Ryan Kaiser

Sales Executive

San Francisco, California, United States24 yrs 1 mo experience

Highly Stable

Key Highlights

Led sales teams to achieve significant revenue growth.
Expert in developing go-to-market strategies for SaaS products.
Proven track record in managing cross-functional teams.

Stackforce AI infers this person is a SaaS and Fintech sales leader with extensive experience in business development and customer success.

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Skills

Core Skills

Sales LeadershipGo-to-market StrategyHr Strategy/technologyCustomer SuccessBusiness DevelopmentSales ManagementCustomer ExperienceSales StrategyTalent AcquisitionSales DevelopmentStrategic PlanningSales OperationsEcommerce StrategyBusiness StrategyCompetitive AnalysisCorporate StrategyStrategy DevelopmentCustomer Insights

Other Skills

Account ExecutivesBusiness OperationsConsultingCross-functional Team LeadershipDelivering operating resultsE-commerceEcommerceEnterprise SoftwareHR technologyInternational SalesInternetLeadershipLogisticsManagementManagement Consulting

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

Rippling

SVP of Sales

Sep 2022 – Present · 3 yrs 6 mos · San Francisco, California, United States

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.

sales leadershipgeneral managemententerprise & SMB salesrevenue operationscustomer successgo-to-market strategy+3

Housecanary

Chief Revenue Officer

Dec 2019 – Sep 2022 · 2 yrs 9 mos · San Francisco Bay Area

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.

go-to-market strategysalesbusiness developmentcustomer successpartnershipscustomer/revenue operations

3 roles

Head of North America Sales | LinkedIn Learning & Lynda.com

Promoted

Jan 2016 – Dec 2019 · 3 yrs 11 mos · San Francisco Bay Area

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.

sales managementbusiness developmentcustomer experience

Regional Sales Leader | LinkedIn Talent Solutions

Jan 2015 – Dec 2015 · 11 mos · San Francisco Bay Area

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.

sales strategytalent acquisitioncustomer engagement

Head of Americas Sales Development & Global Sales Operations

Jun 2013 – Dec 2014 · 1 yr 6 mos · San Francisco Bay Area

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.

sales developmentstrategic planningdemand generation

Ebay

2 roles

GM/Director | Cross Border eCommerce at eBay

Promoted

Mar 2011 – Jun 2013 · 2 yrs 3 mos · San Francisco Bay Area

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.

eCommerce strategycustomer experiencebusiness development

eBay/Marketplaces Corporate Strategy Group

Apr 2010 – Mar 2011 · 11 mos · San Francisco Bay Area

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.

business strategycompetitive analysismarket strategy

Monitor deloitte (ex monitor group)

2 roles

Senior Engagement Manager

Promoted

Jan 2007 – Apr 2010 · 3 yrs 3 mos · San Francisco Bay Area

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.

corporate strategybusiness developmentclient engagement

Associate & Analyst

Jan 2000 – Jan 2005 · 5 yrs

Partnered with client teams to develop strategy recommendations. Deep experience driving business decisions & customer insights through customer research, statistical analysis and financial modeling.

strategy developmentcustomer insightsstatistical analysis