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    Lookout Ventures logo

    Lookout Ventures

    Washington, District of Columbia, United StatesFounded 2024
    www.lookoutventures.comLinkedIn
    SaaSCybersecurityData & Analytics

    Lookout Ventures is a Washington, DC-based venture capital firm that backs early-stage B2B software companies in overlooked US geographies. The firm invests from pre-revenue to $1M ARR, writing checks of $500K to $2M at the seed stage with a focus on SaaS, cybersecurity, and infrastructure software.

    43% of their portfolio is in Cybersecurity. They made 1 investment in the last 12 months. Their most common stage is seed (43% of deals). Average disclosed round size is $6.7M (across 6 rounds with reported amounts).

    Find people at Lookout Ventures on Goldilocks AI

    Portfolio

    6

    Fund Size

    $30M

    Top Stage

    Seed

    Last 12 Mo

    1

    Team

    Matt Bressler

    Matt Bressler

    General Partner at Lookout. Previously at TDF Ventures and GE Ventures. Recovering management consultant.

    Will Rayner

    Will Rayner

    General Partner at Lookout. Previously at TDF Ventures and Accion Venture Lab. Recovering management consultant.

    LT

    Lei Tung

    Product and engineering executive, principal architect at Marketo ($1.8B exit)

    Jim Pastoriza

    Jim Pastoriza

    Chairman at Lookout. 25 year venture career across TDF Ventures, JPMorgan Capital, and AT&T Ventures. Ex-operator at AT&T and Lucent.

    DA

    Dennis Ainge

    GTM and data strategy expert, founding executive at TARGUSinfo (>$500M exit)

    JS

    John Schanz

    Hyperscale technology and operations leader, formerly Chief Network Officer roles at Comcast and AOL

    RB

    Randy Brouckmann

    Multi-time CEO, most recently EdgeConnex in data center / cloud infrastructure space (multi $B exit)

    SM

    Steve Mankoff

    Ran Customer Success, Support, Education, Professional Services, Q&A, and Offshore Dev + member of Founder’s Circle at Siebel Systems (IPO)

    TK

    Tiffany Kleemann

    SaaS and cybersecurity CEO & sales leader, background in White House & US military

    Portfolio Breakdown

    Stage Distribution

    Sector Distribution

    Investment Activity

    DealsAvg Round Size

    Portfolio

    7 investments
    CompanyRoundAmountDate
    Verisoul logoVerisoulSeries A$9MDec 2025
    Trustible logoTrustibleSeed$4.6MJan 2025
    Saleor logoSaleorSeed$2.5MMar 2021
    Contego Medical logoContego MedicalSeries B$5.6MJan 2015
    Arpio logoArpioSeries A$15M—
    LLemhiPre-Seed——
    Verisoul logoVerisoulSeed$3.3M—

    Top Co-Investors

    BITKRAFT Ventures2 shared
    King River Capital2 shared
    Cherry Ventures1 shared
    Vercel1 shared
    Third Prime1 shared
    High Alpha1 shared
    Paladin Capital Group1 shared
    Y Combinator1 shared
    Valor Equity Partners1 shared
    S3 Ventures1 shared
    Uncorrelated Ventures1 shared
    CreativeCo Capital1 shared
    Draper Associates1 shared
    U.S. Venture Partners1 shared
    Mountain Group Partners1 shared
    Top Down Ventures1 shared
    Tau Ventures1 shared
    Alumni Ventures1 shared
    Harlem Capital1 shared
    Inner Loop Capital1 shared

    Last updated: 27 September 2026