Flip

Flip

AI voice assistant for business support

About Flip

Simplify's Rating
Why Flip is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Data & Analytics

Enterprise Software

AI & Machine Learning

Healthcare

Company Size

51-200

Company Stage

Series A

Total Funding

$27.9M

Headquarters

New York City, New York

Founded

2015

Overview

Flip CX provides an AI-powered voice assistant for businesses, focusing on automating and improving phone-based customer service in retail, transportation, and healthcare. It handles common inquiries and tasks like order modifications, using integrated conversation flows, AI training, and system integrations to simplify adoption. The platform aims to deliver measurable improvements in customer experience metrics, retention, and cost savings, offering tangible performance insights to show the impact of its technology.

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Simplify's Take

What believers are saying

  • $20M Series A in January 2026 fuels 3x YoY growth to eight-figure ARR.
  • AI CSAT & Revenue Analytics launched for real-time retail CX insights.
  • Conversational calls handle transportation tasks like ride scheduling naturally.

What critics are saying

  • OpenAI GPT-4o outperforms Flip's voice AI in latency and accuracy.
  • Google Vertex AI displaces Flip using existing enterprise relationships.
  • $20M runway ends by Q4 2027 without Series B or profitability.

What makes Flip unique

  • Flip specializes in voice AI for retail, transportation, and healthcare verticals.
  • Deep integrations enable autonomous resolution of complex customer calls.
  • Processed 300 million calls, automating 90% of inbound volume for 250+ brands.

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Funding

Total Funding

$27.9M

Above

Industry Average

Funded Over

4 Rounds

Series A funding typically happens when a startup has a product and some customers, and now needs funding to scale. This money is usually used to grow the team, expand marketing, and improve the product. Venture capital firms are frequently the main investors here.
Series A Funding Comparison
Above Average

Industry standards

$15M
$8.2M
Discord
$15M
Canva
$20M
Flip
$30M
Kalshi

Benefits

Health Insurance

Unlimited Paid Time Off

Company Equity

Growth & Insights and Company News

Headcount

6 month growth

-7%

1 year growth

-3%

2 year growth

-7%
The Associated Press
Mar 31st, 2026
Flip appoints CCO and CMO after $20M Series A to scale Voice AI platform serving 250+ brands

Flip, an enterprise voice AI platform for retail, healthcare and transportation, has appointed Amy McDonnell as chief customer officer and Lee Nadler as chief marketing officer following its $20 million Series A round in January 2026. The New York-based company's platform replaces traditional phone systems with conversational AI that autonomously handles customer service calls. Flip has processed over 300 million calls for more than 250 enterprise customers, automating up to 90% of inbound call volume. Clients include Under Armour, Tory Burch and the NFL. McDonnell brings 25 years of customer experience leadership, whilst Nadler previously helped grow DoubleClick from startup to IPO and built MINI into a top 100 global brand. Flip is growing three times year-over-year and has reached eight-figure annual recurring revenue.

VC News Daily
Jan 14th, 2026
Flip Secures $20M Series A Financing Round

NEW YORK, NY, Flip, the AI solution that automates customer service calls for enterprise brands, today announced a $20 million Series A funding round co-led by Next Coast Ventures and Ridge Ventures.

Crunchbase
Jan 13th, 2026
Flip raises $20M Series A for vertical AI customer service across transport, retail and healthcare

Flip, a New York-based startup offering voice AI for customer service, has raised $20 million in a Series A round. The company develops AI that answers and automatically resolves routine customer requests for businesses. Founded in 2018 by CEO Brian Schiff and CRO Sam Krut, Flip initially focused on transportation companies before expanding into retail in 2021 and healthcare in 2024. The startup differentiates itself in the crowded AI-based customer service market through a vertical approach, concentrating exclusively on these three industries. The company aims to provide an Amazon Alexa-like voice AI experience for businesses, handling routine customer enquiries automatically.

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