How to Keep Your Team Aligned—Even When the Goalposts Keep Moving
An Interview with Tyler Masterson, Founder and CEO of TrueRoll
Alignment is often misunderstood. It’s not about consensus, feel-good mission statements, or vague aspirations. True alignment is about clarity—clarity of purpose, clarity in how teams collaborate, and clarity in how value is delivered to customers.
In my recent conversation with Tyler Masterson, CEO of TrueRoll, he gave the concept a tangible, practical meaning that resonated deeply. At its core, alignment in a product-centric startup is about defining a clear theory of change: understanding how your product delivers value to customers, ensuring it’s sold in a way that reflects its intended use, and then aligning your team’s efforts to realize this vision—even as the business evolves. You can watch or listen to the full interview here.
For startups like TrueRoll—a company working with more than 80 government offices to improve property tax accuracy, compliance, and revenue—alignment is a critical factor in delivering impact. But it doesn’t happen by accident.
Here’s how Tyler breaks it down.
Defining the Theory of Change: Vision to Customer Value
Tyler’s approach to alignment starts with a fundamental question: What is your product’s theory of change? At TrueRoll, the vision is to help customers achieve more while requiring less effort on their part. “My vision for the product is to deliver value in a way that minimizes effort for the customer,” Tyler explained. “I want them in the tool less, not more.”
This clarity about the company’s value proposition drives everything, from product design to customer engagement. But defining value is just the beginning. Tyler stressed the importance of ensuring that what’s promised during the sales cycle aligns with how the product is intended to be used. “There has to be a clear connection between what is being sold and the outcomes the customer achieves,” he said.
Why is this so hard to get right? Because achieving alignment across the organization requires everyone—from sales to customer success to product development—to play a part in the chain. And in the fast-moving world of startups, the goalposts are constantly shifting as the business learns and grows.
Unpacking Friction: Role Clarity, KPIs, and Incentives
One of the recurring themes in our conversatios how friction arises when alignment breaks down. Tyler shared an example from TrueRoll’s customer success team. “They were using engagement in the tool—like how often customers logged in—as an indicator of health,” Tyler said. “But that metric conflicted with our vision. We want customers to get value while spending less time in the tool.”
This disconnect pointed to deeper issues with role clarity and incentives. “If two people have different definitions of what a customer success manager does, you’ll see friction,” Tyler explained. Similarly, when incentive structures don’t align with the company’s overarching goals, they can inadvertently encourage behaviors that create noise rather than results.
To address these challenges, Tyler emphasized the importance of defining success clearly at every level. “It’s about connecting vision to strategy to execution,” he said. When everyone understands how their role contributes to the company’s broader goals, alignment becomes a natural byproduct.
Maintaining Alignment as the Goalposts Shift
One of the hardest aspects of alignment is maintaining it as the company evolves. “The nature of a startup is to learn and adapt,” Tyler said. “As you learn more, the goalposts move. And getting everyone on board each time is really difficult.”
So how does a company stay aligned through constant change? Transparency is key. At TrueRoll, direct messaging is discouraged in favor of public Slack channels where conversations are visible to all. “This way, everyone can see the conversation evolving,” Tyler explained. “It’s crucial for a living, changing organization.”
This practice fosters accountability and helps the entire team stay informed. But it also requires a high level of trust. “If someone’s off-base, it’s on us as leaders to clarify,” Tyler said. “It’s not their fault—it’s a signal that we haven’t communicated clearly enough.”
Designing a Culture of Alignment
Beyond transparency, Tyler highlighted several other strategies for designing a culture that stays aligned through change:
Better Handoffs: When a customer is sold a deal, everyone—from the sales team to customer success to the decision-maker on the customer’s side—should be in the room. “It’s about ensuring that everyone understands the definition of success and what we’re aiming for,” Tyler said.
Fewer, Clearer Goals: Tyler stressed the importance of narrowing focus. “If you have too many definitions of success, you’re bound to create conflicts,” he said. By identifying the few metrics that matter most, teams can stay aligned and avoid unnecessary friction.
Iterative Goal Setting: Rather than waiting for the perfect goal, start with what you know and iterate. “Set expectations that goals will change as you learn more,” Tyler advised. “This mindset helps teams adapt without losing alignment.”
Tips for Leaders
For leaders tackling inevitable alignment challenges, Tyler’s advice is both simple and profound: Start by being honest with yourself. “What are the biggest challenges in your organization? What are the biggest levers for impact?” he asked.
If you’re struggling to see the full picture, seek external advice. “Sometimes you’re too close to the problem,” Tyler said. “Talking to someone with fresh eyes can bring clarity.”
Our conversation left me reflecting on the immense power of alignment—not just as a business strategy, but as a cultural foundation. Designing a startup culture that stays aligned through constant change is no small feat, but Tyler’s insights offer a practical roadmap. From defining a clear theory of change to fostering transparency and narrowing focus, these strategies can help any organization connect vision to execution.
As Tyler said, “Alignment minimizes friction. It’s what connects vision to execution.” And in a world where startups are constantly evolving, that connection has never been more important.
These practices are at the heart of my Elevated Start-Up Program, which helps leaders connect the dots between their mission, market, and team dynamics to drive sustainable growth. If you’re interested in learning more, visit jessicalynnmacleod.com or drop me a note at jessica@jessicalynnmacleod.com.
If you’re interested in following Tyler’s amazing work at TrueRoll, you can connect with him on LinkedIn.