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Ryley Reynolds

Investor Investor

Boston, Massachusetts

Overview 

Ryley Reynolds is a VC Investor based in New York, New York, with a background in Venture Capital and Leadership. With experience at Insight Partners, Benchmark, and Thrive Capital, Ryley has excelled in strategic partnerships and brand management, with a strong focus on investing in sectors like Social Commerce and Enterprise. Ryley holds a Master of Business Administration from Harvard Business School and has held key roles such as President at Harvard Student Agencies and Managing Director at The Harvard Shop, showcasing a track record of leadership and success in both academic and professional settings.

Work Experience 

  • Startup Advisor & Angel Investor | Fundraises & Exits

    2023 - Current

    I work closely with founders at the Series A stage and beyond, guiding them through the complexities of fundraising and exits with a focus on storytelling. As a coach and collaborator, I help uncover insights from their metrics, refine their messaging and materials, and craft compelling narratives that resonate with investors and stakeholders. My goal is to empower founders to succeed during these pivotal milestones, building confidence in their vision and strategy. I also collaborate with emerging venture and growth equity funds to shape fundraising strategies and develop narratives that connect meaningfully with limited partners.

  • Principal

    2021 - 2023

Insight Partners is a global software investor that partners with high-growth technology, software, and Internet startup companies.

  • Investment Team

    2020 - 2020

Benchmark focuses on early-stage venture investing in mobile, marketplaces, social, infrastructure, and enterprise software.

  • Investor

    2017 - 2020

Thrive Capital is an investment firm that builds and invests in internet, software, and technology-enabled companies.

Raised $120,000,000.00 from Petershill Partners.

  • Investment Associate

    2015 - 2017

Insight Partners is a global software investor that partners with high-growth technology, software, and Internet startup companies.

  • Computer Science Teaching Fellow

    2015 - 2015

    Assisted the School of Engineering and Applied Sciences course Computer Science 179: Design of Useful and Usable Interactive Systems, which focuses on user interfaces and user experience (UI/UX), need-finding, and web-based mobile application development. Instructed a weekly studio course and coordinated logistics and grading for the class of over 60 students.

  • President

    2014 - 2015

    Managed the world's largest student-run corporation generating more than $4 million in revenues annually with 12 unique businesses and over 500 employees including 35 student managers.

  • Managing Director at The Harvard Shop

    2013 - 2014

  • Custom Orders Manager at The Harvard Shop

    2011 - 2013

Harvard Student Agencies is a student-run company.

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