Chris Tamasi

Director, Mid-Market Sales at Rippling

Brooklyn, New York, United States

About

As a Director of Sales at Rippling, I currently lead the Mid-Market East Region in a second-line role—managing a team of 7 sales Managers and 35+ Account Executives. My focus is on delivering results, fostering a collaborative team culture, and developing scalable processes through effective leadership and strategic execution. With over 10 years of experience in sales and leadership across organizations like LinkedIn, Lyra Health, and Rippling, I am dedicated to building & leading high-performing teams in fast growing businesses. In 2020, I published a children’s book, “Borders,” which explores the invisible lines that define our states, countries, and continents. “Borders” poses the question: “what if kids were in charge of making the map?” and gives space to young readers to shape our world in new and creative ways. There have been ~800+ copies sold and "Borders" is currently included in the recommended Massachusetts 5th Grade Curriculum. Outside of work, you will likely find me exploring the NYC food scene, spending quality time with friends & family, focusing on NYT Games, or strolling new neighborhoods in search of a delicious cup of coffee.

Experience

  • Rippling ()
    • Director, Mid-Market Sales
      Nov 2025 - Present · 9 mos

      Leading the Mid Market East Region--second-line role currently responsible for a sales team of 7 sales managers and 35+ AEs. Promoted 1 Manager to ENT Manager, 2 Managers to Sr. Manager, 2 AEs to Manager, 2 AEs to ENT AE, 4 AEs to Sr. AEs

    • Manager, Mid-Market Sales
      Dec 2023 - Nov 2025 · 2 yrs

      Led a sales team of 5-7 Mid-Market Account Executives, responsible for ~$5-6M annual quota. Helped hire ~15 AEs, 4 Managers, 1 Director - while developing strong team culture of collaboration, celebration, connectivity and high performance. FY'25 Highlights: - 132% Annual Quota Attainment (YTD), #2 in NAMER - President's Club Achievement - "Go and See" Work Magic Award Winner: company-wide, peer-nominated & executive team selected annual award, honoring those who most embody Rippling's leadership principles. - Promoted 2 AEs to Sr. AE FY'24 Highlights: - 101% Annual Quota Attainment - Manager MVP Award - Promoted 2 AEs to Sr. AE, 1 to ENT AE, 1 AE to MM TAM

  • Lyra Health (3 yrs 2 mos)
    • Manager, Mid-Market Sales (Partnerships Territory Director)
      Oct 2021 - Dec 2023 · 2 yrs 3 mos

      Led a sales team of 5 Partnerships Directors (AEs) who grew net-new business for Lyra Health within our Mid-Market segment. My team helped organizations with 1-3k employees offer Lyra's life-changing workforce mental health benefit to better support their employees, families, and company.

    • Enterprise, Account Executive (Partnerships Director)
      Nov 2020 - Dec 2021 · 1 yr 2 mos

      Grew net-new business for Lyra by partnering with leaders at large enterprise organizations to understand the measurable impact Lyra has on both their employees and business and facilitate launching Lyra as a life-changing benefit for their employees and families.

  • LinkedIn (5 yrs 4 mos)
    • Mid-Market Account Executive - Learning Solutions
      Jan 2019 - Oct 2020 · 1 yr 10 mos

      Partnered with mid-market sized enterprise businesses on effectively leveraging LinkedIn Learning to strengthen employee engagement, close skills gaps, and build a talent pipeline to set business up for success for the long-term in our new world of work.

    • SMB Account Executive - Learning Solutions
      May 2017 - Dec 2018 · 1 yr 8 mos

      Partnered with small-to-medium sized enterprise businesses to address employee engagement and retention challenges by leveraging LinkedIn Learning to positively impact culture and the bottom line.

    • Senior Sales Development Representative - Sales Solutions
      Mar 2016 - Apr 2017 · 1 yr 2 mos

      Helped transform the sales profession through Social Selling and Sales Navigator as LinkedIn scaled it's newest business at the time. Partnered with Mid-Market and then promoted to support Enterprise Account Executives to source new business opportunities.

  • Summer Intern at Game On Nation
    Jun 2013 - Aug 2013 · 3 mos

    Game On Nation is one of the most respected firms in communication, leadership, resiliency, and teambuilding training. Game on is nationally recognized for working with some of the most demanding and high-profile corporations, leagues, and teams, creating unparalleled commitment and buy-in, with results that last. I collaborated directly with company's President, Vice-President, and Logistics Manager to review sales pipeline, coordinate logistics, and execute plans for upcoming events/presentations. I had the opportunity to observe several training sessions, and even assisted with writing improvisation-based curriculum.