Meet Ashley Artrip

We’re excited to introduce you to the always interesting and insightful Ashley Artrip. We hope you’ll enjoy our conversation with Ashley below.

Ashley, appreciate you making time for us and sharing your wisdom with the community. So many of us go through similar pain points throughout our journeys and so hearing about how others overcame obstacles can be helpful. One of those struggles is keeping creativity alive despite all the stresses, challenges and problems we might be dealing with. How do you keep your creativity alive?

Creativity, for me, blooms at the crossroads of the unexpected. I find magic in the collision of different worlds—where architecture influences software design, where ancient philosophy reshapes modern leadership, where a morning hike sparks a breakthrough in problem-solving.

My creative practice rests on two pillars: serendipity and structure. While I immerse myself in diverse inspirations—from avant-garde jazz to medieval literature, from urban street art to quantum physics—I’ve learned that creativity also demands discipline. Each day, I carve out sacred spaces for deep work, maintain a digital garden of nascent ideas, and rapidly prototype concepts to separate the promising from the merely interesting.

The most potent fuel for my creative engine comes from intellectual friction. In Reading Rhythms discussions, strategy sessions, or impromptu coffee conversations, I seek out minds that challenge my assumptions. These encounters with fellow explorers—artists, entrepreneurs, scientists, dreamers—often illuminate paths I never knew existed, transforming how I approach both problems and possibilities.

Thanks, so before we move on maybe you can share a bit more about yourself?

I’ve always been drawn to creating spaces—both literal and figurative—where people can connect, grow, and feel a sense of belonging. That passion has shaped my career across multiple ventures, from building Reading Rhythms, a viral reading party movement, to my work as a Go-to-Market (GTM) Engineer at Clay, where I blend sales, automation, and strategy to help companies scale more efficiently.

At Reading Rhythms, we’ve transformed the simple act of reading into a social experience, helping people reconnect with themselves and others through shared quiet time. It’s been incredible to see it grow from a small experiment into an international movement. Right now, we’re expanding to new cities and deepening our membership experience to make it even more impactful.

At Clay, I get to be at the forefront of how sales teams use automation, AI, and data to build better go-to-market motions. It’s exciting to take something as complex as revenue operations and turn it into a system that feels seamless and scalable.

The common thread in everything I do is designing experiences that help people connect—whether it’s through literature, business strategy, or community building. I love pushing the boundaries of what’s possible and can’t wait to see where the next big idea takes me.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

1. Insatiable Curiosity: My mind has always been a restless explorer, driven to understand the intricate machinery of success—from the psychology behind a perfect sales pitch to the invisible threads that weave communities together. This perpetual questioning has shaped not just what I learn, but how I learn. To those beginning their own odyssey: embrace the power of not knowing. Let your questions be bolder than your certainties. Venture beyond the comfortable boundaries of your field, because often the most profound insights hide in unexpected places.

2. Adaptive Resilience: The entrepreneurial path, particularly in building Reading Rhythms, has taught me that rigid plans are often the first casualty of reality. True strength lies not in perfect execution, but in elegant adaptation. When resources were scarce, creativity became our currency. When conventional approaches failed, innovation became our compass. For those navigating their own uncertain waters: embrace the chaos. Let each obstacle become a lesson in resourcefulness. Your ability to pivot with grace and resolve problems creatively will often matter more than your initial strategy.

3. Relationships: Every significant milestone in my journey bears the fingerprints of meaningful relationships. Success isn’t a solo expedition—it’s a collaborative adventure enriched by the wisdom, support, and perspectives of others. The most valuable advice I can offer: cultivate genuine curiosity about people. Master the art of asking questions that unlock stories and insights. Plant seeds of generosity without expecting an immediate harvest. In time, you’ll discover that authentic connections create opportunities that no amount of strategic planning could devise.

These three elements—curiosity that never sleeps, resilience that transforms challenges into opportunities, and connections that run deeper than transactions—have been my compass points in navigating the unpredictable waters of entrepreneurship and innovation. They’re not just strategies; they’re a way of being that opens doors you didn’t even know existed.

How can folks who want to work with you connect?

Yes! I’m always looking to collaborate with thoughtful, innovative people who are passionate about career growth, go-to-market strategy, and the ethical use of AI.

Who I’d Love to Connect With:
• People with compelling career journeys – I host a career podcast where I dive into stories of how people have navigated big career shifts, unexpected pivots, and breaking into new industries.
• GTM leaders & operators – I’m building a newsletter on go-to-market strategy, and I’m looking for experts who are pushing the boundaries of what’s possible in sales, marketing, and revenue operations.
• People excited about ethical AI – I’m fascinated by how AI can be used responsibly in sales, hiring, and decision-making. If you’re working in this space, I’d love to chat.

Contact Info:

• Website: https://engineeringrevenue.beehiiv.com/
• Linkedin: https://www.linkedin.com/in/artripashley/