Growth Is a Team Sport: How Checksum Tackles Growth

Growth Is a Team Sport: How Checksum Tackles Growth 

super{set} Company Building Spotlight: Abigail Aragon, Founding GTM and Maysam Sadeghi, Head of Forward-Deployed Engineering

At Checksum, growth has been fast, market-driven, and executed under pressure. But what’s made the difference is how tightly the team members closest to customers stay aligned as everything accelerates.

Inside super{set}’s portfolio, we see these inflection points and it’s always insightful to learn how teams manage through this and stay focused on the most important outcomes. Growth shows up quietly during handoffs between sales and customer engineering. Opportunities arise in the space between what was promised and what gets delivered. Startups that handle these moments well don’t just move fast. It also requires open, honest conversations that align everyone,  while executing at speed.

In this conversation, Abigail and Maysam talk candidly about what it’s been like building through rapid growth without losing signal, why some things shouldn’t be automated yet, and how learning loops are critical when the pace is relentless.

Let’s take a look at Checksum’s growth from the inside-out. 

Q: As Checksum’s growth accelerated, what was the first thing that felt fragile and what did you do to strengthen it before it broke?

Abigail: Honestly, everything felt fragile.

We were coming into a company growing at high velocity. We had a lot of inbound interest and more customer-facing calls than Gal (founder) and I could handle. So the first thing we did was implement a process, just enough structure so that when things seemed fragile, we could actually see where they were breaking and course-correct quickly.

We used to joke that we were the control group. The things we did in 2025 really set the stage for how the company scaled from a go-to-market (GTM) perspective. That awareness shaped a lot of early decisions.

Q: From your seats, where does scale show up most viscerally day to day - a place you feel the pressure before you see it in metrics? 

Maysam: We move very fast. Our product is iterating constantly. Engineering velocity is very high. We’re tuning models continuously based on customer feedback. 

At that speed, you sometimes break things. And I can usually feel it before it shows up in metrics. I’ll notice something small, and I know that in two or three days, if we don’t address it, it could become a major bottleneck or negatively impact customers. What’s helped is that we’ve built processes with the engineering team so we can catch and fix those stress points before customers experience them.

Customer Engineering is actually a huge part of the product motion so we even write PRDs sometimes. We’re the first users of the product. This tight collaboration lets us move fast and see where customers will be six months down the line and so we can prepare for it.

Q: Walk us through a real customer journey from a deal close to the customer going live. Where does alignment truly happen, and where does it still require deliberate effort or trust?

Abigail: I’ll start with the second part because Maysam and I were literally talking about this.

We were aligning on a customer who’s launching an evaluation. We talked through both short-term and long-term goals and made sure we were personally aligned on how we’re going to deliver value, not just during the evaluation, but throughout the entire customer relationship.

That’s critical. Once a customer signs, it’s a covenant. It’s not just paperwork. It’s a commitment. So sticking to the landing after the deal closes is really important.

The alignment starts on the very first customer call. As momentum grows, we loop in more people. We do demos. Customers meet Maysam and the Customer Engineering team. We write out very detailed deliverables for the evaluation period.

We think of it as a triangle of alignment: Sales, Customer Engineering, and of course, the customer. The POV success really hinges on that triangle holding.

Q: What’s the most common way your functions unintentionally create pain for each other and how have you learned to catch that earlier without slowing momentum? 

Maysam: We’re a small, humble, but mighty team, and we move fast. Sometimes Sales commits to something that requires more effort than expected. Sometimes product changes negatively impact the customer workflows. None of it is malicious even as it impacts Customer Engineering’s day-to-day. What’s worked well is we communicate constantly. If Sales sees a need, we align with Product and Customer Engineering immediately to plan delivery. Communication is the glue.

Abigail: I’ll say the quiet part out loud, sales can sometimes overpromise. It’s not intentional. We hear a use case and say, “Yeah, we can do that,” without fully understanding a customer’s environment.

That can create a lot of work for other teams. What’s helped is that everyone has a strong, positive, can-do attitude. Through our shared mindset of customer value first and our can-do attitude, we deal with issues as they come up instead of letting them fester.

Q: As volume increases, what’s something you’ve intentionally not automated or rushed because judgment, context, or human care still matters  even when speed is tempting?

Abigail: Even though we’re an AI-native company, and we use a lot of AI tools, internally and customer-facing, we choose to slow down intentionally, where human judgment matters. One example is evaluations. We use a human-in-the-loop approach. Our models are good enough to be fully autonomous, but we want human-to-human interaction when we’re talking about test cases, workflows and integrations.

We meet with customers every other week. That high-touch motion is a core part of our success.

Maysam: Even though we can run agents to detect, generate, and heal tests automatically, we intentionally keep forward deployed engineers in the loop.

They know the customer’s pain points, the flakiness of their ecosystem, and they provide daily feedback to the models to make them better. I do see a future where AI does more autonomously, but I always see someone at Checksum monitoring progress for every customer. That’s intentional.

Q: When deals are hot or timelines are tight, how do you make sure customer truth doesn’t get softened, rounded, or lost as it moves through the system?

Maysam: It comes down to people, product, and process. All three are evolving together.

We’ve expanded the team globally, so we have 24-hour coverage across regions. We’re always available to customers. On the product side, we’re the first users. On the process side, everything is iterated collaboratively so we can see bottlenecks ahead of time.

That’s how we stay honest with ourselves and with customers as we scale.

Q: When something breaks at scale, how do you decide who owns the fix and how do you keep that moment focused on learning and momentum rather than blame?

Abigail: We stress “default to action.” It’s less about ownership and more about identifying the problem and fixing it collaboratively.

Sometimes it’s a simple quick fix. Sometimes it’s cross-functional. If a customer doesn’t convert after an evaluation, we write an after-action report where our focus is to learn from the experience and not to assign blame. We know that we’re not going to close every deal and that’s fine as long as we’re learning.

Q: Tell us about a moment where the “right” decision was harder than the “fast” one. What made it uncomfortable, and what changed afterward because you chose it anyway?

Maysam: A customer asked why we couldn’t file bugs directly into their Jira instead of Slack and our dashboard. We didn’t have that feature yet. The fast answer would’ve been no. The right answer is always yes.

So, at first, we manually integrated with their Jira for a while. It was painful. But we used that experience to build the feature properly. Now it’s fully integrated across customers and tools like Jira, Linear, and ClickUp. That decision was uncomfortable, but it shaped the product in a big way for everyone.

Q: How do you create real learning loops between GTM and CX, not just retros, but changes that actually stick while you’re still moving fast?

Abigail: We’re still doing things that don’t scale. GTM shows up on customer calls. Customer Engineering shows up on pre-evaluation calls. We all hear the same things from customers in real time. Maybe that changes later. But right now it’s super productive. Learning firsthand beats listening to recordings later.

Q: What’s something each of you used to believe about growth or scaling that experience at Checksum has fundamentally changed?

Maysam: In past roles, customer pain points were fairly static. Here, customer needs change incredibly fast because we’re at the edge of AI.

And because we’re AI-first, we see problems six to nine months before the market. We see the problems coming and build ahead of them.  That speed is unlike anything I’ve experienced.

Abigail: Same for me. The questions customers ask today aren’t the ones they asked earlier this year. We’ve rebuilt our value proposition multiple times, both strategically and reactively because the market is moving that fast.

It’s exhausting and exhilarating. You have to be adaptable. I feel like I get to bring my whole brain to work every day.

Q: When collaboration is working at its best, what does it look like in the middle of a normal week?

Maysam: When things are clicking, customers are happy. Decisions are made in context. Delivery is smooth. There’s space to think ahead. Most days, that’s the norm.

Q: If someone joined Checksum tomorrow, what’s one behavior they’d notice quickly that tells them, “this is how things really work here” especially when things are moving fast?

Abigail: Day one, Gal said, “Join this call. Read this email. Tell me what you think.” No ramp. No script. No guardrails. It was both nerve-wracking and empowering. But it told me how things really work here and my point of view really matters.

Q: If you were to finish this sentence - “Building Checksum has taught me that…” - what would you say?

Maysam: Staying on top of AI innovation isn’t optional. It’s mandatory for everyone - GTM, product, customer engineering. We have a rule: try AI first on every task. That mindset has driven efficiency across the team.

Abigail: It’s taught me that AI can help customers solve problems they thought were nearly impossible to solve. And it feels really good to help teams regain confidence in velocity and quality.

Closing

At super{set}, we believe growth doesn’t come from speed alone. It comes from teams that stay aligned under pressure, learn in real time, and refuse to let customers become abstractions.

What stands out at Checksum is how deliberately GTM and Customer Engineering stay aligned while moving fast and prioritizing customers first. It’s the  relentlessness of learning and collaboration, plus brutal honesty working together as the company scales.

That’s not accidental. It’s company-building. Checksum’s story is a reminder that growth is, and always will be, a team sport.