Conway Teng and the Trouble with Getting Paid

A commission is a small promise with a surprisingly large administrative staff. A salesperson makes a sale. Someone else must establish which sale counts, which rate applies and whether the number on the statement agrees with the number in the plan. Conway Teng had been on the receiving end of that assignment. He knew how much work could hide inside a percentage sign.

Before CaptivateIQ, Teng had managed commissions with spreadsheets and older software. When he reconnected with Mark Schopmeyer, a friend from the University of California, Berkeley, they discovered a shared grievance. Both had spent time administering compensation. Both thought the tools were inadequate. There are friendships sustained by music, sport or good restaurants. This one found a business in the mechanics of paying salespeople.

In 2017, Teng, Schopmeyer and another Berkeley friend, Hubert Wong, founded CaptivateIQ. Wong became its chief technology officer. Teng and Schopmeyer shared the chief executive role. Their starting point was unusually concrete: they wanted software they could have used in their previous jobs. The customer they were trying to understand was someone whose desk they had already occupied.

“We ultimately quit our jobs to basically build out the tool that we would have wanted to use,” Teng said in 2020. The sentence contains very little theatre. It also explains the company's first advantage: an intimate acquaintance with an expensive nuisance.

An apprenticeship in how businesses work

Teng arrived at that nuisance by a route through both finance and startups. His career included corporate finance work at McKinsey, helping launch the loyalty rewards business Fivestars, and finance and go-to-market leadership roles at Gusto and OrderAhead. Those businesses dealt with different customers and different transactions. Together, the roles put him close to the practical machinery of running a company.

That background matters to the kind of product he went on to build. A compensation plan must survive contact with sales records, payment rules and the people who need to interpret them. A beautiful model can still become an awkward monthly ritual. The work sits between departments, which gives a misunderstanding several places to hide and a generous supply of people to inconvenience.

CaptivateIQ entered Y Combinator's Winter 2018 batch. Its own company history places its first paying customer, first employee and San Francisco office in that year. These are modest milestones beside a large funding announcement, but they are closer to the founder's original test. Someone else had to find the problem painful enough to pay for the proposed repair.

One early hire supplied another view of the founders’ beginnings. Christian Borrelli later recalled joining in 2018 as the first employee without having met them in person. People around him questioned both the decision and the market’s potential. In 2023, after five years leading and growing the sales organization, he described the experience as the most challenging and rewarding period of his career. The recollection brings the early company back down to the scale of an individual choice. Before there was a large customer base, there was someone deciding to join three founders he had yet to meet.

The product also had to become easier to use. Its first version required SQL knowledge. Working with early customers, the founders developed a second version around building blocks and a no-code or low-code approach. That change put more of the work within reach of the people administering plans. Knowing a customer's problem and giving that customer usable controls turned out to be separate jobs.

Two executives, room to go deep

In the company's early division of responsibilities, Teng concentrated on product, while Schopmeyer handled finance, fundraising and go-to-market strategy. The shared title gave each room to spend more time within a part of the business. For a founder building tools around complicated rules, depth had an obvious attraction. Broad responsibility can otherwise become a very efficient way of attending meetings about everything.

Schopmeyer later described a practical benefit of their arrangement. When he needed to take a hands-on role in a department during a transition, Teng kept the sales team supported and decisions moving elsewhere. The account offers a useful glimpse of Teng at work: maintaining continuity while his counterpart concentrated on a particular problem. The arrangement depended on the rest of the company continuing to function.

Schopmeyer has also described the principles they developed together: exchange complete information, keep communication moving, debate decisions and return difficult choices to customer value. These are working agreements with consequences for ordinary days. Two people can share a title quite easily. Sharing enough context to make decisions without repeatedly stopping the company requires more deliberate effort.

CaptivateIQ's current leadership roster lists Teng as CEO and Schopmeyer as president. Their years as co-CEOs remain an instructive part of the story. Teng's public career contains a long collaboration, with roles that developed around the work the business needed.

A bigger number, the same awkward calculation

The financing followed. Sequoia led a $13 million Series A in 2020. Accel made its initial investment in 2021. In January 2022, CaptivateIQ announced a $100 million Series C led by ICONIQ Growth, Accel and Sequoia, with Sapphire joining as an investor. That round valued the company at $1.25 billion and brought its reported funding to $164.6 million.

Those are company figures, attached to a particular financing. Their significance here is the distance travelled from a familiar office frustration. A job that Teng and his co-founders had wanted to stop doing manually had become the basis of a business with institutional backing. CaptivateIQ now reports more than 1,000 customers worldwide.

The product's appeal included a careful compromise. It retained the flexibility and familiarity that made spreadsheets useful, while automating the labor around them. That is a more demanding brief than simply declaring a spreadsheet obsolete. People keep spreadsheets because they can change them. A replacement has to accommodate the exceptions that made a tidy original plan untidy.

The next chapters extended that idea. In 2023, CaptivateIQ introduced SmartGrid data-management and calculation capabilities. In September 2024, it launched CaptivateIQ Planning, connecting territory and quota planning with incentives. The company was reaching further into the decisions that determine a seller's working year: the accounts assigned, the target expected and the reward attached.

The questions hiding inside an average

Teng's own writing helps explain what interests him beyond the mechanics of a payout. In a January 2025 essay, he used an example of a business targeting a 10 percent commission rate. The average looked reassuring, while individual sellers earned rates of 15 percent and 7 percent. He presented the discrepancy as a reason to examine what the plan was actually doing.

That example is revealing because the average can be correct. The question concerns what the aggregate conceals. Teng's argument asks compensation teams to find time for that examination, rather than spend their working hours assembling payments. It is the difference between producing a result and understanding the business decisions inside it. A perfectly respectable average can be a surprisingly effective hiding place.

In another essay, published in August 2024, he warned about unrealistic quotas, irregular reviews and confusing communications. He recommended taking account of historical performance and team capacity, listening to sellers and explaining what good performance looks like. The advice gives the person receiving the commission a place in the design process. They need to understand the rules well enough to act on them.

His April 2025 discussion of consumption-based compensation took that reasoning further. When customers pay according to usage, the signature on a contract may tell only part of the revenue story. Teng urged leaders to examine how customers actually use a product, what sellers can influence and how rewards connect to those actions. The details include adoption patterns, seasonality and the timing of commissions.

Read together, these arguments describe an ambition larger than faster administration. Teng wants incentive programs to remain connected to the business they are supposed to support. That requires revisiting assumptions after the plan has been approved. The document may be finished; the customers, sellers and markets continue to move.

The next promise has an AI agent attached

At Captivate 2026 in Austin, Teng joined Schopmeyer and customer-experience leader Agata Dec to discuss the company's incentive-compensation research. One pair of findings was especially awkward: 91 percent of organizations said sellers trusted their compensation, while 64 percent reported payout errors in the previous year. Those measures describe different questions. Set beside each other, they show how confidence and mistakes can coexist.

The event also brought a new product direction into view. CaptivateIQ announced a portfolio of AI agents for compensation and sales planning, initially in limited beta. Its presentation emphasized live business data, visible actions, explainable outputs and human review. For work that affects a person's pay, those details belong in the product brief from the beginning.

An October 21 webinar listing put Teng's next theme plainly: trusted AI in revenue. The program paired his keynote with demonstrations of planning and compensation agents and a discussion with a ClickUp beta user. The sequence follows a recognizable concern in his work. A tool earns its place when the people responsible for a plan can understand and use it.

“There are no more moats. There are only head starts,”

Conway Teng · Captivate 2026

Teng said in the Captivate 2026 conversation. It is a brisk view of competition for a founder whose company grew from a stubborn, recurring task. New technology may shorten the work again. The obligation underneath it remains wonderfully old-fashioned: tell people how they will be rewarded, make the calculation understandable and pay them accordingly.