Matt Darrow went to New Zealand to get away from enterprise software. He and his wife, Dominique, bought one-way tickets after his run at Zuora, where he had helped build the technical sales organization through the company’s arrival on the public markets. There was a camper van. There was time outdoors. There was also, inconveniently, a problem he could not leave at the office.
Sales engineers helped people decide whether complicated products would actually work for them. Darrow had spent years doing and leading that work. Yet the department’s own tools were a collection of adaptations: spreadsheets, altered customer-management systems, things built because somebody needed them badly enough to build them. He began coding a prototype while traveling. The holiday acquired a deliverable.
The company that followed, Vivun, began with a practical grievance. It would eventually lead Darrow into a more unsettling question: what happens when the software you built to organize people’s work can start doing some of that work itself?
The engineer who wanted to meet the customer
Before the camper van, there were server racks. Darrow studied mechanical engineering at the University of California, Berkeley, then earned a master’s at UCLA. His research included writing software to simulate how heat moved through those racks. The technical problem was absorbing enough to study. The working life around it did not suit him.
Technology consulting at Deloitte brought him closer to the businesses using enterprise systems. At BigMachines, he found sales engineering, a profession he had not initially understood but whose combination of technical authority and commercial advice appealed to him. The customer could ask a business question; he could work through its technical consequences.
That combination helps explain the career that followed. Darrow kept moving toward the point where a product had to justify its place inside somebody else’s company. An elegant system still needed a reason to be bought. A persuasive pitch still needed a system capable of keeping the promises.
At Zuora, he built the global presales organization from the Series B period through the IPO journey, then also ran two product lines. He had seen the conversation from both ends: the people explaining what the software could do, and the people deciding what it should do next.
“Building a company is very different from building a product.”
Matt Darrow
A department hiding in plain sight
Presales is an awkward name for consequential work. It can make the job sound like something that happens while everyone waits for the proper business to begin. In practice, these are the people testing whether the buyer’s requirements and the seller’s product can meet without either side indulging in fiction.
Darrow’s argument is that these specialists have an unusually useful view. They hear objections, investigate product gaps and discover which requirements can stall an otherwise promising deal. When their observations stay inside individual conversations, the product team loses information it could use. The sales forecast loses a technical check on its optimism.
In his 2022 account of Vivun, Darrow described a platform that would capture feedback when a prospect gave it and connect that information to product teams. His ambition extended to giving presales leaders a stronger voice across the company. The people repeatedly asked to explain the product might have something to say about where it went next.
Expertise travels both ways. The conversation is useful long after the demo ends.
Four founders, two households
The early Vivun team had a domestic arrangement that tends to attract more questions than a startup’s choice of database. Matt and Dominique Darrow joined forces with John and Claire Bruce. Two married couples were building one company.
The relevant distinction was in their experience. Dominique had built customer-success teams at Google. John brought engineering and technical-sales leadership. Claire brought legal and operational experience. Matt brought the presales problem and a product leader’s understanding of it. Between them, they could build, sell, support and handle the obligations that arrive when a customer signs.
There is something pleasingly unromantic about that division of labor. A company may begin with an idea on holiday, but it soon requires somebody to read a contract. Darrow has been explicit about the machinery involved: compensation, payroll, expenses, invoices, onboarding. The less photogenic parts of entrepreneurship have an excellent attendance record.
The first check took more than a demo
Knowing a customer’s job did not automatically prepare the founders for venture capital. They sought outside feedback, including from people beyond their own network, and worked with a selected group of design partners in early 2019. They had a working product and customers before completing their first financing.
Some early investor meetings went nowhere. Funds describing themselves as early-stage wanted milestones the company had not reached. The founders had to become more selective about whom they approached, and clearer about the stage of business they were actually building.
The eventual seed financing was $3 million, led by Unusual Ventures. The lesson was humbler than the standard tale of a pitch deck provoking an orderly stampede. A founder can be convincing about a product and still spend weeks in the wrong rooms.
For Darrow, the first term sheet remained a favorite memory. He later recalled investors who confused presales with cold calling or did not understand why the profession needed its own tools. While bootstrapping, he said, he rented out his house and lived with his in-laws. Recognition of the problem had financial consequences, and very ordinary household ones.
Total funding Darrow reported in October 2024, including a $75 million Series C announced in 2022.
The buyer gets a vote
Darrow’s view of selling gives the buyer considerable agency. He has argued for putting the product in people’s hands, making objectives explicit and documenting the value created during an evaluation. The proposed purchase has to make sense to the buyer’s colleagues as well as to the person taking the meeting.
That is a more demanding standard than a friendly relationship and a well-rehearsed demonstration. It asks the seller to make the case portable. Can someone else understand what has been tested, what remains uncertain and why the purchase would help?
His advice also leaves room for patience. He has described promising initial meetings that produced no immediate next step, then returned months later as buyers better understood their own problem. In that account, follow-up has a useful job: keep the prospect informed. The passage of time need not be treated as a personal insult.
The thread running through these ideas is an engineer’s interest in proof. Selling depends on what the other organization can verify, explain internally and eventually use.
Then the tools began to change
Vivun launched VivunOne in October 2023, bringing its presales capabilities into a shared platform. The product combined workflows and information for technical sales teams, with an AI domain model underneath. It represented years of work turning a department’s scattered activities into something it could manage together.
In his December 2023 reflections, Darrow pointed to a different measure of progress: customers paying, renewing and helping the business cross revenue milestones. He discussed passing $1 million and then $10 million in annual recurring revenue. Those thresholds mattered because a product people tried had become a service organizations repeatedly budgeted for.
He also described a long-term aspiration to build a publicly traded company. Having already participated in an IPO journey, he knew something about the distance between a useful product and an organization equipped to endure. The spreadsheet problem had produced a business with obligations of its own.
A founder has to be a customer, too
By 2025, Darrow was discussing experiments inside Vivun itself. The company had reworked demand generation around automated workflows and used AI to help with technical sales and contract review. Its enthusiasm came with specific disappointments.
Website chatbots had sometimes produced inconsistent or inaccurate answers. Generated visual content still needed human judgment to finish the work. Those admissions matter in a business selling AI: installing the technology does not settle the question of whether it helps.
Darrow’s advice on adopting tools was correspondingly restrained. Pick a small number, learn them properly and add others according to the outcomes needed. There is a familiar professional irritation behind that advice. Software bought to remove friction can become another collection of things someone has to operate.
The answer moves into the meeting
In August 2026, Darrow was talking about Hero, Vivun’s AI sales teammate, and a broader change in how the company reached users. He described continuing experimentation rather than a completed transformation. For a founder whose original insight concerned the limits of existing tools, that is a consequential admission: experience can identify the problem without fixing the answer permanently.
The current proposition brings assistance into the sales conversation. Hero is designed to help sellers with questions and guidance while a call is happening. Darrow has discussed a background coaching mode as well as more visible participation. His emphasis is on the moment a seller needs expertise, when postponing an answer can interrupt a deal.
Vivun now describes its approach in terms of structuring expert knowledge: making relationships, constraints and decision paths explicit so an AI system can use them. These are the company’s claims about its method. Their practical test remains familiar to anyone who has done technical sales: does the answer hold up when somebody asks the next question?
The camper van belongs to the beginning of this story. The unfinished work has proved more durable. Darrow went looking for a way to give technical expertise a useful place inside a business. He is still working out where it should sit, who should have access to it, and how it can earn the buyer’s confidence.