Ryan Kaiser

SVP of Sales at Rippling

San Francisco, California, United States

About

I am passionate about building great teams, scaling great businesses, simplifying complex problems and helping our customers achieve success. Senior revenue / sales leader at Rippling. My customer-focused team partners with businesses to help them to simplify, automate and manage all of their HR, IT and Finance/Spend in one unified workforce platform. Rippling is the workforce management platform that unifies HR, IT, finance, and more. Built on a single source of truth for employee data and integrated with 700+ apps, Rippling allows businesses to execute more efficiently. By connecting every workforce system to a single source of truth for employee data, businesses can automate all of the manual work they normally need to do to make employee changes. Specialties: sales leadership, general management, enterprise & SMB sales, revenue operations, customer success, go-to-market strategy, demand gen, talent development, HR strategy/technology.

Experience

  • SVP of Sales at Rippling
    Sep 2022 - Present · 3 yrs 11 mos

    Senior revenue / sales leader at Rippling. Through an incredible senior leadership team, my customer-focused team partners with businesses to help them to simplify, automate and manage all of their HR, IT and Finance/Spend — payroll, benefits, HCM platform, LMS, ATS, performance management, expenses, devices, apps, integrations & more — in one unified workforce platform. Rippling is the workforce management platform that unifies HR, IT, finance, and more. Built on a single source of truth for employee data and integrated with 700+ apps, Rippling allows businesses to execute more efficiently. Rippling provides one unified platform offering our customers HCM Suite, Talent Suite, Payroll Suite, IT Suite and Finance Suite. By connecting every workforce system to a single source of truth for employee data, businesses can automate all of the manual work they normally need to do to make employee changes. Based in San Francisco with offices across north America, EMEA, APAC. Rippling was valued at $16.8B in the May 2025 Series G Round, including investments from the world’s top investors — including Goldman, GIC, Sands Capital, Kleiner Perkins, Founders Fund, Sequoia, and Bedrock — and was named one of America's best startup employers by Forbes (#12 out of 500) and the fastest-growing private company in the Bay Area by the San Francisco Business Times.

  • Chief Revenue Officer at HouseCanary
    Dec 2019 - Sep 2022 · 2 yrs 10 mos

    Chief Revenue Officer responsible for HouseCanary's go-to-market strategy and execution. My team included sales, business development, customer success, partnerships and customer/revenue operations. HouseCanary developed data-driven software solution for real estate and financial services companies. Built industry-leading Digital Solutions driven by data science for residential real estate to fuel the customer-focused platforms. HouseCanary provides data/analytics solutions through the HouseCanary Solutions Platform and ComeHome Platform. Focus on customers in residential real estate and financial services, including banks, IMBs, capital markets, real estate investors/operators and real estate tech players.

  • LinkedIn ()
    • Head of North America Sales | LinkedIn Learning & Lynda.com
      Jan 2016 - Dec 2019 · 4 yrs

      LinkedIn's Learning Solutions business provides an online learning platform that helps anyone learn business, leadership, software, technology and creative skills to achieve personal and professional goals. LinkedIn Learning partners with corporations & organizations globally to help their employees build critical skills and develop their careers. Through a talented group of regional sales managers and senior leaders, I led North America Sales & new business for Lynda.com/LinkedIn Learning Solutions.

    • Regional Sales Leader | LinkedIn Talent Solutions
      Jan 2015 - Dec 2015 · 1 yr

      Partnered with our customers to transform the way that organizations find, hire and retain great talent. Within LinkedIn Talent Solutions, I led a sales team that worked with our customers to develop solutions to help them achieve their talent strategy & goals.

    • Head of Americas Sales Development & Global Sales Operations
      Jun 2013 - Dec 2014 · 1 yr 7 mos

      LinkedIn's Global Sales Development organization is the new business development engine and talent pipeline for LinkedIn’s global sales teams for our corporate businesses: Talent Solutions, Sales Solutions, Marketing Solutions. The leadership coaches and develops professionals to realize their potential. Sourced over $150M in new bookings in 2014. Within Sales Development, I led as: - Global Head of Inbound Sales Development: Led through a talented team of leaders/managers for Global inbound with teams in Americas, EMEA, Asia Pacific. - Head of North America/Latin America Sales Development: Managed a talented team of sales development leaders/managers for LinkedIn's largest business: Talent Solutions. - Global Head of Sales Operations: Operated as "COO" for Sales Dev across LinkedIn. Managed a talented team of sales operations managers to drive strategic programs, forecasting, incentive design, strategic planning and Global Inbound Demand Gen.

  • eBay ()
    • GM/Director | Cross Border eCommerce at eBay
      Mar 2011 - Jun 2013 · 2 yrs 4 mos

      General Manager of $2B retail sales ecommerce business at eBay. Led team responsible for international sales, operations, customer experience, product marketing, business development/partnerships, global logistics solutions. Managed strategy to execution. Focused on B2B & B2C customers in US, China/Asia Pacific and Europe across all retail categories. eBay accounted for over $68B in global core retail sales in 2012.

    • eBay/Marketplaces Corporate Strategy Group
      Apr 2010 - Mar 2011 · 1 yr

      Led team in the eBay/Marketplaces Corporate Strategy Group to: Develop business strategy; Conduct annual strategic planning; Drive competitive & market analysis/strategy; and Develop Investor & Board of Directors strategy communication.

  • Senior Engagement Manager at Monitor Deloitte (ex Monitor Group)
    2007 - Apr 2010 · 3 yrs 4 mos

    Monitor Group was a global strategy consulting firm with 1,200+ professionals in 26+ offices internationally. Monitor was acquired by Deloitte Consulting in 2013 and is now Monitor Deloitte. Senior Engagement Manager within a global management consulting firm. Advised executives focused on corporate strategy, marketing & sales strategy, learning & development and operations. Led engagement teams & partnered with client teams to deliver corporate and business unit strategies for growth and operational efficiency. Conducted sales / business development for new client engagements. Industry focus in healthcare, biopharma, technology, consumer products.