Kareem’s Journey with Clay: Lessons in Creative Resistance and Growth

Rebel with a cause: How Clay is rewriting the startup playbook

The path to product-market fit is an unpredictable and often winding journey, and Kareem Amin, co-founder and CEO of Clay, has navigated it with determination, adaptability, and a touch of creative rebellion. From abstract beginnings to achieving exponential growth, there have been several pivotal moments and bold decisions that have shaped Clay’s seven-year “overnight” success story. The latest? A $40M fundraising round at a $1.25B valuation. 

In an unfiltered fireside chat with Rippling’s COO Matt MacInnis, hear how Kareem resisted market pressures to conform, embraced unconventional feedback systems, and redefined what it means to build a product in a crowded space—all to achieve exponential growth with Clay.

There’s plenty of tactical goodies inside the talk, but in case you’re not sold, here is a taste of the lessons Kareem learned “from the startup trenches” that are sure to resonate with any entrepreneur building on the ground today: 

Align business with your passions

Kareem emphasizes the importance of aligning your business with your passions rather than just chasing what seems like a good opportunity. “We need to connect the product to what we are interested in and not just opportunistically what is a good business,” he says.

He shared how this philosophy shaped Clay’s decision to become a product-led growth (PLG) business. “It was substantially more difficult than I thought, but we kept asking ourselves—do we want to sell this way? If we get customers, will we learn more?” By staying true to their interests, Kareem and his team built a business they truly enjoy leading, even through the challenges.

Build quick feedback loops

Kareem advises founders to integrate customer feedback into product development as directly and transparently as possible. “When engineers see the problem and solve it quickly, it motivates them and creates a fast loop,” he says. 

This approach can accelerate product improvement while fostering stronger collaboration and morale within the team.

Momentum is everything

Kareem likens his role to being a “momentum detective.” Once Clay found traction, maintaining that momentum became his top priority. “If you lose it for a minute, it can be ten times harder to get it back,” he says. 

He advises founders to identify areas where progress slows and address them immediately, as sustained momentum is critical for growth and resilience.

Leverage creative resistance

While market feedback is invaluable, Kareem believes founders shouldn’t shy away from resisting conventional wisdom when it doesn’t align with their vision. “Resisting being just a lead-gen tool helped us discover something bigger,” he says. 

Creative resistance, when balanced with market needs, can uncover innovative opportunities and allow startups to carve out unique niches in competitive landscapes.

Trust yourself

“When you make decisions you don’t believe in, you learn nothing when they fail,” Kareem says. Trusting your intuition, even when it’s unconventional, is key to meaningful growth.

He believes founders must back their instincts, even in the face of external pressure, as authentic decision-making aligns with personal values and also strengthens long-term vision.

Operate from wholeness, not from lack of

As a second-time founder, Kareem’s mindset shift before heading into Clay redefined how he approaches the founder gig. “Entrepreneurship is going from one crisis to the next. You need to enjoy the crises and treat them like a game,” he says.

Reflecting further, Kareem says, “I’m not building to prove anything. I’m building from a place of wholeness. Success or failure doesn’t define me.” He emphasized the importance of maintaining steadiness in the face of challenges. “You have to approach it from a place of being steady; otherwise, it wears you down. You have to actually kind of enjoy it.”

This perspective has allowed Kareem to view even the most difficult moments as opportunities for learning and growth, rather than sources of frustration or burnout.

Rippling became an essential part of Clay’s growth story, helping the company scale without losing focus on what mattered most—its mission. For a fast-paced company like Clay, managing critical operations efficiently was non-negotiable, and Rippling provided the tools to keep everything running smoothly.

Hear about his company’s turning points, his advice for entrepreneurs, and how tools like Rippling have helped Clay scale while staying true to its mission.