Where Do You See Yourself?

Most leaders come to us facing one or more of these challenges. The good news? We've solved them before — and we'll solve them with you.

Firefighting Mode

Your customer success team is stuck in firefighting mode, and it's eroding both your team and your revenue.

Your CS team is exhausted and reactive—and it's dragging you down with them. You're drowning in escalations: internally from team members hitting their limits, externally from frustrated customers who've lost confidence in your front line. Instead of working on the business, you've become the top escalation point. Your best people are burning out or leaving, retention is unpredictable, and expansion is an afterthought. You know you need to transform from reactive to strategic—but you can't redesign the plane while you're flying it solo. Squyres & Company has led this exact transformation and will build the systems, structures, and capabilities that free you up to lead while turning exhausted firefighters into strategic partners.

Leading an Unfamiliar Function

You're responsible for customer success, but you've never actually run a customer success organization.

You're a founder or CxO who owns customer outcomes—but customer success isn't your background. You need to make strategic decisions about an unfamiliar function: hiring, org design, metrics, tool stack, compensation structures. Generic consultants give you frameworks; Squyres & Company is that trusted advisor—one who has actually built what you're trying to build, at the scale you're trying to reach, and who understands the unique pressures of driving customer outcomes while delivering business results.

Feedback Without Action

You're collecting customer feedback everywhere and doing almost nothing with it.

NPS surveys, CSAT scores, support tickets, QBR notes, customer exit interviews—you're swimming in feedback, but no one is actually listening. Product has their roadmap, sales has their targets, CS has their top asks, and customer input rarely translates into organizational action. Then you lose a major customer who tells you: "We've been sharing the same problems with you for 18 months. Nothing changed." You don't have a feedback problem—you have a system problem. Squyres & Company will build the system to synthesize these inputs—turning your feedback channels into the foundation for strategic investments across product, process, engagement model, and talent. That's what a Voice of Customer operating system looks like: organizational accountability that turns customer input into strategic advantage.

Navigating the "And"

You're being pulled in competing directions, and everyone's telling you to pick one.

Cut costs while improving retention. Scale without adding headcount. Drive results while your team is burning out. Improve customer experience while tightening efficiency. Everyone frames it as a trade-off: quality OR efficiency, customer experience OR employee experience. But you don't have the option for either/or—your business needs both. Squyres & Company operates in the productive tension between apparent opposites and will navigate a successful path to both. Because sustainable customer success requires investing in the people delivering it, and the best solutions deliver on multiple dimensions simultaneously.

Unpredictable Revenue

You can't reliably forecast customer retention or expansion, and your board is losing patience.

Every quarter feels like a guessing game. Churn surprises you, expansion opportunities slip through the cracks, and your forecasts are consistently wrong. Worse—it makes you look like you don't know what the hell is going on in your own business. Your board isn't just losing patience; they're losing confidence. Either you lack the early warning systems, health scoring, and data foundations to predict customer revenue—or you have them and they're unreliable. You're making decisions based on stagnant, surface-level details instead of real insight. You need someone who will build the systems, processes, and discipline that transform retention and expansion from guesswork into reliable forecasts.

Sales-CS Misalignment

There's unhealthy friction between your sales and customer success teams, and your customers are getting dropped in the gaps.

Sales blames CS for under-delivering. CS blames sales for overpromising. Customers arrive with expectations you can't meet, and your CS team spends 60% of their time dealing with escalations and stalls in the onboarding process instead of driving value. Your churn isn't a customer success problem—it's a misalignment problem that starts in the sales process. You need someone who will redesign the end-to-end customer experience and align your GTM organization to support it—shared accountability for customer outcomes, not just shared complaints.

Tech Stack Burden

Your tech stack has become a burden instead of an enabler.

Your customer success tech stack is deep—and your team is drowning in it. Context switching kills productivity, data lives in silos, and you're paying for platforms that create busywork instead of insight. On top of that, you know you need to be incorporating AI to build efficiency and free up your talent for the uniquely human work—but layering AI onto broken processes just creates faster chaos. The answer isn't adding more technology; it's redesigning your processes and operations with technology as an enabler tucked into the right places. You need someone who will rationalize your stack, identify where AI actually adds value, and build a system where technology amplifies what humans do best.

Hit a Wall

Your CS function has hit a wall, and you don't know where to start fixing it.

Retention is stuck. NPS is flat. Your team is working hard, but nothing seems to move the needle. You suspect there are gaps in your processes, tool stack, customer journey, or team capabilities—but you lack confidence in determining what's actually broken and what to prioritize. You need a comprehensive assessment from someone who will quickly see the whole system, diagnose the root causes, and build a prioritized roadmap that directly impacts efficiency, customer sentiment, and revenue retention. And fast.

Outgrown Your Org Design

Your customer success organization wasn't designed for where your company actually is today.

You didn't design your customer success organization—you defaulted into it. People are busy, working hard, but the work isn't being done the right way by the right people. Handoffs are unclear, roles have blurred, and everyone is doing a little bit of everything. Adding headcount feels like the answer, but it's not efficient—more people doing broken work just means more broken work at higher cost. What you need isn't more bodies; it's leverage points that unlock efficiency and predictability as you grow without breaking the bank. You need a strategic redesign that matches your current reality—not a one-size-fits-all model, but a context-specific structure where the right people are doing the right work.

Leadership Bench is Thin

Your CS leadership isn't keeping pace with your organization's growth—and it's showing.

Maybe you promoted your best CSM to a leadership role and now they're struggling. Maybe your CS leader grew with the company but is now over their skis as the organization has scaled. Either way, the impact is the same: the team is underperforming, outcomes are slipping, and you're not sure how to close the gap. Here's the thing—you likely have a good person in that role. They've committed to your business, and you want to commit to them by giving them the best possible chance to succeed. Being excellent with customers and leading a customer success organization are completely different skills, and they may have never had the development or support to make that leap. Squyres & Company—as your fractional leader or trusted advisor—will help them maximize their potential and scale with the business.

High-Stakes Transition

You're navigating a high-stakes transition, and failure isn't an option.

Maybe it's a fresh fundraise with a new growth imperative. Maybe the business is declining and you're running out of runway. Maybe it's M&A integration, a new product launch, a pricing model overhaul, or organizational restructuring. Whatever the trigger, you're in a moment where execution is critical and the margin for error is thin. You don't have time for endless strategy cycles or nonstop debate without action. Squyres & Company thrives in transformation—aligning teams, mapping tactics, and delivering results when the path is unclear and the stakes are highest. We stabilize revenue, restore customer confidence, and protect enterprise value during critical transitions.

Working Hard Without Outcomes

There's a lot of activity, but it's not translating into the outcomes you need.

Your team is busy. They're putting in the effort. But you suspect they're working on the wrong things—because all that work isn't moving retention, expansion, or customer satisfaction. You have dashboards full of data that don't tell you what actually matters or what needs to change. The issue isn't effort; it's direction. You need someone who will prioritize the right work with you, design the dashboards with leading and lagging indicators that surface problems early, and create clarity about where to focus so your team's hard work finally drives the outcomes your business needs.

DO ANY OF THESE SOUND FAMILIAR?

You don't have to solve them alone. Reach out below to see how we can help.

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.