Full-Time

Enterprise Customer Success Lead

Posted on 10/3/2025

Flip

Flip

51-200 employees

AI voice assistant for business support

Compensation Overview

$110k - $150k/yr

+ Bonus + Commission + Equity

Culver City, CA, USA + 1 more

More locations: New York, NY, USA

In Person

Category
Sales & Account Management (1)
Required Skills
Sales
Marketing
Requirements
  • Startup experience and have seen a company scale their customer success from +10 clients to hundreds. Understand what it takes to build teams and implement scalable systems for long term success
  • +5 years of experience leading a CS function for a B2B software company
  • Strong communication skills both in-person and virtually between internal teams, client partners, stakeholders by embracing ownership. Ability to understand the why and persuasively communicate messaging for internal and external buy-in
  • Eager and willing to support your teammates - just like they will with you! Player-coach when it comes to developing a team of highly motivated individual contributors
  • Either already are or become obsessed with eCommerce customer experience/support
  • Go above and beyond consistently
Responsibilities
  • Make sure our reference list is as long as our customer list…
  • Make Flip the impactful tool in the tech stack for our customers, i.e. deliver business impact through our product, identify the problems they’re looking to solve, configure our product to optimize performance, and collaborate with our product team to constantly raise the roof
  • Be our customers’ favorite vendor to work with - build authentic, trust-based relationships where every interaction leaves clients feeling heard, supported, and excited about what’s possible. Expand our network of champions across all relevant stakeholders. Get on airplanes to meet them in person
  • Support prospects in evaluating our product, then lead implementation all the way through the lifetime of the relationship
  • Go above and beyond for their requests - make the extra test call, solve edge cases, and deliver outcomes customers didn’t even realize were possible
  • Become a product and domain expert quickly *(within week 1)* - master Flip’s platform (either ecom/retail or healthcare) workflows so you can configure, troubleshoot, and advise with authority
  • Unpack their problems and dig into the “why” - get past surface level issues to uncover root causes
  • Liaise with our product teams to craft solutions - translate client needs into clear feedback that shapes our roadmap and strategy
  • Storytell with data - use metrics to show how Flip meets their goals, gives great patient experiences and delivers clear ROI
  • Partner with sales - work side-by-side to accelerate launch and automation through customer success, making Flip the reason they choose us and the reason they grow with us
  • Coach and scale the CS team - hire, mentor, and empower exceptional CSMs while raising the bar for execution and culture. Initially this role will be an IC for first ~6 months
  • Collaborate with marketing to bring new customers into our community by helping current customers share their story
Desired Qualifications
  • Experience building customer success processes in both startup and enterprise contexts.
  • Passion for storytelling and community building - helping customers share wins publicly.
  • Previous experience with Healthtech company during its early stages, a-b-c
  • Familiarity with EHR/PM integrations (Epic, Athena, Experity, eClinicalWorks, etc.) and healthcare data standards (HL7, FHIR, HIPAA).
  • Strong understanding of payer/provider dynamics, patient experience workflows, and healthcare compliance considerations.

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

Simplify Jobs

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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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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