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Three Years Selling at Freshpaint
I’ve been at Freshpaint for about three years now, which is long enough to see how things actually play out, not just how they’re pitched during the interview process.
When I joined, the company was much earlier. The product was still taking shape, the market was less defined, and a lot of what we were selling required a heavier lift. Since then, the biggest change has been how clear the problem has become and how much easier it is to have real conversations with buyers.
Healthcare has caught up quickly when it comes to privacy and data. What used to be more of a forward-looking concern is now something most organizations are actively dealing with. By the time we’re in a conversation, there’s usually already alignment internally that this needs to be solved. That alone changes the job in a meaningful way.
At the same time, the product has matured a lot. Early on, there was more explaining, more educating, and more pushing deals forward. Now, it’s much more about helping customers think through how to implement something they already know they need. The conversations are more strategic, and the deals tend to move with more intent.
The sales motion has also become more defined. It’s a true enterprise process. You’re working across multiple stakeholders, balancing different priorities, and building consensus. It’s not high volume and it’s not easy, but if you enjoy running complex deals and seeing them through, it’s a good environment for that.
One thing that has stayed consistent over the three years is how the company operates internally. There’s strong alignment across teams, and sales is not working in isolation. When something comes up in a deal, you can get the right people involved and actually move things forward. That has been true from early on and has only improved as the company has grown.
The other thing you notice over time is that this is not a place where people get carried. The expectations are clear, and people are held to a high standard. At the same time, there’s a lot of support if you’re willing to take ownership and put in the work. The people who do best here are the ones who stay proactive, manage their own pipeline, and don’t wait for things to come to them.
From a timing perspective, it’s been interesting to see the company move from early traction to something much more established. The product works, customers are buying, and there’s real momentum. But the market is still wide open, especially in healthcare where a lot of organizations are just starting to take this seriously.
That creates a good balance for sellers. You’re not trying to prove something from scratch, but you’re also not stepping into a territory that’s already fully built out. There’s still room to create opportunities and build something meaningful.
After three years, that’s probably the simplest way I would describe it. The job has gotten easier in the ways that matter, but it still requires real ownership to be successful.
If you’re looking for something predictable and highly structured, this probably isn’t the right place. If you want to sell into a market that’s becoming more important, work on deals that actually matter, and have room to build something over time, it’s a strong opportunity.
