Paul
Holder

The Story So Far

Selling a customer onboarding tool is a strange way to spend a career, unless you've had the job.

Paul Holder runs OnRamp, a Boston software company that automates the awkward middle of a B2B sale, the part after the contract is signed and before the customer is actually using the product. This is the part nobody puts on a keynote slide. It is also the part that decides whether a SaaS company makes money. Holder has decided it is a category.

OnRamp closed a $15M Series A in November 2025, led by Koch Disruptive Technologies. The round brings the company's total funding to roughly $29.2M. Headcount is above sixty. Customers are around a hundred. In 2025 the company nearly doubled its team and took a new office in Fort Point, which is the Boston neighborhood where a founder currently signals that they intend to hire aggressively for the next two years.

Holder's path to running an onboarding company is legible in the way that founder paths usually are only in retrospect. Finance degree from Boston College. A stint in strategy consulting. He met his co-founder, Ross Lerner, at HighTower. Then he went to Troops, a Salesforce-adjacent SaaS startup, where he was employee-level customer success lead and then director. Salesforce eventually acquired Troops. Before that, he had run customer onboarding at VTS, the commercial real estate software company. The pattern here is that Holder has spent most of his professional life doing the thing his company now sells software for. When he talks about it in interviews he sounds like a man who has been through the specific pain of a customer going dark two weeks after signing.

The origin story is delightfully cheap. In 2019, Holder and Lerner started interviewing customer success leaders about the onboarding problem, and kept interviewing for three or four months before writing any code. Neither of them could code. When they finally did build something, they built it in Bubble, a no-code platform that lets non-engineers assemble web apps by dragging boxes around. The MVP, by Holder's own telling, was not good. They landed fifteen paying customers on it anyway. Only then did they hire an engineer.

There is a lesson in there that founders skip. Holder does not skip it. He tells the story with a small amount of relish, because it works as a talking point and because it also happens to be what actually happened.

The Wedge

Onboarding is boring, which is the whole point.

The customer onboarding market is not a category you'd invent if you were pitching a VC in a bar. It sits next to customer success, which sits next to CRM, which sits next to the entire post-sale motion of B2B software. It is a wedge. It has budgets. Nobody owns it cleanly, which is exactly why OnRamp exists. Holder's pitch, distilled, is that the messy handoff from the salesperson who closed the deal to the CSM who has to make the customer happy is where SaaS companies lose the most money. He is not wrong.

OnRamp's product does the things you would expect it to do: reusable onboarding templates, guided workflows, task automation, project management, inline communication with the customer, a customer portal, sales-to-CS handoff automation, and integrations with the usual CRMs. Custom branding. Progress tracking. It looks like a category-defining tool in a category that was, until recently, defined mostly by Google Sheets and slack channels named onboarding-acme-corp.

The go-to-market has been more interesting than the product. Holder has talked publicly about replacing cold email with what he calls a LinkedIn "bear hug" outbound strategy, which is what founders call a thing when they don't want to explain the thing but they do want to signal that it worked. It worked. OnRamp scaled to seven-figure ARR and then moved upmarket, on the theory that a 5-to-10 percent onboarding efficiency gain at enterprise scale is worth millions to the customer, and therefore worth a lot to OnRamp.

The Founder

He does the hardest thing first thing in the morning.

Holder is, by his own description, a deliberate operator. He does the hardest work of the day first, before the calendar catches up with him. He values what he calls "truth-seeking," which in his usage means asking the questions people would rather you didn't ask, of customers and employees and yourself. He is comfortable being uncomfortable, or at least says he is, which for a founder is the same thing.

The fun part of the OnRamp founding story, the part that turns up in every podcast, is that both co-founders happen to be twins. Not each other's twin; each of them has a twin sibling. This is a coincidence that means nothing except that it comes up naturally in a conversation, which is the highest and best use of a coincidence. Ross Lerner used OnRamp as a project for a PM101 class in business school, which is another one of those details that would look invented if it weren't true.

Holder is married with two young children, a two-year-old son and a daughter who was three months old at the time of a recent interview. He talks about being present for his family in the same measured tone he uses to talk about picking market lanes. He is, evidently, an enthusiast for consumer electronics and smart home gear, which is the kind of hobby a customer onboarding CEO would have.

The Playbook

Boston, quietly.

The Boston SaaS scene is having a quiet decade. HubSpot is still there. Wistia is still there. Klaviyo went public. OnRamp is one of the newer companies making the case that you can build enterprise software in Boston without needing to relocate anyone, and Fort Point is currently the neighborhood where that argument is being made loudest. Holder is a member of the Forbes Business Council, which is a thing founders do when they have hit a certain size, and he writes and speaks with the fluency of a founder who has done exactly enough podcast episodes to have the answers ready.

The interesting question for OnRamp, and by extension for Holder, is whether customer onboarding stays a wedge or becomes a category. The Series A investors are betting on category. The competitive landscape includes CS platforms, CRMs, project management tools, and roughly two dozen internal Notion pages at every mid-sized SaaS company in the country. OnRamp's argument is that the internal Notion pages are the addressable market. Holder's argument is that he has been the person maintaining that Notion page and he is not going back.

The last thing worth noting is that Holder took his time. OnRamp is six years old at the time of its Series A. That is neither fast nor slow. It is the pace of a founder who was willing to spend three months interviewing customers before writing code, who was willing to build the first version in Bubble and land fifteen customers on a rough MVP, and who is now willing to move upmarket into a slower, larger, more procurement-heavy segment because that is where the money is. It is a very Boston sort of career.