Jackson Square Ventures Research
Investment Thesis
Jackson Square Ventures (JSV) is an all-partner venture capital firm based in San Francisco's Jackson Square neighborhood, founded in 2011 as Sigma West before rebranding to reflect its ties to the local community. The firm believes "the future belongs to those who build" and positions itself around convening and connecting the next generation of AI-native founders. JSV invests almost exclusively in software and marketplace companies, with an increasing emphasis on AI-native businesses. All partners are former founders or senior tech operators, and the firm leans on that operating experience — go-to-market, enterprise sales, product, and IT buyer perspective — to support portfolio companies beyond capital.
Stage Focus
JSV's stated focus is Seed and Series A, though secondary sources describe the firm as stage-agnostic from pre-seed through Series B+ when following on in existing portfolio companies. In practice, recent deals span pre-seed (GitLaw, Provenance) through Series A (Clarity Pediatrics), with the firm typically acting as lead investor at the earliest institutional round.
Check Size
Typical check size ranges from $100K to $5M, with a stated sweet spot around $1.5M for initial checks. The firm reserves capital for follow-on participation in later rounds of its strongest portfolio companies.
Lead Tendency
JSV frequently leads. Of the last several disclosed rounds, the firm led Cloverleaf AI's $2.8M seed (November 2024), GitLaw's $3M pre-seed (November 2025), Clarity Pediatrics' $14.5M Series A (December 2025), and Provenance's pre-seed at a $20M valuation (June 2026).
Recent Activity
JSV's current fund is reported at $245M, with total capital deployed exceeding $700M across at least four funds since 2011. Public trackers estimate total AUM around $380M. The firm made roughly 5 new investments in 2025 and has continued deploying into 2026:
- June 2026: Led Provenance's (ProvenanceXL) pre-seed at a $20M valuation, alongside Glasswing Ventures. Provenance builds AI-native audit-trail and version-control infrastructure for financial models used by investment banks and PE firms.
- December 2025: Led Clarity Pediatrics' $14.5M Series A, backing a virtual pediatric chronic-care platform (ADHD, anxiety, and expanding into obesity care), alongside City Light Capital, MassMutual Catalyst Fund II, GingerBread Capital, Scrub Capital, and Operator Collective.
- November 2025: Led GitLaw's $3M pre-seed, an AI legal-contract agent for startups and SMBs, alongside Flex Capital and Background Capital.
- November 2024: Led Cloverleaf AI's $2.8M seed, a government-contracting intelligence platform, alongside First Mile, Techstars, and Legal Tech Fund.
Portfolio Highlights
JSV has backed more than 60 companies across its funds, producing 4 unicorns and roughly 50 exits. It was a principal early investor in DocuSign and Upwork, both of which achieved NASDAQ IPOs. Other notable portfolio companies include Strava, Seismic, OfferUp, The Athletic (acquired by The New York Times), Alto Pharmacy, Jackbox Games, Intacct (acquired by Sage), Centrify, AlienVault (acquired by AT&T Cybersecurity), Demandbase, CREXi, Trust & Will, and Plume. Several portfolio companies have gone through notable exits, including EqualLogic (acquired by Dell), Hightail, and Contently.
Team
- Greg Gretsch — Managing Director & Founding Partner. Two decades in venture capital, focused on category-leading software companies; notable investments include Strava, Upwork, and Jackbox Games, with five early-stage investments exceeding $1B in exit value or valuation.
- Pete Solvik — Managing Director & Founding Partner. Former CIO of Cisco during its growth from a fraction of its size to $20B in annual sales; previously an 11-year IT executive at Apple overseeing Apple Online Services. Deep enterprise-software buyer perspective.
- Bob Spinner — Founding Partner & Managing Director. Early operating executive at three startups (Sales Director at Sybase, SVP Sales at Clarify, CEO at Extensity); focuses on cloud applications, security, and big data, with a go-to-market specialty.
- Victor Echevarria — Managing Director. Joined JSV in 2018 after ten years founding and operating early-stage companies; focuses on digital health, fintech, labor marketplaces, and enterprise SaaS. BS Electrical Engineering (UC Berkeley), MBA (Harvard Business School).
- Dan Preston — Venture Partner. Former CEO of Metromile (NASDAQ: MILE, later acquired by Lemonade); co-founder/CTO of AisleBuyer (acquired by Intuit, 2012). BS Computer Science (Brandeis), MS Computer Science/Machine Learning (Stanford).
- John Otterson — Operating Partner & Investor Relations. Joined 2015; 25 years in the innovation sector, including 15 years leading LP relations for SVB Capital. Co-founded EvoNexus (San Diego) and MaiTai (Maui) startup communities.
- Johnny Brackett — Portfolio Marketing. Nearly 15 years of marketing experience, including PR agency work and startup operating roles at Block, TaskRabbit, and Shyp; named to PRWeek's Innovation 50.
- Kathleen Connolly — Operations.
- Denise Soucie — Operations.
Decision Process
JSV is structured as an all-partner firm; investment decisions run through its partnership of founding and managing directors rather than a single solo GP or large investment committee.
Founder Preferences
JSV favors technical and operator founders building software or marketplace businesses, with a growing preference for AI-native product architectures. The firm's Launchpad accelerator (a 10-week summer program with a $35,000 SAFE investment) and Venture Scouts education program suggest a preference for engaging founders early, sometimes pre-formal-fundraise.
Geographic Focus
Primarily United States, with a strong Bay Area/San Francisco concentration reflecting the firm's roots in the Jackson Square district, though portfolio companies span the US broadly (e.g., Denver-based Cloverleaf AI) and internationally (UK-facing GitLaw, Turkish-founded Provenance).
Community Programs
Beyond capital, JSV runs several founder-facing programs: Book Club (a 250+ member community of founders, CEOs, and LPs), Startup Ride (a weekly founder-investor cycling event), Venture Scouts (a venture capital education program), and Launchpad (a 10-week summer accelerator with a $35,000 SAFE).