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Christopher Lochhead
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Christopher Lochhead

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At a glance

Full Name
Christopher Lochhead
Title
Angel Investor / Advisor; Author & Podcaster; Co-Founding Partner, Play Bigger Advisors
Firm
Play Bigger Advisors (and personal investing via lochhead.com)
Firm Type
Angel Investor
Investment Stage
Seed / Angel rounds
Check Size
Angel-scale (individual checks within seed rounds; specific amounts not publicly disclosed)
Target Company Profile
Early-stage, venture-backed software and tech startups — frequently companies pursuing a "category design" / category-creation strategy
Sector Focus
Enterprise software / business productivity applications, SaaS, AI, and education/training services
Geographic Focus
United States, primarily Silicon Valley
Location
California (San Francisco Bay Area / Santa Cruz region), USA

Background

Christopher Lochhead is a former three-time Silicon Valley public-company Chief Marketing Officer, best known today as a "godfather" of Category Design, a bestselling author, and a charting business podcaster. Born in Montreal, Canada, he tells his own origin story as a dyslexic paperboy who was thrown out of school at 18 and, with few options, became an entrepreneur. He has since built a career at the intersection of marketing, company-building, and early-stage investing.

His operating résumé includes CMO roles at three public technology companies: Mercury Interactive, Scient, and Vantive. At Mercury Interactive — a roughly $1B enterprise-software company — he served as CMO; the company was acquired by Hewlett-Packard in 2006 for about $4.5 billion. These operating roles, centered on positioning and market creation, became the raw material for the discipline he later codified.

Lochhead co-founded Play Bigger Advisors and co-authored *Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets* (HarperCollins, 2016) with Al Ramadan, Dave Peterson, and Kevin Maney — the foundational book on "category design." He went on to co-author additional bestsellers including *Niche Down*, *Snow Leopard*, *A Marketer's Guide to Category Design*, and *The 22 Laws of Category Design*, and co-created the Category Pirates newsletter. He hosts the podcasts *Christopher Lochhead | Follow Your Different* and *Lochhead on Marketing*.

As an investor, Lochhead describes himself as an advisor, board director, and/or investor to 50+ venture-backed Silicon Valley startups, and a limited partner (LP) in several top-tier Silicon Valley VC funds. His angel activity skews toward enterprise applications and category-creating companies, and continues into recent years (his publicly recorded investments span from a 2015 seed round in Spiro through a 2023 investment in D'Skills).

Investment Thesis & Focus

  • Invests at the angel / seed stage in venture-backed startups, typically alongside other angels and institutional seed investors.
  • Primary sector tilt is enterprise applications / business-productivity software, with exposure to SaaS, AI, and education/training (B2C) companies.
  • Strong bias toward "category design" — companies that aren't trying to be "better" within an existing market, but are designing and dominating a *new* category. His stated worldview: escape the "better" trap, "dam the demand," and execute a "lightning strike" go-to-market.
  • Values differentiated positioning and narrative ("Follow Your Different"); founders who can articulate the *problem/category* they are creating, not just the product, are most likely to resonate.
  • Acts as a hands-on advisor/board member, not a passive check — he brings marketing, category, and go-to-market expertise to portfolio companies.
  • Also invests indirectly as an LP in Silicon Valley venture funds, in addition to direct angel checks.

Notable Investments

  • Spiro (Spiro.AI / Spiro Technologies) — Proactive relationship-management / AI sales-assistant platform; participated in Spiro's ~$1.5M seed (angel) round announced Nov 2015; listed as an advisor.
  • D'Skills — Education and training services (B2C) startup; recorded as one of his more recent investments (Sept 2023).
  • 50+ venture-backed startups — Broad portfolio of advisory/board/investor roles across Silicon Valley software companies (individual names not all public).

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