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Headsup

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Empowering sales teams in product-led companies with data

San Francisco, United StatesFounded 2020Marketing
Valuation $25–50M Last recorded · 2022
Revenue $1–10M Latest reported FY
Headcount <100 Current team size
Total funding $10–50M Disclosed equity funding
Unlock exact values This page shows ranges. Dealroom has the exact numbers for Headsup and the history behind them.

About Headsup

HeadsUp.ai is a cutting-edge startup that operates in the customer relationship management (CRM) and sales enablement market. The company provides a browser extension that integrates seamlessly with popular CRM platforms like Salesforce and HubSpot. This tool allows sales teams to access crucial product usage data directly within their existing workflows, enabling them to make data-driven go-to-market (GTM) decisions. By offering visibility into key conversion indicators and insights on power users and decision-makers, HeadsUp.ai helps sales representatives customize their outreach efforts more effectively.

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The primary clients of HeadsUp.ai are enterprise-level businesses that require sophisticated data handling and integration capabilities. These clients benefit from the platform's ability to pull data from various sources, unify it, and write it back to their data warehouses. This ensures that all stakeholders can focus on their specific roles without worrying about data fragmentation or security issues.

HeadsUp.ai operates on a subscription-based business model, charging clients a recurring fee for access to its platform. The company makes money by offering different pricing tiers based on the level of service and features required by the client. This model ensures a steady revenue stream while allowing clients to scale their usage as needed.

One of the standout features of HeadsUp.ai is its no-code lifecycle orchestration capability. This allows businesses to configure customer outreach across multiple channels from a single interface, driving maximum efficiency without the need for additional engineering resources. The platform supports marketing automation, sales efforts, and in-product nudges to accelerate customer activation, monetization, and expansion while preventing churn.

Security is a top priority for HeadsUp.ai, which is SOC 2 Type II certified and compliant with GDPR and CCPA regulations. The platform routinely passes data security reviews from large public companies, ensuring that client data is handled with the utmost care.

Source: Dealroom company data

At a glance

Status
Acquired
Founded
2020
Headquarters
San Francisco, United States
Employees
6
Open positions
None listed
Dealroom signal
59.6/100
Industry
Marketing
Sub-industry
CRM & Sales
Sector
Marketing
Technology
Artificial Intelligence
Business model
SaaS
Client focus
b2b

Funding history

3 recorded events

Company financing events and reported valuations.

Deal typeDateAmountValuationInvestorsSource
ACQUISITION✓Exit Nov 2023 $0 — Hightouch | Carry Technologies ↗
SEED✓Equity / VC Sep 2022 $8.5M $34M Spencer Crawley · Sam Endacott · Character · Lexi Quirk ↗
Showing the latest 2 of 3 recorded eventsBook a demo for the full funding history →

Financials

Revenue over time

Revenue, earnings and other financial measures where available. Years marked “E” are estimates.

YearRevenueGrowth
2026
2025
2024
2023
2022
2021 —
Company filings, research estimates and Dealroom dataBook a demo for the full financial model →

Growth signals

Headsup website traffic

Latest recorded traffic for Headsup is 770 monthly website visits, down 40.8% over the last three months. Headsup's team declined 66.7% over the past year.

Latest monthly visits770 3-month web change-40.8% 1-year team growth-66.7%
Summary metrics are public; monthly history is available with a demoCompare with peers →

Investments and acquisitions

Capital deployed

Recent portfolio relationships for companies that also act as investors or acquirers.

Investors

22 investors on the cap table

From Dealroom's funding and investor records, grouped by the round each investor first entered.

Seed17 investors entered at this stage

  • Class 5 Global
  • 645 Ventures
  • Phoenix Investment Club
  • Rankin Ventures
  • Firstminute Capital
  • CharacterVC
  • Spencer Crawley
  • Sam Endacott
  • Character
  • Lexi Quirk
  • Alessio Fanelli
  • Wing Venture Capital
  • Zachary Dewitt
  • Aaron Holiday
  • John Zeratsky
  • Vardan Gattani
  • Eli Blee-Goldman

Other known investors5 additional known investors

  • Hightouch | Carry Technologies
  • Business Angels Des Grandes Ecoles
  • firstminute
  • Joel A.
  • Joel Ayala
Team profiled 5 named & role-tagged
Founders Hidden — book a demo/100 quality score
Key operators 1 quality Hidden — book a demo/100
Potential founders Hidden — book a demo likely future founders
Startup mafia Hidden — book a demo alumni-founded startups
Talent movements Hidden — book a demo in · Hidden — book a demo out past 12 months

Source: Dealroom Talent Intelligence.

Global footprint

Workforce and web traffic by country
Workforce by country
1 countries with
team presence
🇺🇸 United States100%
1 country shown

Market sentiment

Posts on X, past 7 days

An AI-synthesised read of the highest-engagement posts about Headsup on X, ranked by likes and reposts, corporate channels excluded.

Reading the room on X — pulling top posts and synthesizing themes…

Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour

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