Headline — Investment Thesis & Preferences

Headline VC Research Document

Investment Thesis

Headline is a global venture capital firm that invests across multiple stages and sectors, with a core focus on finding disruptive founders building the next generation of technology companies. The fund's primary thesis centers on identifying "top founders everywhere" and providing them with capital, operational expertise, and a truly global platform to scale. Headline emphasizes a data-driven investment approach combined with deep hands-on operational support through specialized teams for talent, brand, technology, and market access.

Sector Focus

Headline takes a broadly diversified approach across multiple sectors, with particular strength in:

Commerce Enablement Technologies - E-commerce infrastructure, B2B and consumer marketplaces, go-to-market technologies, sales enablement, marketing enablement, and marketplace platforms
Software Infrastructure - Developer tools, observability, monitoring platforms, data infrastructure, CI/CD systems, and enterprise productivity tools
Fintech & Payments - Financial services platforms, payment systems, banking infrastructure, robo-advisory, financial wellness, and consumer finance
Consumer Apps & Commerce - Direct-to-consumer platforms, consumer marketplaces, luxury retail, grocery delivery, instant delivery services
Gaming & Entertainment - Game development, game publishing, streaming platforms, content distribution, and interactive entertainment
Healthcare & Wellness - Digital health platforms, fertility technology, wellness products, nutraceuticals, and healthcare infrastructure
Media & Entertainment - News platforms, podcasts, audiobooks, content creation and distribution, social networks
Enterprise Software - Workflow optimization, CRM integration, ERP systems, marketing automation, field service management
Real Estate & PropTech - Construction digitization, real estate marketplaces, property management technology

The fund maintains a diversified portfolio across industries, geographies, and stages rather than focusing on a single vertical.

Stage Focus

Headline operates across multiple stages with a structured approach:

Early Stage Fund: Invests in seed and pre-seed stage companies with hands-on support from dedicated regional teams
Growth Fund: Invests $20M+ in later-stage companies (Series B/C and beyond) with established product-market fit and global ambition
Multi-stage approach: The fund is not limited to any single stage but maintains active deployment across seed through growth stages

Check Size

Based on portfolio evidence and operational structure:

Early Stage (Seed): $2M-$5M typical range
Growth Stage (Series B/C+): $20M+ per investment
Fund Structure: Dedicated Growth Fund making larger checks alongside Early Stage regional funds
Portfolio sizing: Data suggests early stage checks in $2M-$4M range based on portfolio company valuations

Lead Tendency

Headline actively leads rounds across both early and growth stages. The fund positions itself as a lead investor at seed stage with significant ownership stakes. Evidence from portfolio company disclosures shows lead positions and meaningful board presence.

Recent Activity

Headline is actively deploying across all stage and geographies:

38+ portfolio companies currently managed
Multiple exits: Pismo (acquired by Visa), Segment (acquired by Twilio), Axios (acquired by Cox Enterprises), Scopely (acquired by Savvy Games Group)
Public company portfolio: Farfetch (NYSE: FTCH), SEMrush (NYSE: SEMR), Sonos (NASDAQ: SONO), Bumble (NASDAQ: BMBL), Angi (NASDAQ: ANGI), The RealReal (NASDAQ: REAL)
Continuous fund raising and deployment activities
Strong exit velocity with unicorn-level outcomes
Last known research update: January 2026 (recent)

Fund Status

Headline is actively deploying:

Growth Fund making substantial investments in later-stage companies
Early Stage Funds active in all major regional markets
Continuous portfolio company support through specialized teams
No indication of fundraising distraction or between-funds status

Portfolio Highlights

Exit Successes:

Pismo (acquired by Visa) - Fintech payments platform
Segment (acquired by Twilio) - Customer data platform
Axios (acquired by Cox Enterprises) - Media/news platform
Scopely (acquired by Savvy Games Group) - Game publisher

Public Companies:

SEMrush (NYSE: SEMR) - Marketing technology
Sonos (NASDAQ: SONO) - Consumer audio
Bumble (NASDAQ: BMBL) - Consumer social
Angi (NASDAQ: ANGI) - Home services marketplace
The RealReal (NASDAQ: REAL) - Luxury resale
Farfetch (NYSE: FTCH) - Luxury fashion marketplace

Active Portfolio (38+ companies): Mistral AI (infrastructure), Honeycomb (observability), Bitwarden (cybersecurity), Nivoda (fashion marketplace), Housecall Pro (field service), Staffbase (employee engagement), Creditas (fintech), Fetch (loyalty), Acorns (fintech), Raisin (fintech), Numa (consumer), Gopuff (instant delivery), Grüns (wellness), Bioptimus (biotech), Brite Payments (fintech), Natural Cycles (fertility), Homa (gaming), Owner (software), Motion (software), Air (software), Plancraft (software), and others.

Team

Headline operates as a global partnership with 60+ team members across continents:

Early Stage Investment Leaders:

Taylor Brandt (San Francisco) - Commerce enablement focus
Thomas Gieselmann (San Francisco)
Mathias Schilling (San Francisco)
Matt Brown (San Francisco)
Jacob Conger (San Francisco)
Nikki Farb (San Francisco)
Jerry Fung (San Francisco)
Ketul Patel (San Francisco)
Santiago Rallo (San Francisco)

Regional Leaders:

São Paulo: Gabriel Alves, Pietro Caiafa, Daniela Carneiro, Victor Cintra, Romero Rodrigues
Berlin (Major Hub): Jonathan Becker, Elias Börgmann-Dehina, Andreas Haug, Christian Leybold, Isabel Wrubel, Thilo Wurst, Christian Miele, Valentin Kremer, Martina Mattersberger
Paris: Cyprien Benoist, Astrid Moullé-Berteaux, Jonathan Userovici, Estelle Mamane
London: Linda Brosig, Michael Kent, Kiran Modi, Anna Faulkner, Dominic Wilhelm
Asia-Pacific: Tatsuya Kawamura, Yuka Kawata, SungJae Lim, Jennifer Lin, Akihiko Okamoto, Joseph Huang, Claire Liau, Jeremy Kai Proctor, Tomokazu Okada, Akio Tanaka, Isamu Nishijima, Toshiaki Shimakawa, Brian Yen, Jackson Loo

Specialized Teams:

Operations & Finance: Pat Reilly (CFO), Conrad Chu (CTO), Christine Betar (Fund Controller), Jack Dailey (Fund Controller), Calogero Sutera (Fund Controller)
Talent & People: Sean Cloney (Head of Talent), Oanh Eng (Fund Operations)
Legal & Compliance: Beverly Cheung, Elias Börgmann-Dehina, Viktor Gorlow, Wenceslas Moussa (Head of Risk & Compliance), Thilo Wurst, Alina Heiliger
Brand & Marketing: Molly Martell (Head of Brand), Guillaume Defer (Marketing Director), Ines Kopácsi (Senior Growth Marketing Manager), Enji Enkhbayar (Marketing & Community Manager)
Investor Relations: Estelle Mamane (Head of Investor Relations Europe), Lara Tricarico (Investor Relations Officer), Sean Watari (Investor Relations Associate)

The team reflects deep global coverage with dedicated investor teams on the ground in all major startup ecosystems and substantial operational support infrastructure.

Decision Process

Headline operates through a distributed partnership model with regional autonomy:

Regional investors make investment decisions for their markets with local expertise
Data-driven evaluation using proprietary internal tools for product-market fit assessment
Global capital allocation coordinated through San Francisco headquarters
Collaborative approach between early stage and growth stage teams
Investment committee review for larger or strategic investments

Geographic Focus

Headline maintains a truly global footprint with permanent teams in:

North America: San Francisco (headquarters), New York area
Europe: Berlin (major hub), London, Paris, Luxembourg
South America: São Paulo (major hub)
Asia-Pacific: Tokyo (major operations), Singapore, Taipei, Seoul

The fund is explicitly global in strategy and maintains permanent on-the-ground teams to source, evaluate, and support portfolio companies in each major region.

Founder Preferences

Headline seeks founders who are:

Disruptive and ambitious with global ambitions
Data-driven and analytical in approach
Willing to implement feedback rapidly from customers, investors, and advisors
Capable of building strong teams and attracting talent before funding
Domain experts with track records of scaling
Operators who understand growth mechanics, customer acquisition payback, and retention metrics
Leaders with proven ability to develop conviction through customer conversations

Investment Approach

Headline's investment philosophy emphasizes:

Data-Driven Diligence: Proprietary tools to assess product-market fit, growth trajectories, and customer segmentation
Operational Support: Hands-on help with Go-to-Market, talent hiring, brand building, and technology infrastructure
Global Platform Access: Real connections to advisors, customers, and markets across all regions
Long-Term Partnerships: Commitment to "go to the ends of the earth" to support portfolio success
Specialized Teams: In-house expertise for brand, talent, technology, and capital markets navigation