Ross Rich and the trouble with a perfect playbook

Ross Rich once hand-delivered a bottle of champagne to a customer. Dan O’Holleran, then at Okta, had closed his first big deal using Accord, and Rich thought the occasion deserved a visit. For a founder selling software to make sales more repeatable, it was an enjoyably personal errand. Somewhere between the workflow and the celebration, a person had done something worth noticing.

Rich used the episode to explain a tension he knows well. A young company can give its first customers attention that becomes harder to sustain as it grows. The attention still matters. So does finding a way to serve the next customer without exhausting the team. A bottle has a fairly obvious delivery process. Care is trickier to put into a system.

That difficulty runs through his career. Rich, the Canadian co-founder and CEO of Accord, has worked in music marketing, sold payments software and built a company with his brother. His recurring interest is what people actually do with an idea once the presentation is over. A fine strategy has to make it through the afternoon.

A record deal, then a different kind of deal

In November 2014, Rich was graduating with a commerce degree from the University of Victoria’s Gustavson School of Business and already working as a marketing assistant at Columbia Records in New York. He had started an artist-management firm the previous year. Its roster included fellow student and singer Jade Tjorhom.

The music business had grown out of doing music. Rich and his brother Ryan performed rap, and the pair helped establish the production and promotion company Victorious Events with fellow commerce students Code Workun and Tanner Manning. His university memories included a household full of entrepreneurial conversation, with Ryan and roommate Devon Vivian discussing businesses and business biographies.

“I mean, here I am in New York…I can’t believe it,” he said at the time. There is something pleasing about catching a career before hindsight tidies it up. New York was the destination. Columbia was the dream job. Payments software had yet to enter the plot.

Later, his account of the music industry acquired a sharper comic edge. He had imagined himself as Ari Gold, the formidable agent in Entourage. The actual experience, he said, felt closer to being Gold’s assistant, Lloyd. A supposedly creative business involved bureaucracy and limited access to decisions. Rich wanted more of the entrepreneurial activity that had drawn him there.

He joined Stripe in 2015 as an early seller and went on to work in business development and partnerships. There, the work could involve technical questions alongside the business consequences of accepting payments across markets, currencies and payment methods. Helping a customer make a decision required more than a tour of the product. The commercial and technical conversations had to connect.

The drawing before the software

The beginning of Accord contained a useful limitation: the prospective founders could sell an idea, but could not immediately build the application they imagined. Rich drew it instead. In early demonstrations, someone could pretend to press a button and he would move to the next page. The interface had an unusually cooperative loading mechanism.

He has described those conversations as a way to understand what people would find useful before committing to a product. The drawings made a proposal concrete enough to question. They also kept it cheap to change. In an industry inclined to admire the finished object, a page turn can be an underrated research instrument.

Accord was founded in 2020 and joined Y Combinator’s winter batch. Rich’s brother Ryan was a co-founder, alongside technical co-founder Wayne Pan. The family partnership had already survived college entrepreneurship and performing together. The brothers had opened for Bone Thugs-N-Harmony, a career milestone Ross still recounted with amusement. Software offered a new kind of audience participation.

The first pitch was about making a purchase easier to coordinate. In 2021, Rich described shared spaces containing next steps, milestones, resources and the people involved in a decision. The buyer and seller could work from the same plan, rather than reconstructing it from email threads. Even the name of the problem carried a shift in perspective: the customer had work to do, too.

Fifty customers and a few wrong assumptions

Accord entered 2021 without paying customers. By the time Rich reflected on the year in January 2022, it had signed more than 50 and raised $7 million in seed financing. Those numbers came with a less photogenic achievement: abandoning assumptions that had sounded reasonable at the beginning.

He had expected large enterprise sales teams to be the immediate fit. Earlier-stage, fast-growing startups proved more receptive. He had also expected prospects to need extensive guidance to understand the product. They wanted room to explore, supported by trials, case studies and useful information. The person selling a better buying experience had to keep revising his own.

His reflections distinguished design partners, who were willing to help develop an idea, from customers who needed a product to solve a business problem. Affection for a promising company and a reason to pay it are different commercial conditions. A founder benefits from knowing which conversation is taking place before deciding what the enthusiasm means.

When Accord announced that round, Rich wrote about early customer calls, first wins and the people who had helped. Berlin joined the board. He singled out her interest in product, thoughtfulness and integrity as qualities he wanted in a partner. The announcement also set out practical plans: hiring, developing the product with customers and building partnerships.

A bottle at the door

The champagne delivery belongs to the same account of company building as the financing. Rich’s point was that repeatability and personal attention have to coexist. One makes growth possible; the other gives a customer a reason to remember the experience. The argument becomes more persuasive when the founder is willing to carry the bottle himself.

Reflecting on 2024, he described a more deliberate effort to show customers that Accord cared. The team met people in person earlier, visited after contracts were signed, attended customers’ sales kickoffs and brought customers together to learn from peers. These were changes in conduct, with demands on someone’s calendar, rather than another adjective for the website.

He also acknowledged that he had not been ready for everything leadership required when he started. Failure had forced him to develop. That admission gives the customer stories some weight. The founder is describing practices he had to learn, with a company depending on whether he learned them well enough.

The founder who kept asking questions

In November 2021, Rich introduced From Vendorship to Partnership, a podcast designed around conversations with people who had already faced the decisions occupying him. He wanted experienced operators with strong views and practical detail. The attraction was fairly straightforward: starting a company presented enough unfamiliar problems without volunteering to rediscover every answer.

The title expressed an aspiration for Accord as well. Rich wanted commercial relationships to involve transparency, collaboration and an interest in the other party’s needs. The same approach, he argued, could shape hiring, communication and the way a company worked with people beyond a sale.

By February 2022, he had interviewed 12 founders and leaders for the first season. Then Ryan interviewed him about what he had learned. The recap returned to understanding customers and building relationships with a team. It also gave room to other founders’ different experiences, rather than making every conversation an endorsement of one method.

There is a useful discipline in hosting that kind of discussion. A chief executive usually has a proposal to defend. An interviewer needs to leave enough space for an answer that might complicate it. Rich’s public work contains both impulses: the enthusiasm of someone making a case, and the curiosity of someone still collecting better questions.

“When excellence is the path of least resistance, culture shifts.”

Ross Rich · December 2025

The playbook has to leave the shelf

By December 2025, Rich was explaining Accord’s revised brand through a story about a company that had spent half a million dollars on a value-selling consultant. The framework and materials had impressed leadership. Six months later, the sales results had scarcely changed. His criticism concerned the distance between an agreed method and its everyday use.

Accord’s answer was to put business cases, stakeholder engagement and shared plans inside the work of running an opportunity, with intelligence features helping complete the tasks. Rich’s ambition was to make useful habits easier to follow consistently. That remains a demanding proposition. A company selling better execution has given customers a particularly concrete way to judge it.

In August 2026, he was still discussing the human part of that problem. His view was that AI could make capable sellers more efficient without automatically improving the middle of a team. Leadership, a shared language and a workable process had to come first. Faster access to information did not settle the question of what someone should do next.

He also described his own difficulty handing sales to other people. Familiarity had made the work seem obvious, and he had stepped away too early. He called it the curse of knowledge. The founder selling a system for transferring good practice had encountered the problem inside his own company. It is a useful place to end up: close enough to the work to remember why the system needs to exist.