Flip
Flip sells AI software that automates customer service calls, trained on 300 million calls for clients like the NFL and Under Armour. The 76-person company has raised $29M, including a Series A in early 2026.
The growth story
Flip grew from 27 to 76 employees between 2023 and 2026, raising $29M along the way, most recently a Series A in January 2026.
About
Flip makes voice AI that handles customer support calls for brands. Its system learns from past call data, with clients including retailers and healthcare providers.
The company reached Series A funding in 2026 after seven years in operation. Its engineering team makes up about 15% of staff, with median tenure at two years.
Founders and leadership
Engineering is the largest department with 11 people. Leadership includes investors from Bullpen Capital and Data Point Capital, though specific executive roles aren't detailed.
The Flip org chart
Brian Schiff (Co-Founder, CEO) leads 35 mapped leaders with 11 direct reports. Click +N to expand a team; names link to the person’s public profile.
Departments, and which ones grew
Headcount by function: Engineering 16 (+60% YoY), Sales 12 (+71% YoY), Customer Success and Support 12 (+200% YoY), Product Management 8 (+60% YoY), Business Development 6 (+50% YoY), Marketing 5 (+150% YoY).
Talent flow
Employees frequently come from taxi tech firms like iCabbi and City Taxis, with Amazon as the top destination for departures. Four staff studied at UC Davis, the most of any school.
Most common previous employers of Flip staff: iCabbi (3), Amazon (2), Solv. (2), Salesforce (2), City Taxis (2), Bowdoin College (2). Former Flip employees most often moved to Amazon (4), Taxi Butler (2), Plot (2), Google (2), IntouchCX (1), Nurse Decoded (1).
Alumni worth knowing
The Flip mafia
Five alumni founded companies, most notably RentEngine (14 employees) and Akave (13 employees). Others launched smaller consultancies and blockchain projects.
5Leor Alon, was Founder & Head of Technology until 2017Daniel León, was VP of Operations until 2021Joanne Vega, SHRM-CP, was Head of Talent, West Coast until 2025Christopher Paik, was Business Development Manager until 2025Derek Granito, was Software Engineer until 2017Hiring now
Web traffic
Traffic mix: 30% direct, 40% search, 23% social, 0% paid.
What this company is made of
Most common skills at Flip: Leadership (33), Customer Service (30), Management (24), Sales (22), Communication (21), Python (Programming Language) (20), Marketing (18), Microsoft Office (18).
Where the team actually sits
Flip people are concentrated in New York, United States (20), California, United States (10), Los Angeles Metropolitan Area (6), United States (6). 3 offices on record.
Search footprint
Flip attracts about 186 organic search visits a month, traffic worth roughly $1K a month if bought through ads. It gained 87 ranking keywords and lost 74 in the last period.
What employees say
- Compensation
- 3.00 / 5
- Career opportunities
- 3.10 / 5
- Senior management
- 3.00 / 5
- Work-life balance
- 2.70 / 5
Frequently asked
Flip has 76 employees as of September 2026.
Flip has raised $29M in total, most recently a Series A round in January 2026.
Flip was founded in 2018 by Brian Schiff, Sam Krut.
Brian Schiff (Co-Founder, CEO) sits at the top of Flip's reporting structure, with 11 direct reports.
The most common previous employers of current Flip staff are iCabbi (3 people), Amazon (2 people), Solv. (2 people).
Former Flip employees most often move to Amazon (4), Taxi Butler (2), Plot (2).
At least 5 companies have a founder who previously worked at Flip, including RentEngine, Akave, People Pop Consulting.
Flip attracts about 186 organic search visits a month, worth roughly $1K a month in equivalent ad spend.
The most common skills among Flip staff are Leadership, Customer Service, Management, Sales, Communication.
Flip staff are concentrated in New York, United States (20), California, United States (10), Los Angeles Metropolitan Area (6).
Flip has about 16 people in Engineering, up 60% over the past year, as of September 2026.
Flip has about 12 people in Sales, up 71% over the past year, as of September 2026.
Computed from 63 current and 81 former Flip profiles, as of September 2026. Source: Crustdata.
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