From the Founder | The Human Side of Voice AI: How Flip is Building a Culture-First Company in the Customer Service Revolution

Why Work Here is a series in which Amit Matani, CEO of Wellfound, has honest, behind-the-scenes conversations with founders, executives, and employees about why their companies are worth joining.

We've all experienced the frustration of calling customer service only to be greeted by an archaic robot asking us to press buttons and navigate confusing menus. As Brian Schiff puts it, many of us think, "How is it 2025, and this is so bad?" It's this universally relatable pain point that Flip is tackling head-on, replacing outdated customer service bots with sophisticated voice AI technology that solves problems for callers.
Beyond innovative technology, Flip stands out in its leadership's unexpected revelation about what truly matters in building a successful company. For Schiff, the journey has led to one critical insight: culture isn't just corporate jargon – it's the foundation of sustainable growth.

🎥 Watch the full interview on YouTube | Listen on Spotify.

From Campus Ride-Sharing to Voice AI: The Evolution of Flip

Flip's origin story begins with a classic college entrepreneurial venture. Schiff and his co-founder met as undergraduates and initially built an Uber-like service for their campus when ride-sharing services weren't yet legal in upstate New York. They expanded to multiple schools before noticing an opportunity in the emerging voice technology space.

"Alexa was starting to come of age and voice tech was having sort of its first moment, or at least its moment before the ChatGPT moment," Schiff recalls. "We were like, 'Hey, this tech's not perfect, but it's way better than those robots you get when you call.'"

They tested their concept in the taxi and ground transportation industry, automating customer service calls. The idea proved successful, and by 2022, Flip raised $10 million to expand into retail and e-commerce. Today, they automate millions of calls weekly for businesses across several industries.

The Perfect Timing of the AI Revolution

While Flip had been working on voice AI technology for years, the recent explosion of generative AI and large language models created the perfect tailwind for their business. According to Schiff, startup success requires "an abundance of both," skill and luck, and Flip's biggest stroke of luck was "being in the right moment at the right time when LLMs came into existence and commercial readiness."

This timing proved beneficial in two crucial ways:

1. Technical capabilities: The quality, speed, and cost-effectiveness of modern AI have enabled Flip to create better products at scale.

2. Market readiness: "When we started doing this five years ago, the idea that AI was going to automate most of your support calls was controversial," Schiff explains. "Everything that's happened with AI in the last 24 months has just done an amazing amount of marketing for us."

Beyond the AI: The Magic of Solving Real Problems

While many companies focus on the AI layer alone, Flip differentiates itself through a three-part solution:

1. AI understanding layer: The foundation that allows the system to comprehend human speech and requests.

2. Workflows: The specific processes that determine how to handle each customer request based on a company's policies.

3. Integrations: Connections to the systems that actually execute actions (like canceling orders or processing returns).

"The magic is in: can you actually solve the problems that people are calling for," Schiff emphasizes. By focusing on specific verticals like retail, e-commerce, and transportation, Flip can build deeper integrations with industry-specific systems, making their solution more effective than a one-size-fits-all approach.

Culture as the North Star: The Flip Hiring Philosophy

Perhaps the most surprising aspect of Flip's approach is how centered it is on people and culture. After experiencing significant turnover with their first 20 hires, Schiff had a revelation about what truly drives company success.

"Every role requires a skill set and culture fit. I think skill set ... has to be there. Really, 95% of what we're recruiting for is culture fit," he explains.

What does that culture fit look like at Flip?

They're searching for people who are:

• "Sick of having four walls and a ceiling surrounding them"
• Eager to build something meaningful
• Frustrated with environments where "nothing is happening"
• Driven to make an impact and move quickly
• Possessing a "burning fire and energy"

This focus on culture wasn't always a priority. Schiff candidly admits,

"Culture... we thought that was corporate hoo-ha... values on the wall in the Sweet Green when you're getting your salad kind of thing. And it unfortunately took 20 swing and misses for us to be like, 'Hey, we need to get real about the importance of the people we have doing the work.'"

The Balancing Act of Startup Growth

Schiff highlights a fundamental challenge for companies in the scale-up phase:

"The hardest thing is winning short-term and long-term. If you only had to play one of the games... decision making would be a lot easier, but that's not the rules of the game."

This balancing act requires a special kind of team member who can:

1. Think both tactically and strategically: Understanding what needs to happen now versus what builds toward the future.
2. Act without permission: "See something, fix it, make it better" without waiting for formal processes.
3. Care broadly: Salespeople who care about the product and engineers who care about the customer.

Finding the Right Fit Through Authentic Conversations

Rather than tricky interview questions or technical assessments, Flip's interview process focuses on three simple questions:

1. "Tell me the story of how you got to where you are."
2. "Tell me what you're looking for in a next opportunity."
3. "Where do you see yourself in a decade?"

Through these open-ended questions, Schiff and his team listen for indicators of care, depth of understanding, and alignment with Flip's environment. They also practice radical transparency about the role's exciting and challenging aspects.

"We are abundantly transparent about what working at this company at this stage of the journey is and isn't in the interview process," Schiff says. "When you share some dirty laundry and some non-glamorous parts of the job and they get more excited, that's usually a good indicator that it's gonna be a good fit."

The Calendar Test: Where Time Goes, Values Follow

When asked about practical changes Flip made to improve their culture and hiring, Schiff avoided suggesting any single "hack." Instead, he offered a more fundamental insight:

"You know what somebody cares about based on what they spend their time thinking about and what they spend their time doing... It's putting your calendar where your mouth is and putting your brain cycles where your mouth is."

This philosophy suggests that building a great team and culture isn't about implementing specific tactics but rather about dedicating genuine attention and energy to these areas—treating team-building with the same seriousness as product development and sales.

Lessons for Founders, Recruiters, and Job Seekers

For Founders:

• Culture isn't fluff: It's the fundamental building block determining your company's ability to execute, especially as you scale.
• Hire for culture fit: Technical skills are necessary but insufficient; the right mindset and energy drive results.
• Put your time where your values are: What you spend time on reveals what you truly value.

For Recruiters:

• Look beyond resumes: Listen to how candidates discuss their past experiences and future aspirations.
• Test excitement against reality: Share challenges along with opportunities to see if enthusiasm increases or wanes.
• Recognize the matching game: It's not about finding the "best" candidate but the right fit for your specific environment.

For Job Seekers:

• Find your right environment: Some people thrive in established structures while others need the dynamism of a startup.
• Demonstrate genuine care: Show how you think beyond your specific role to the broader customer and company needs.
• Embrace transparency: Respond authentically to both exciting and challenging aspects of potential roles.

Looking Forward

As voice AI continues to evolve and customer expectations shift, companies like Flip are positioned at the intersection of technological innovation and human experience. Their journey highlights that success ultimately depends on the people driving the mission forward even in the most cutting-edge technical fields.

For those interested in joining this revolution, Flip (currently 40 people with offices in New York, LA, and the UK) continues to grow rapidly. According to Schiff, the company doubled in size last year and expects continued growth in 2025.

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