel partners, and enterprise sales.

  • Contributor

    2022

  • Impact Advisory Committee

    2021

Apollo is an asset management firm that focuses on the private investment-grade and fixed-income markets.

Raised $5,587,507,641.00 from BNP Paribas, Barclays and Sumitomo Mitsui Trust Bank.

  • Venture Partner

    2021 - 2023

    Gutter Capital invests in early-stage, mission-driven businesses. We partner closely with founders to build companies of consequence impacting affordability, economic mobility, or sustainability for the average American.

We invest in ideas and individuals to advance the American experiment through affordability, economic mobility, and sustainability.

  • Advisor

    2021 - 2022

    Acquired by Power School in 2022. Kinvolved catalyzes students, parents, educators, and community stakeholders around a common mission: to improve family engagement and attendance in service of elevating student outcomes.

Kinvolved is a developer of a social enterprise platform designed to improve student attendance and reduce chronic absenteeism.

Raised $4,100,000.00 from Fund for Health, New York Ventures, New York Ventures, u2i, GingerBread Capital, Twilio.org, Excell Technology Ventures, The Draper Richards Kaplan Foundation, New York Ventures and The Draper Richards Kaplan Foundation.

  • Entrepreneur In Residence

    2020 - 2021

    - Serve on the Senior Leadership team advising on product and growth strategy - Launched Kaplans first Career Exposure product "Boost by Kaplan" in partnership with Google and Myers Briggs

Bauder College is a school in Atlanta.

  • Fellow (ODA1)

    2020 - 2020

    On Deck Angel Investors Cohort #1

On Deck is a community platform designed to develop different ideas and build companies.

Raised $20,000,000.00 from Pioneer Fund.

  • Advisor

    2016 - 2020

  • Chief Growth Officer

    2015 - 2016

    - Executed fundraising and growth strategies for the Human Ventures parent company - Supported the fund's portfolio companies

Human Ventures is an investment fund based in New York that provides support to founders in the early stages of their businesses.

  • Co-founder and CEO

    2016 - 2019

    Clark, NYC — Co-Founder & CEO (Acquired) - Developed SMB platform for tutors processing $4mm monthly - Raised $4.5mm in series seed led by Lightspeed Venture Partners - Hired and managed a team of 17 from PolicyGenius, Kickstarter, and others - Lead the Leadership team of Product Designer, CTO, and Head of Product - Created mobile app featured in Apple app store and Apple’s show Planet of the Apps

Clark is software for your tutoring business.

Raised $3,500,000.00 from Lightspeed Venture Partners, Winklevoss Capital, Rethink Education and Flat World Partners.

  • Director of Development

    2013 - 2015

    Pencils of Promise (PoP), NYC Director of Development - Served as the EdTech nonprofit organization’s top-performing fundraiser - Key relationship manager for PoP’s HNW investors, corporate partners, and influencers, including PoP’s invitation-only giving circle, the Advisory Board.

Pencils of Promise create schools, programs and global communities around the education for all.

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