“If I listened to everything our customer said, our product would be horrible.”
Why do some companies sprint from seed to Series A in 18 months, while others grind for years and never quite get there?
The metrics look similar on paper. Everyone’s got revenue. Everyone’s talking to customers. Everyone’s iterating. But something fundamentally different is happening under the hood.
We brought together three people who see this from every angle to figure it out: Wiley Jones (CEO of Doss, who just raised a Series A 18 months after founding), Rajeev Behera (CEO of Every, 2x founder), and Lexi Burbey (investor at Sound Ventures writing Series A checks across the AI landscape).
What came out was unintuitive: a lot of the conventional wisdom about getting to product-market fit might actually be leading founders in the wrong direction.
What we covered:
- Why revenue milestones don’t mean what they used to (and what signals PMF instead)
- The case for long-term conviction over rapid iteration
- How to identify real customer pain versus nice-to-haves
- What Series A investors actually look for beyond the numbers
- Why your ICP is a moving target, not a fixed definition
This virtual event was presented by Every
Every is the modern back office for startups. We combine powerful software with expert support across payroll, benefits, HR, accounting, and taxes, all in one platform. Founders use Every to save time, stay compliant, and scale faster without the busywork. Whether you’re hiring your first employee or expanding globally, Every makes it easy to grow your team and run your company.
Revenue Quality vs Revenue Numbers
Lexi opened with something critical for this particular moment in the ecosystem:
“We live in an era right now where it’s really easy to conflate the revenue that you’re seeing with product-market fit. Companies can go from 0 to 10 million in 2 years. The quality of that revenue has changed drastically.”
So what actually proves product-market fit today?
Renewal cycles are the real test. “Have you undergone a renewal cycle, or something where your customers have re-engaged, and it is an obvious re-engagement?” Lexi explained. For enterprise customers especially, investors want to see some sort of renewal cycle or evidence that customers have opted up before they write checks.
Second-year retention tells the truth. Rajeev emphasized that first-year numbers can be misleading:
“Most people look at churn and just blend old cohorts—people who are brand new customers and old customers together. If you look at cohort-level churn, the real test is, do they stay the second year? It takes two years to transition off B2B SaaS software in general.”
Market pull beats arbitrary benchmarks. When Doss raised their Series A, Wiley described feeling “a really large shift in market pull”—not just from existing customers, but the ability to sell to larger organizations, charge higher ACVs, bring down implementation time, and bring down sales velocity.
“ACVs expanded by 3X, and then again by 3X, and then again by 3X,” he noted. “Anyone who hears those things is like, I don’t care how much money you’re currently making, let’s go put a lot more dollars to work behind this thing.”
The metrics that matter vary dramatically by company type. As Wiley pointed out:
“Our business doesn’t care about retention. We have no churn. We’re an ERP. We’re not looking at MAUs or DAUs. I’ve never even looked at that.”
Long-Term Conviction and Iteration Theater
Wiley’s approach inverts the lean startup playbook:
“There was this lean startup era where people were like, let’s iterate our way to the right thing. The long-term oriented conviction around what you’re doing and the preciseness of it is criminally underrated. We don’t rework things. We tend to get things right almost on the first try. It means you feel like you’re going slower.”
The key difference: working backwards from a 5-10 year vision and focusing on getting the foundational work right, rather than chasing week-over-week growth metrics.
Rajeev offered a more nuanced take based on stage:
“When you’re a seed stage company and you don’t have product-market fit, you could start creating a long-term vision, but honestly, it doesn’t matter too much. At that point, it is good to churn through things and see if there’s growth, then move on to the right thing. But as soon as product-market fit becomes real, then I slowly start thinking about long-term vision. That’s the flip that makes you a generational company.”
The distinction matters. At his last company, Rajeev explained they got to $20 million ARR by “quickly squeezing and hiring more people and squeezing the revenue.”
“But since we were so focused on squeezing the revenue to hit the VC targets, we didn’t think about the long term as much. At some point, growth will slow if you penetrate your TAM. Then you have to have a plan to expand your TAM and keep expanding it.”
Obsess Over Organizational Pain
When it comes to understanding customers, all three panelists emphasized a critical distinction: organizational pain points create stickiness, while individual nice-to-haves lead you astray.
Wiley was particularly direct about this:
“We’re super obsessed with our customers’ pain. If I go and talk to people and they go, ‘this is amazing, we love Doss, this is so cool,’ and I’m like, yeah, but what hurts inside of the company? And they go, ‘no, no, I think Doss is so cool.’ I’m like, okay, uninteresting, not interested, because you have nothing that you’re willing to drive into your organization, because nothing’s fundamentally broken.”
Getting to the real answer takes specific tactics. Rajeev’s approach:
“The way I get the real answers is after they churn. Why did you churn? Usually people will complain about nice-to-haves, but they won’t churn because you don’t have a nice-to-have. When they do churn, there’s a real reason for the churn. If you interview the wrong way, you start prioritizing all these nice-to-haves that people think they want, and it crushes your roadmap.”
Lexi looks for specific metrics during customer calls:
“We will ask very specifically on time metrics—how long does it take you to do this? What did you do before you used this solution? What were the problems there? What does it look like now?” She also focuses on performance metrics: “What are the KPIs that your team is held against? What’s the thing that ultimately makes them look really good? Often it comes down to the performance of the individual who is your champion, who is your buyer.”
The goal is understanding what creates real value. As Lexi noted, they have a portfolio company where the key metric is mean time to remediation of infrastructure issues.
“If that one metric improves by a tiny percent, that person looks really good, and the organization saves $25 million.”
The Emotional Moat and Customer Relationships
Lexi made a point about defensibility that challenges a lot of product-first thinking:
“The only moat today is emotional. Literally, that’s it. That’s where branding comes in, that’s where the way that you actually approach these customers, the relationships that you have with these customers, and then the care that they can feel in the product—that’s solving that exact pain point.”
This plays out concretely in the Series A diligence process. “The first thing that we’re going to do is call your customers,” Lexi explained.
“Having an understanding of what your customers will say means you have to have a pretty deep relationship with them. I can’t overemphasize enough how much the founder’s relationship with your customers matters.”
The relationship can overcome early product limitations:
“Oftentimes, the why I would renew in early days is not because of the product. It’s because of the service and the people element that that founder has instituted with that customer. Sometimes that is a saving grace for early companies. You can out-compete some of the other players in the market and some of the better metrics in the market if there’s a good story there and your customers speak well on your behalf.”
Wiley reinforced this with a point about brand and delivery:
“Counter-positioning and building a differentiated brand is one of the most enduring moats for software companies. But you do have to deliver on that. If you are selling an adaptive ERP and it’s not adaptive, customers will figure that out immediately. The branding only gets you so far. You have to actually do the thing.”
The Bottom Line
Getting from seed to Series A today is about demonstrating quality through renewal cycles, building from long-term conviction once you find traction, solving organizational pain that creates real stickiness, and building customer relationships that can weather early product challenges.
As Rajeev put it about finding your ICP:
“It’s underrated. It’s nice to be methodical about it and line them up on a piece of paper.”
The same applies to the entire journey to product-market fit—being methodical about the right things matters more than moving fast on the wrong ones.
Want more insights? Watch the full session above to hear the complete discussion on ICP evolution, portfolio construction strategies, what actually happens in Series A diligence, and the specific questions that uncover real customer pain points.
