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Flip

AI voice assistant for business support

Staff Software Engineer

Full-Time
$200k - $400k+ Equity
Senior
New York, NY, USA+1 moreMore locations: Marina Del Rey, CA, USA
In PersonOn-site five days per week.
Software EngineeringAI Application Engineering

About the job

Requirements
  • Real production experience building and owning systems where failures have consequences.
  • Sound judgment about what to ship, what to delay, and what not to ship, informed by production experience.
  • Ability to take ownership of outcomes and execute toward shipped results.
  • Customer-focused approach and willingness to engage closely with customer problems.
Responsibilities
  • Build AI agents that execute complex, multi-step customer workflows and integrate with contact-center systems and industry systems such as order systems, healthcare workflows, and logistics systems.
  • Build the platform orchestration layer used by agents, including routing, state, tool use, and reusable primitives for vertical teams.
  • Host models and build low-latency inference serving at production scale.
  • Build and maintain telephony, observability, and deployment infrastructure that supports live calls.
  • Work across customer-facing activities and complex backend systems, with placement and collaboration style determined together with the team.
Desired Qualifications
  • Python, MongoDB, AWS, Twilio, Datadog, Snowflake, and Omni experience.

About the company

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.

Company Size

51-200

Company Stage

Series A

Total Funding

$27.9M

Headquarters

New York City, New York

Founded

2015

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Simplify's Take

What believers are saying

  • Flip closed a $20 million Series A in January 2026, adding Next Coast and Ridge.
  • The company says it automates up to 90% of inbound calls, driving ROI.
  • Leadership hires Amy McDonnell and Lee Nadler on March 31, 2026, signal aggressive scaling.

What critics are saying

  • OpenAI Presence launched July 22, 2026, bundling enterprise voice, guardrails, and deployments.
  • Amazon Connect expanded agentic voice on July 20, 2026, with 50+ languages.
  • Flip depends on a narrow vertical niche; one platform misstep can erode trust fast.

What makes Flip unique

  • Flip focuses on retail, healthcare, and transportation, not generic customer-support automation.
  • By March 2026, Flip reported 300 million calls across 250+ enterprise customers.
  • Flip's 80+ native integrations and end-to-end call resolution deepen workflow stickiness.

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Benefits

  • Health Insurance
  • Unlimited Paid Time Off
  • Company Equity

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

-5%

2 year growth

-12%
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.

VCNewsDaily
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.

GlobeNewswire
Feb 11th, 2022
RedRoute Raises $6.5 Million in Seed Funding

The company will use the funds to expand leadership in the emerging $300 billion customer service automation space...