Headline

Headline is a multi-local, globally connected technology investor that leads Seed through Series A deals via regional funds and supports breakout companies through a worldwide Growth fund. The firm is strongly data-driven in underwriting, with product-market fit, retention quality, and global scaling potential carrying more weight than narrative or vanity growth.

Evaluation weights

How much weight this firm places on each dimension. Totals 100%.

Product-led · 30%

Metrics

24%

Revenue, growth, and unit economics

Market

28%

Size, timing, and competitive landscape

Team

18%

Founder experience and execution ability

Product

30%

Differentiation and technical quality

Favors measurable PMF over founder charisma
Strong bias toward retention and cohort evidence over vanity growth
Prefers businesses that can scale internationally through local-to-global expansion
Will take early risk, but only when the data suggests durable fundamentals

Pitch difficulty

How hard it is to get a meeting and close funding from this firm.

Funded / yr

Deals closed in a typical year.

Led / yr

Rounds led in the last 12 months.

Pitches / yr

~23192

Decks reviewed in a typical year.

Acceptance rate

0.2%

Share of pitches that get funded.

Estimated — public data is not fully disclosed.

Why it's hard

Retention and NDR are central gating criteria
The firm prefers lead positions and conducts data-heavy underwriting
Weak ICP clarity or shallow engagement is a common deal-breaker
Global ambition and cross-border scalability are important filters

Headline is aggressive at Seed and Series A and has meaningful global reach, but its bar on PMF evidence, retention quality, and disciplined scaling is notably high. Companies with strong narrative but weak cohort data are unlikely to pass.

Green flags

What drives a yes for this firm.

Clear product-market fit evidenced by strong retention and cohort quality
High Net Dollar Retention, deep usage, and healthy unit economics
A large market undergoing digitization with room for international expansion
Founders showing a leader mindset and ambition to build globally
A crisp ICP and disciplined scaling motion rooted in sustainable growth

Red flags

What kills deals and gets a fast no.

Low or deteriorating retention and NDR
Unclear ICP or weak evidence of true product-market fit
Growth that is primarily bought through marketing spend
Scaling headcount or burn ahead of validated demand
Cultural misalignment or hype-first storytelling unsupported by fundamentals

How to win

Patterns that lead to successful pitches.

Show cohort-level retention, NDR, usage depth, and unit economics in a crisp, data-backed way
Demonstrate a sharply defined ICP and why the product is mission-critical for that customer
Frame the company as a local winner with credible cross-border expansion potential
Present disciplined growth rather than paid-spend-fueled top-line inflation
Show founders have both conviction and operational maturity around responsible scaling

Fund strategy & identity

Who they are and how they operate.

Lead Seed and Series A rounds locally in North America, Europe, LatAm, and Asia-Pacific
Use proprietary tools like Deepdive, Searchlight, EVA, and ATHENA to source and validate outliers
Double down in Series B+ and Growth when PMF, retention, and unit economics are proven
Back large digitizing markets where software, fintech rails, AI, or network effects can travel internationally
Avoid businesses scaling ahead of PMF or relying on weak economics and hype-driven demand

Firm identity

Multi-local venture platform with autonomous regional fundsGeneralist tech investor with strong software, AI, fintech, and marketplace pattern recognitionRetention- and cohort-driven underwriter using proprietary analytics toolsLead-oriented early-stage investor with follow-on capacity through a global Growth fundCross-border scaling partner for companies with global ambition

Investment focus

Industries, themes, and typical ARR expectations.

Industries

Enterprise SoftwareAI/MLAI InfrastructureFintechVertical SaaSConsumer InternetMarketplacesDeveloper ToolsData InfrastructureHardware

Investment themes

AI infrastructure and core software platformsVertical SaaS with strong cohort behavior and durable retentionFintech infrastructure and embedded financial railsConsumer and B2B marketplaces with network effectsCross-border platforms that can scale across regionsDeveloper tools and data infrastructureSelective hardware-software hybrids with ecosystem leverage

Typical check by stage

Seed$1M-$5M

Series A$5M-$15M

Series B$20M-$70M

Series C$20M-$70M

Growth$20M-$70M

Typical ARR by stage

Seed$0-$1M

Series A$1M-$5M

Series B$5M-$20M

Growth$20M+

Investment thesis

Core beliefs and strategy behind their investing approach.

Headline is a general‑ist early‑stage tech investor that pairs a multi‑local entry model with a global growth fund. Its sector focus centers on software and infrastructure (including AI), fintech, consumer marketplaces, and vertical SaaS. Geographically, autonomous funds operate in North America, Europe, Brazil/LatAm, and Asia‑Pacific, allowing local teams to lead Seed‑Series A deals while the Growth fund backs Series B+ rounds worldwide. The firm believes value is created when founders anywhere receive local conviction plus cross‑border scaling support, underpinned by data‑driven underwriting. Headline’s proprietary tools (Searchlight, Deepdive, EVA, ATHENA) screen millions of companies to surface outliers and benchmark retention and unit economics. The firm avoids businesses with poor retention/NDR, undefined ideal customer profiles, or those that chase hype without sustainable economics. It also steers clear of overly capital‑intensive hardware‑only models lacking clear path to scale.

Decision patterns

How they evaluate and make investment decisions.

Headline invests when there is clear evidence of product‑market fit and high‑quality cohorts. The firm relies heavily on retention metrics such as Net Dollar Retention (NDR), usage depth, and unit economics, using its Deepdive analytics to validate these signals. Founders must exhibit a "leader mindset" and a willingness to build globally. Market selection favors large, digitizing verticals where software, AI, fintech rails, or network effects can scale across borders. While exceptional teams are valued, they will not compensate for weak PMF; retention and cohort quality outweigh vanity growth. Deal‑breakers include low or deteriorating NDR, unclear ICP, shallow engagement, scaling ahead of PMF, growth driven mainly by paid spend, and cultural mis‑alignment.

Risk appetite

Headline exhibits a medium‑to‑high risk appetite. It aggressively leads Seed and Series A investments across its regional funds, then often doubles down in later rounds through its Growth fund when fundamentals are validated. The firm’s methodology is data‑grounded, enforcing strict PMF and retention thresholds, which tempers the aggressiveness. Deployment cadence is disciplined (roughly three‑year fund life), and the firm prefers to lead but will co‑lead when strategic fit aligns.

Notable investments

Key portfolio companies and why they fit the thesis.

Heidi HealthLead
AI‑first clinical documentation platform that aligns with Headline’s data‑driven, early‑stage AI thesis.
Blossom HealthLead
AI operating system for psychiatry; fits Headline’s focus on tech‑enabled healthcare and strong founder‑market fit.
NotchLead
AI infrastructure for regulated industries; matches Headline’s interest in enterprise AI with clear unit economics.
DideroLead
AI‑driven procurement platform (vertical SaaS) that supports Headline’s enterprise‑AI thesis; co‑led the round.
Owner.comLead
Restaurant operating system scaling to category leadership; demonstrates Headline’s ability to co‑lead growth‑stage rounds.
AiPriseLead
Global KYC/KYB orchestration fintech; aligns with Headline’s focus on cross‑border compliance and infra SaaS.
StotlesLead
Public‑sector revenue platform (vertical SaaS) that fits Headline’s data‑rich workflow thesis; co‑led the round.
NetBox Labs
Open‑source infrastructure management tool; Headline participated in a Series B but did not lead, illustrating selective growth‑stage participation.

Co-invested with

Other firms in this catalog who've backed the same companies.

Two Sigma Ventures
NetBox Labs

Partners

Full firm roster — key partners, partners, and the wider team.

Key partners

Mathias Schilling

Co-Founder and Managing Partner

Headline

Co-Founder and Managing Partner at Headline, associated with software, SaaS, consumer, and recent healthcare AI investing.

Application software / SaaSConsumer

Thomas Gieselmann

Founding Partner

Headline

Founding Partner at Headline, associated with software, infrastructure, developer tools, open source, fintech, and compliance automation.

AICloudDeveloper toolsInfrastructure software

Christian Miele

General Partner

Headline

General Partner at Headline in Berlin, focused on software and deep tech.

Deep techSoftware

Christian Leybold

Founding Partner

Partner

Headline

Tokyo-based Headline Partner investing in consumer internet, fintech and SaaS.

Consumer internetE-commerceFintechSaaSWeb3

Team

Jennifer Lin

Investor

Headline

Taipei-based Headline investor focused on enterprise, InsurTech, real-estate tech and consumer.

AsiaConsumerEnterprise solutionsInsurTechReal-estate tech

Linda Brosig

Growth Investor

Headline

London-based Headline growth investor focused on European growth-stage companies.

Cross-sector investingEuropean growthGrowth equity

Santiago Rallo

Investor

Headline

Headline investor focused on workflow optimization and business-efficiency software.

Business efficiencyEarly stageUnderserved marketsWorkflow software

Luis Schmitz

Investor

Headline

Early-stage Headline investor focused on analytics, automation, and AI.

AIAnalyticsAutomationEarly stageProcess software

Paula Daniela Carneiro

Headline

Headline investor focused on SaaS, founder-startup fit, and durable customer relationships.

B2B technologyCustomer retentionFounder-startup fitInvestment researchSaaS

Pietro Caiafa

Investor

Headline

São Paulo-based Headline investor focused on fintech, SaaS, energy, and sports.

EnergyFintechLatin AmericaSaaSSports

Public voice

Notable statements and public positions.

“Markets like these reward creativity, decisiveness, and the anti‑sheep. Today, courage and conviction will be the most critical currencies.” – Mathias Schilling, co‑founder (US)
“Despite the recent market shifts, we continue to aggressively pursue the next wave of world‑changing innovation… with a measured, methodical approach to investment that relies on our homegrown technology.” – Mathias Schilling, TechCrunch interview
“We believe in responsible investing and scaling. Founders must have a clear understanding of their product‑market fit and the potential for sustainable growth. Deepdive helps founders quantify and visualize product‑market fit…” – Thomas Gieselmann, co‑founder (EU)
“Early‑stage valuations are still where the most outsized returns are made… We are very much interested in global startups coming out of Asia.” – Akio Tanaka, partner (Asia)

Similar firms

Firms with overlapping stage and industry focus.

Headline

Evaluation weights

Pitch difficulty

Green flags

Red flags

How to win

Fund strategy & identity

Investment focus

Investment thesis

Decision patterns

Risk appetite

Notable investments

Co-invested with

Partners

Mathias Schilling

Thomas Gieselmann

Christian Miele

Christian Leybold

Conrad Chu

Michel de Lavit

Lauren Lyon

Romero Rodrigues

Clarey Zhu

Taylor Brandt

Jonathan Becker

Jonathan Userovici

Trevor Neff

Shalini Rao

Andreas Haug

Gabriel Alves

Nancy Xiao

Akio T.

Jennifer Lin

Linda Brosig

Santiago Rallo

Luis Schmitz

Paula Daniela Carneiro

Victor Toledo Soares Cintra

Valentin Kremer

Isamu Nishijima

Jake Horwitz

Anna Faulkner

Cyprien Benoist

Ketul Patel

Jacob Conger

Adeyinka Okuwoga

Jerry Fung

Astrid Moullé-Berteaux

Kiran Modi

Jeremy Kai P.

Savanna Silver

Matthew Brown

Nicolas von Blottnitz

Pietro Caiafa

Public voice

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