TITLE: Director of Customer Success
REPORTING TO: Cofounder/CRO
LOCATION: Brooklyn, New York (Onsite M-F)
Who The Flip Is Flip?
Ever call your favorite eCommerce brand or healthcare provider, and have a crazy good Voice AI answer? That’s Flip. Hundreds of brands from Under Armour and Tory Burch in retail to Experity and Fast Pace Health in healthcare trust Flip to have millions of phone calls with their customers every month.
We’ve built our company on the idea that the best way to grow is to have a reference list as long as our customer list, and a constant belief that the team is the best thing we’ve built. Both are true today and increasingly so every day.
Many on our team would tell you this is their favorite place they’ve ever worked, and the hardest they’ve ever worked. It’s ideal for people who want to go all-in, do the work, ride the roller coaster, and have a great Flippin time doing it. We’re a small and mighty team of 50 today with offices in NYC, LA, and the UK.
What You’ll Do
This is a build-and-own role with real stakes. You will step into active, high-impact customer relationships from day one. You’ll work directly with the founders and partner closely with Sales, Product/Engineering, and Marketing.
Own Outcomes for Our Most Strategic Customers:- Make Flip the most impactful tool in our customers’ tech stack by delivering clear business outcomes and ROI
- Ensure our reference list grows as fast as our customer list
- Build trusted, executive-level relationships across stakeholders — becoming our customers’ favorite partner
- Travel frequently to meet customers in person and deepen partnerships
- Partner with Sales to support late-stage evaluations and close complex deals
- Lead onboarding and implementation through the full lifetime of the customer relationship
- Go above and beyond to solve edge cases, test scenarios, and deliver outcomes customers didn’t think were possible
- Master Flip’s platform quickly (eCommerce/Retail or Healthcare)
- Unpack customer problems beyond surface symptoms to uncover root causes
- Translate customer needs into actionable feedback that shapes product strategy and roadmap
- Hire, mentor, and scale a high-performing CS team as the business grows
- Build scalable systems, processes, and operating rhythms without losing quality
- Act as a player-coach who raises the bar for execution, ownership, and culture
Partner Across the Business:
- Collaborate with Product to ship customer-driven improvements
- Work with Marketing to turn customers into advocates and community leaders
- Use data and storytelling to show impact, performance, and ROI
- You have exceptionally high aptitude and work ethic — you move fast and choose to go deep
- You’re the person people want in the room when things get hard
- You bring optimism, grit, and creative persistence when there’s no obvious answer
- You’re craving a real rocketship — and want to help build it, not just ride it
If reading this makes your pulse go up instead of down, you’re probably in the right place.
What You Bring- 10+ years of experience leading Customer Success for a B2B software company
- Proven experience scaling CS from early customers to hundreds of accounts
- A track record managing complex, high-stakes, business-critical relationships — and the ability to articulate exactly how you navigated the hardest moments
- Strong executive communication skills with customers and internal stakeholders
- Deep ownership mentality — you see problems as yours to solve
- Player-coach mindset with a passion for developing exceptional teams
- Obsession with customer experience and delivering outcomes
- Experience building CS processes in both startup and enterprise environments
- Passion for storytelling, references, and customer community building
- Experience at an early-stage Healthtech company (Series A–C)
- Familiarity with EHR/PM integrations (Epic, Athena, Experity, eClinicalWorks, etc.)
- Knowledge of healthcare data standards (HL7, FHIR, HIPAA)
- Understanding of payer/provider dynamics and patient experience workflows
More About Us
- We're international, spanning the US, UK, and Canada
- We’ve raised +$30M to date including our recent $20M Series A - backed by Ridge, Next Coast, ScOp, Bullpen Capital, Data Point and Forum Ventures, as well as founders & executives from Amazon Alexa, Ada, Attentive, and Simon Data
- Comprehensive healthcare and unlimited vacation, including a mandatory half week for everyone over July 4, and a full week off at the end of the year
- In office 5 days/week
#FlippinLegend
Final compensation may vary based on location, experience, and qualifications. This role is also eligible for bonus and/or commission as well as equity, in accordance with company policy, and subject to board approval.
Our customers span the globe, and so do our offices. Flip is committed to providing equal employment opportunities for all employees, applicants, and covered individuals regardless of protected characteristics. We want our company to be as diverse and inclusive as our customers.
What We Do
In a world of products that are AI everything for everyone - all channels, use cases, industries, languages, etc - Flip stands out by doing the single most important thing 10x better for brands in a few very specific verticals. Flip automates millions of phone calls per week for hundreds of retail eCommerce, healthcare, and transportation brands. Our reference list is as long as our customer list. Our team is the best thing we’ve built. To learn more: www.flipcx.com Be a #FlippinLegend
