Rob Chaplinsky
InvestorCo-Founder & Managing Director at Link Ventures · Managing Director at Bridgescale Partners
Incline Village, Nevada, United States
Writes $1M – $8M checks
Find your path to Rob
374 people in our graph share verified history with Rob — schools, employers, funds. One of them is your warm intro.
John KimunlockedRob: together at Harvard Business School (1992–1994)
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Rob: together at Intel
×6Rob: together at Harvard Business School
Rob: together at Xactly
About
Rob Chaplinsky, Canadian-born Silicon Valley–based managing director, bridges Canadian and U.S. tech, serves on fintech boards including MotoRefi and Caribou, and uses large internet data to spot AI consumer opportunities.
Invests in
AI & Machine LearningConsumerFintechInsurTechMarketplaces
Experience
- Link VenturesManaging Directorcurrent2018 — presentGreater Boston Area
- MultipleBoard Director, Chairman & Audit Committee Member — Multiple Companiescurrent1996 — present
- Bridgescale PartnersManaging Directorcurrent2005 — presentMenlo Park, CA
- CaribouBoard Member, Investor2020 — 2025Arlington, VA
- Trust & WillBoard Member, Investor2020 — 2023San Diego County, CA
- LoopSeed Investor2017 — 2021
- Xactly CorpInvestor, Advisor2010 — 2017San Jose, CA
- AxonifyInvestor | Advisor | Startup Coach | Mentor | Board member | Chairman2012 — 2016Waterloo, Canada Area
- BlueCatInvestor | startup coach | advisor | mentor | stategic advisor | Board Member2009 — 2016Toronto, Canada Area
- BiolinqAdvisor2014 — 2016Greater San Diego Area
- DryftCEO, co-founder2012 — 2014menlo park
- Vision CriticalInvestor, Advisor2010 — 2014Vancouver, Canada Area
- CeridianInvestor, Board Member2010 — 2012Toronto, Canada Area
- ProofpointInvestor, Board Observer2006 — 2012Sunnyvale, CA
- RyppleInvestor, Board Member2010 — 2011Toronto, Canada Area
- Mohr Davidow VenturesGeneral Partner1998 — 2005Menlo Park, CA
- Hambrecht & QuistSeñior Research Analyst, Investment Banking1996 — 1998San Francisco, CA
- IntelMobile Product Manager1990 — 1996Santa Clara, CA
Skills & more
Mentoring1Leadership4Management7Strategy6SaaS22Enterprise Software1Software as a Service (SaaS)3semiconductorsBoard of DirectorsVenture Capital78Corporate Venture CapitalBusiness Strategy26
+12 more
Go-to-Market StrategyArtificial Intelligence (AI)executive recruitingFundraisingMergers & Acquisitions (M&A)Corporate GovernanceInitial Public Offerings (IPO)Audit CommitteeMobile MarketingMobile ApplicationsMobile TechnologyEntrepreneurshipLanguages Russian
From Rob's professional profile.
Colleagues at Link Ventures
Alexander D. Wissner-Gross
Investor at Link Ventures
Alexander Wissner-Gross
Managing Director at Reified
Bill McCarran
COO at Vestigo Ventures
Boaz Fachler
Managing Director at Link Ventures
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Cindy Blanco
Chief Financial Officer at Link Ventures
Cynthia Blanco
CFO at Link Ventures
Dan Oliveri
Chief of Staff at Link Ventures
Dave Blundin
Managing Partner at Link Ventures
Frequently asked questions
- Who is Rob Chaplinsky?
- Rob Chaplinsky, Canadian-born Silicon Valley–based managing director, bridges Canadian and U.S. tech, serves on fintech boards including MotoRefi and Caribou, and uses large internet data to spot AI consumer opportunities.
- Where does Rob Chaplinsky work?
- Rob Chaplinsky is Co-Founder & Managing Director at Link Ventures.
- What does Rob Chaplinsky invest in?
- Rob Chaplinsky invests in AI & Machine Learning, Consumer, Fintech, InsurTech, Marketplaces.
- What check size does Rob Chaplinsky write?
- Rob Chaplinsky typically writes checks of $1M – $8M.
- Where did Rob Chaplinsky go to school?
- Rob Chaplinsky studied at Harvard Business School (MBA); University of Waterloo (BSC, Engineering).
Founder mafias
Harvard Business School mafia892
Also came through, then founded or led a company.
Tim DraperMBAFounded Draper AssociatesMike Maples JrMBAFounded Pattern BreakersHristo BorisovOPM Class 64Founded PayhawkNoubar AfeyanVisiting LecturerFounded ProFound Therapeutics +13Wade MyersMBAFounded RealManage +6Wade MyersMBAFounded RealManage +6
+ 885 more
University of Waterloo mafia346
Also came through, then founded or led a company.
Chamath PalihapitiyaB.A.Sc.Founded 8090Apoorva MehtaBAScFounded InstacartJon LernerBachelor of Applied ScienceFounded Textnow +2Michael LittBASc. Honours Systems Design EngineeringFounded Garage Capital +1Mike McCauleyBAScFounded Garage Capital +1Zach WaterfieldComputer EngineeringFounded Zettlor +1
+ 339 more
Link Ventures mafia5
Also came through, then founded or led a company.
Mohr Davidow Ventures mafia5
Also came through, then founded or led a company.
Loop mafia4
Also came through, then founded or led a company.
Same school
Also attended Harvard Business School2,000
Brad GerstnerFounder & CEO of Altimeter CapitalAileen LeeFounder & Managing Partner of Cowboy VenturesJim BreyerFounder & CEO of Breyer CapitalTim DraperFounder of Draper AssociatesMike Maples JrCo-founding Partner at FloodgateMamoon HamidPartner at Kleiner Perkins
+ 1,994 more
Also attended University of Waterloo541
Chamath PalihapitiyaFounder & CEO of Social CapitalApoorva MehtaFounder of Instacart; founder of Cloud Health SystemsAchintya ChaudhariInvestor at LightbankKarim GillaniGeneral Partner at Luge CapitalRohan MongaInvestment Associate at Luge CapitalAndrew MiklasGeneral Partner at Y Combinator
+ 535 more
Shared employers
Also worked at Caribou4
Also worked at Dryft1
Also worked at Proofpoint19
Dale ChangOperating Partner at Scale Venture PartnersDarren LeeInvestor at EPIC VENTURESJoe HorowitzManaging General Partner at Icon VenturesRob WardCo-Founder and Partner at Meritech Capital PartnersAbhijit SolankiFounder & Managing Director at Whiteboard Venture PartnersJohn DelaneyPrincipal at Greylock Partners
+ 13 more
Also worked at Rypple8
Daniel PortilloCofounder at General PartnershipEllen LevyFounder & Managing Director of Silicon Valley Connect at SignalFireSteve DeBaccoCo-Founder and Managing Partner at Leaders FundDavid SteinCo-Founder and Managing Partner at Leaders FundNick SteinCMO | GTM Advisor at Leaders FundTihomir BajicManaging Partner, X& at Leaders Fund
+ 2 more