Flip, an enterprise Voice AI platform focused on retail, e-commerce, healthcare, and transportation, has appointed Amy McDonnell as Chief Customer Officer and Lee Nadler as Chief Marketing Officer as it scales operations following a $20 million Series A round in January 2026.
The leadership additions come amid rising demand for Flip’s platform, which replaces traditional phone systems with conversational AI that autonomously resolves customer service interactions. The company has processed more than 300 million calls across over 250 enterprise customers, automating up to 90% of inbound call volume. Its system integrates with more than 80 platforms, including Shopify, Salesforce, HubSpot, and Zendesk.
Flip has taken an industry-specific approach, focusing deeply on select verticals rather than offering a generalized solution. This strategy has helped the company secure clients such as Under Armour, Tory Burch, Care First Urgent Care, and the NFL.
Amy McDonnell brings 25 years of experience in customer experience and business process outsourcing, with prior leadership roles at companies including TTEC, [24]7.ai, TaskUs, WNS, and Convergys, now part of Concentrix. Most recently, she served as Chief Customer Officer at POSE CX. At Flip, she will lead efforts to expand enterprise growth, scale go-to-market operations, and deepen customer relationships.
Lee Nadler brings more than three decades of marketing experience. He previously joined DoubleClick as an early employee and helped guide the company from startup to IPO and eventual acquisition by Google. He later spent a decade at the BMW Group, where he helped build the MINI brand into a globally recognized name. Nadler also founded Sherpa Marketing and has been recognized by Ad Age and inducted into the American Advertising Hall of Achievement. After serving as a Fractional CMO at Flip for 6 months, he is now joining full-time to lead brand and market expansion.
Following its recent funding round, co-led by Next Coast Ventures and Ridge Ventures, Flip has raised $31 million in total. The company is growing 3x year over year and has reached 8-figure annual recurring revenue. Its platform supports millions of calls per month during high-demand periods, such as peak retail seasons, flu season, and major live events.
Founded in 2018 and headquartered in New York, Flip continues to expand its presence across key industries as it positions Voice AI as a foundational layer in enterprise customer experience.
KEY QUOTES:
“When Sam and I started Flip, we knew that winning in this space would require going deeper than anyone else—into the industries, the workflows, and the moments that matter most to customers. Amy and Lee make that mission unstoppable. Amy has spent her career inside the industries we serve and knows exactly where friction lives and what it takes to earn enterprise trust. Lee has built category-defining brands from the ground up. Together, they’re exactly who you want beside you when you’re building something that’s never existed before.”
Brian Schiff, CEO and Co-founder of Flip
“I met Brian and Sam four years ago and knew instantly that we were aligned on something important—the industry needed a smarter, deeper approach, and Flip was building it. Watching that conviction turn into 300 million calls processed and a growing roster of clients made joining an easy call. My mandate is direct: make Flip the foundational layer for every major enterprise customer relationship. We are scaling our go-to-market team with a singular focus on capturing market share and deepening our roots within the world’s most iconic brands. We are building the capacity to not only meet our customers’ needs today, but to anticipate their scale and growth for years to come. At Flip, your growth is our roadmap.”
Amy McDonnell, Chief Customer Officer of Flip
“When I started working with Flip I saw something rare – founders with a clear vision, a team that believes in what they are building, and clients who are not just satisfied, they are advocates we proudly call Flippin’ Legends. I was at DoubleClick when we transformed digital advertising from an experiment into the way every brand went to market in a few short years. AI is doing the same thing for customer experience right now, at an even faster pace, and Flip is the platform that turns that potential into results for innovative brands. Sherpas don’t just point at the summit, they guide you there every step of the way. In a market moving this rapidly, that is exactly what Flip does for every client we serve.”
Lee Nadler, Chief Marketing Officer of Flip
