The first ten customers of a software company usually arrive carrying a great deal of symbolic luggage. They are evidence that the idea has escaped the founder’s head. They are names for a presentation. They may even pay. Bryan Stevenson gave Reprise’s first ten another responsibility: help the company work out what it ought to become.
He described them as launch partners. The arrangement allowed for experiments, frank feedback and the possibility that some would leave while the team found its direction. For someone starting a company, that is an unusually useful permission to grant. A customer’s departure can contain information. It need not become a referendum on the founder’s worth.
Stevenson had already been a founder and a technology executive. At Reprise, he was pursuing a problem with an almost comic imbalance: companies could build complicated software, yet showing that software to a prospective customer could require another complicated production. Somewhere between the product and the sales call, the simplicity had gone missing.
Reprise’s first customers helped the founders learn how the product would be used.
A call with some history behind it
The idea reached Evan Powell through a familiar voice. Stevenson had been talking with Sam Clemens, and he contacted Powell to discuss what would become Reprise. These were people whose professional lives had already crossed at InsightSquared. The introduction did not require the ceremonial exchange of biographies that can consume half a first meeting.
Powell recognized the attraction. He had worked in sales and understood the trouble involved in getting a demonstration ready. Still, he wanted to speak with people in marketing and sales before making a commitment. He imagined exploring the opportunity over the next six months.
Three weeks later, he called Stevenson back, ready to proceed. The conversations had produced a repeated request for the product to be built. That is Powell’s recollection of the decision, and it gives the founding story a welcome texture: somebody had an idea, somebody else checked whether people wanted it, and the calendar became considerably shorter.
Prior working relationships can make this kind of exchange easier. There is less time spent establishing whether the other person understands the vocabulary. There is more room to argue about the actual work. Reprise’s beginning brought a technical problem and a commercial problem into the same conversation.
The engineer on the other end
Stevenson’s earlier roles help explain why that conversation was possible. He co-founded InsightSquared and served as its chief technology officer. Clemens was a fellow founder; Fred Shilmover was another. The business worked in analytics for companies trying to understand their performance.
Then came Catalant Technologies. In February 2017, his appointment as chief information officer was reported in Boston. The move placed another technology leadership role between his InsightSquared years and the company he would help start in 2020.
The sequence matters more than a collection of titles. A CTO’s work brings the construction of software into view. A CIO’s role brings another set of organizational demands. A subsequent startup gives those experiences somewhere to meet. Reprise’s proposition would sit precisely at a boundary between the people building a product and the people trying to explain it.
A demonstration is a peculiar artifact. It must resemble the real product closely enough to be convincing, while being manageable enough for a conversation. It needs useful examples. It needs an intelligible route. It must make room for a buyer’s question without allowing the meeting to dissolve into a search for the correct account.
The sales call has a backstage
In a joint interview in April 2022, Stevenson described the fragility of demo environments. Errors could appear during a live sales call. Even when engineering time was available, a new prospect’s demonstration might be built on the remains of an earlier one. Customization could accumulate into a mess.
His concern was concrete. Software with substantial integration requirements is difficult to hand over casually for a first look. Reprise sought to let those companies put a usable product experience earlier in the buying process. Business teams could capture a version, change its contents and show it without asking an engineer to prepare every alteration.
The appeal is easy to understand from either side of the office. A salesperson wants the example to fit the conversation. An engineer wants an afternoon in which every apparently small request does not become another interruption. Each has a reasonable objective. A tool that reduces the collision has somewhere useful to stand.
This is also what makes the idea more interesting than a prettier presentation. The demonstration has work behind it: preparation, maintenance, corrections and repetition. Reprise made that work the subject of a product. The minutes before a meeting can be a surprisingly crowded place.
“Paint a picture of the world you anticipate building.”
Bryan Stevenson, 2021
Then the numbers arrived
In February 2021, Reprise announced a $17 million Series A led by Bain Capital Ventures, with Glasswing Ventures and Accomplice participating. Stevenson was co-founder and co-CEO. The company named Pendo, Gainsight and Medallia among its early customers.
The customer accounts supplied useful detail. Gainsight wanted greater control over what a prospective buyer saw on a first call. Medallia wanted to bring a client’s vocabulary and workflow into the demonstration sooner. These are specific presentation problems. A broad product needs a narrow enough entrance for somebody to understand why it belongs in their day.
By November, a $62 million Series B led by ICONIQ Growth brought announced funding to $82 million. Existing investors joined the round. Trevor Noah and Jeffrey Katzenberg’s WndrCo also participated, adding an unexpected pair of entertainment connections to an enterprise software financing announcement.
Round sizes shown on the same scale. Capital raised by the company.
The funding was intended to expand the customer base and deepen the enterprise platform. The larger the customer, the more consequential the ordinary demands become. A demonstration has to be ready for the next person as well as the first person. Editing it should not create an entirely new maintenance problem.
A financing figure describes resources available at a moment in time. It leaves the daily questions intact. What should the team build next? Which customer request reveals a broader need? How much can be changed before the useful simplicity disappears? A larger budget gives those questions a larger setting.
A demo for the meeting after the meeting
Reprise’s early product expansion addressed two different situations. A salesperson needed something to operate during a live call. A prospective customer also needed something to share after the call, when the seller was absent and somebody else was asking questions.
The company added a Live Demo product to its suite. Stevenson described the aim as helping teams build a reliable experience around their talk track. Sam Clemens framed the two needs together: demonstrating live and giving a prospect a demo asset to take away.
That second audience deserves attention. The person who attends a sales meeting may have to explain the purchase to colleagues who missed it. A product experience that can travel has a different job from a presentation controlled by its author. The software must do some explaining on its own.
For Stevenson’s founding idea, the distinction offered another practical test. Could the experience remain useful after the person who prepared it stopped narrating? A successful handoff asks a product to withstand the wonderfully inconvenient fact that other people will use it in their own way.
The two uses also put pressure on the editing experience. A team needs enough freedom to make the example relevant, and enough consistency for the next colleague to recognize what has been prepared. That balance belongs to the everyday mechanics of selling software. It gives the founding idea a continuing assignment beyond the first successful demonstration.
Seen this way, the demo becomes a piece of shared work. The engineer, the salesperson and the prospective user all have a stake in whether it makes sense. Stevenson’s business put a tool at that meeting point, where a small change in preparation could affect several people’s time.
The enthusiasm, and the question underneath
Stevenson’s public excitement about Reprise was hardly concealed. In a LinkedIn post about the Series A period, he wrote: “In my entire career I’ve never felt the stars align like this”. The post connected the opportunity with the team, the problem and the fit between product and market.
There is a human detail in that list. For a repeat founder, the problem itself can be part of the attraction. An irritating task offers something definite to work on. A team with shared experience offers people who already understand why the irritation deserves attention.
His Reprise chapter has the large numbers expected of a funded software company. It also has a smaller and more revealing unit of measurement: a person trying to get through an ordinary task. The founder’s idea had to survive contact with that person’s schedule, preferences and willingness to try again.
There is room for a little humor in the mismatch Stevenson chose to address. The company selling a way to make work easier can face considerable work preparing to explain itself. The people who write the software may then be asked to help demonstrate how little assistance the customer will require. A useful demo tool can spare everyone some of that circular conversation.
Stevenson helped start Reprise around that preparation problem. The first ten customers then helped test the answer. Their part in the story gives the financing rounds and product announcements a practical foundation: people had to find a place for the software in their working lives. The next demonstration, and the one after that, would give them another reason to decide.