ABOUT SQUYRES & COMPANY

WE KNOW WHAT IT TAKES BECAUSE WE’VE DONE IT

Squyres & Company was founded on a simple observation: most consultants have never actually led the functions they're advising on. They have frameworks, certifications, and slide decks—but they've never been in the hot seat when retention numbers crater, when your best CSM quits the week before a board meeting, or when you realize your entire customer success organization is built on a foundation of duct tape and hope.

We're different. We've led customer-facing organizations through the exact challenges you're navigating right now.

The Experience Behind the Guidance

MEET DEBRA SQUYRES

Founder of Squyres & Company, Debra brings over 30 years of executive leadership experience, including a decade in human resources and 20+ years in customer success, operations, and customer experience — spanning high-growth startups to public companies navigating IPO transitions. This combination of people operations and customer-facing leadership gives her a unique perspective on building organizations where both customers and teams thrive.

Her track record includes:

  • Scaling customer success organizations and driving revenue growth as high as 35x

  • Leading teams of 450+ customer experience professionals

  • Consistently achieving 90%+ retention and expansion models that drive net customer growth across multiple companies

  • Delivering measurable impact: 21% NPS increases, 50% customer experience improvements, >20% team productivity gains

  • Building customer feedback loops that confidently inform strategic investments in product, process, customer engagement models, and talent

  • Leading M&A integration and due diligence for customer-facing functions

  • Building customer success capabilities from the ground up—and rebuilding them when companies have outgrown them or they've broken

Most importantly: Debra has lived every problem listed on this site. She's been the executive firefighting escalations at 11 PM. She's rebuilt dysfunctional sales-to-CS handoffs. She's designed org structures for companies that outgrew their original models. She's sat across from boards explaining why retention forecasts missed—and then fixed the underlying systems to make forecasts reliable.

WHY SQUYRES & COMPANY EXISTS

Too many leaders are stuck in impossible positions: responsible for customer outcomes in functions they've never run, with teams that are overworked and underequipped, in organizations that treat customer success as a cost center instead of a revenue engine.

And here's what typically happens: Companies hit a funding milestone or reach a certain size and decide they need a VP or C-level hire. But that decision puts enormous weight and pressure on the business—it's expensive, it takes months to find the right person, and if you get it wrong, the cost is devastating. What these companies actually need isn't necessarily a big title—it's experience. Someone who can see around corners, separate signal from noise, and navigate effectively when the stakes are highest.

That's why Squyres & Company exists. We provide seasoned executive expertise at the right time, in the right way, without the long-term salary overhead of a permanent hire. We build momentum while helping you determine what you actually need long-term—and if hiring an executive is the answer, we ensure you make the right kind of hire. Because what companies need varies dramatically by stage and challenge, and the smartest leaders recognize that partnering with experienced practitioners at critical inflection points accelerates outcomes while building lasting capability on their teams.

That's what Squyres & Company delivers: proven frameworks born from real execution, battle-tested experience from leading through growth and crisis, and hands-on partnership that solves today's problems while building tomorrow's capabilities.

OUR PHILOSOPHY

We believe sustainable growth doesn't come from doing more—it comes from doing the right things well.

We believe most business challenges extend well beyond any single function, which is why our approach addresses the entire system: strategy, operations, people, and process.

We believe the best solutions deliver on multiple dimensions simultaneously—you shouldn't have to choose between quality and efficiency, between customer experience and employee experience, between growth and sustainability.

We believe in building high-performing teams, not creating dependency. Our goal is to make ourselves obsolete by elevating the capabilities of the people around you.

And we believe that when failure is not an option and time is of the essence, you need a partner who has been there, done that, and knows how to deliver.

Ready to tackle what’s holding your team back? Reach out below.

Get in Touch

This conversation is most valuable for:

  • CxOs and founders responsible for customer outcomes

  • CS leaders navigating organizational challenges

  • Companies in transition (fundraising, M&A, restructuring)

  • Leaders who need proven expertise, not generic consulting

If you're serious about building sustainable growth and you recognize your challenges in our Problems We Solve page, let's talk.