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Henry Toole

Principal at Left Lane Capital

New York City Metropolitan Area

Overview 

Henry Toole is a Principal at Left Lane Capital in New York City, specializing in investments at Series A and Series B stages in sectors such as Digital Health and FinTech. With a background at Microsoft and Casper, he has successfully invested in companies like AnswersNow at the Series A stage, showcasing his expertise in strategic investment decisions.

Work Experience 

  • Principal

    2021 - Current

  • Vice President

    2019 - 2021

    Left Lane Capital is a venture capital and early growth equity firm focused on high-growth, high-retention consumer and internet technology businesses at Series A - C across North America, Europe and Israel.

Left Lane Capital is a venture capital and seed-growth equity firm that invests in high-growth internet and consumer technology businesses.

  • Associate

    2017 - 2019

  • Data Analyst

    2016 - 2017

    Responsible for retention marketing and onsite analytics at Casper.

Casper is a sleep startup that launches a comfortable mattress sold directly to consumers, eliminating commission-driven inflated prices.

Raised $339,700,000.00 from Gordon Whyte, New Enterprise Associates, IVP, Target, Sand Hill Angels, Parkway Venture Capital, Dani Reiss, Norwest Venture Partners and Alumni Ventures.

  • Surface Commercial Channel Manager

    2016 - 2016

    Managed commercial channel strategy for all Surface products through distributors and Microsoft Stores

  • Band and Health Product Marketing Manager

    2015 - 2016

    Established the commercial channel for the Microsoft Band and managed from end to end

  • Windows Business Planner

    2014 - 2015

    Strategic planning for Microsoft Consumer portfolio of devices

Microsoft Advertising provides digital advertising solutions.

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