Ryan Glasgow and the question the dashboard couldn’t answer

Launch day ought to have been the pleasant part. At Weebly, a new iOS app was attracting tens of thousands of downloads and attention from the technology press. Ryan Glasgow, a product manager, had a less festive assignment: work out what was going wrong for the people actually using it. Bugs and awkward edge cases had survived testing. The CEO wanted answers on Slack. A successful announcement had acquired a rather demanding sequel.

Glasgow could hardly arrange two thousand customer calls. He put a short survey inside the product, asked users about the trouble where it occurred, and typed their answers into a spreadsheet. Then came sorting, prioritizing, and handing the problems to engineering. Within weeks, the team had cleaned up the issues. It was a useful rescue operation. It was also an unusually good advertisement for a business that did not yet exist.

The episode contains much of Glasgow’s later career in miniature: a product has shipped, its users have something to say, and someone must turn their experience into a decision before the next release. That someone was him. The spreadsheet worked, but the human labor behind it was difficult to repeat. Each new response improved the evidence and added another little job.

Now the founder and CEO of Sprig, based in San Francisco, Glasgow has spent years trying to shorten that journey. His company began as UserLeap and became Sprig. The ambition has widened from brief surveys inside software to research infrastructure powered by agents. The original predicament remains recognizable. A team can know an extraordinary amount about its customers and still struggle to understand them.

An answer filed under “Other”

Before Weebly, Glasgow worked across young companies including Extrabux, GraphScience, Livefyre, and Vurb. All five businesses in that early career, counting Weebly, were eventually acquired. He entered startup work while still in college and attended the University of California, San Diego. His professional education also happened in the considerably less orderly classroom of products people could choose to ignore.

He joined Vurb as its first product manager in December 2011. The consumer app was built around search, discovery, and sharing. Glasgow asked early users which features they wanted and what needed fixing. The useful surprise appeared in the space the questionnaire had left for “Other.” Customers valued curated content more than the search function the team had emphasized. They were answering a question the available choices had failed to ask.

That is an awkward discovery for anyone who has spent time composing a tidy list of options. The users have declined the invitation to agree with your understanding of the problem. Glasgow’s team changed the experience to emphasize finding other people’s content. He later reported a 74 percent improvement in retention after those changes. The number belongs to that Vurb episode, rather than to a general promise about surveys.

The lesson was concrete: an open response could expose a mistaken premise. A click tells you which offered answer somebody selected. A sentence can tell you why the whole menu is wrong. For Glasgow, leaving room for that sentence became part of the work. It is a small design decision with rather large consequences for the confidence of the people reading the results.

When listening became a volume problem

Glasgow moved to Weebly in 2014. At a much larger company, the personal attention that worked with a handful of early users became harder to sustain. Analytics could reveal a drop in conversion among sellers or identify a group leaving the product. It could make the question precise. It could not supply the explanation simply because the chart had excellent resolution.

That gap gave his work an uncomfortable rhythm. The team needed answers quickly, while careful reading and grouping of written feedback took time. By the time research caught up, a release could already have gone out. Software development had acquired faster instruments; the process of hearing from customers still involved a person doing a substantial amount of reading.

One Weebly power user made the problem especially memorable. Glasgow recalled a free customer called Sean who found his Facebook profile and sent feature requests. Sean was certainly available for comment. Availability, however, did not make his preferences representative of paying customers. A persistent correspondent could become a very efficient way of misunderstanding a quieter population.

There is an everyday social difficulty here as well as a technical one. A vivid complaint has a speaker, a tone, and perhaps a follow-up message. An unvoiced need has none of those advantages. Glasgow’s response was to pursue a more systematic way of collecting feedback. The point was to give product teams a broader basis for judgment than the most energetic person in their inbox.

A company built around the unfinished work

After Weebly’s acquisition by Square, Glasgow took time off and traveled. The missing tool kept coming back to him. Sprig’s founding is generally dated to 2019, following his earlier exploration of the idea. He had seen the same difficulty from different distances: first with small groups of users, then inside a business with millions of accounts. The scale changed; the unanswered questions persisted.

An early colleague was Kevin Mandich, whose machine learning work addressed the labor of interpreting written responses. Collecting comments and understanding them were separate problems. A survey could make the first one easier while making the second one larger. Building analysis into the product gave the company a reason to exist beyond providing another place to write questions.

Glasgow also had to learn selling. His previous companies had not given him experience working alongside a sales team. Early on, he met prospects individually and used their business numbers to discuss the potential value of improved conversion or reduced customer loss. In an early interview, he said his favorite business book was Richard Rumelt’s Good Strategy Bad Strategy. The preference fits those conversations: choose a particular problem and establish why it matters.

The first customers brought more than contracts. They supplied a test of whether the product could earn a place in real work. Investor Daniel Levine described UserLeap in 2020 as bringing faster, more granular, iterative research into the product itself. That framing captured the intended customer: someone who already had decisions to make and needed evidence soon enough to influence them.

Money, a new name, and some manners

In December 2020, Glasgow announced a $16 million Series A led by Accel. With earlier backing, the disclosed total reached $20 million. He named supporters including First Round Capital, Elad Gil, Figma’s Dylan Field, Looker co-founder Ben Porterfield, and Notion’s Akshay Kothari. The connections crossed the same product world he was trying to serve. People building software were financing a tool for understanding its users.

In 2021, UserLeap became Sprig as the company expanded its research offering. The old name had accompanied a microsurvey product; the new one accompanied a broader collection of tools. Glasgow’s announcement described more than four million survey responses captured for over six hundred companies. Those were figures at the time of the announcement, a marker of how far the early experiment had traveled.

Growth raises a delicate question for a survey company: how much asking is too much? Glasgow’s advice has included a kind of digital etiquette. Wait until someone finishes an activity or leaves a flow, rather than interrupting halfway through. Begin with an easy, closed question and then invite an explanation. Keep the exchange short. Even a sensible research objective does not grant unlimited rights to somebody else’s afternoon.

He has also urged teams to pick an immediate decision instead of trying to study everything at once. This gives research a destination. A question attached to an upcoming decision can change what happens next; a sprawling questionnaire may mostly produce another sprawling document. The restraint is useful. A company selling the means to ask questions needs to remember that its customers’ customers came to accomplish something else.

Empathy with an operating procedure

When asked in 2024 about the important skill for a founding product manager, Glasgow chose empathy. He described understanding both the customer’s problem and whether a proposed solution actually solved it. He extended that responsibility to employees and investors in his work as CEO. This is a fairly demanding definition. Sympathy is easy to express; testing your preferred solution against somebody else’s experience is less comfortable.

Sprig has used its own tools to make decisions. To prioritize integrations, the team surveyed people engaging with its integrations gallery about what they valued and wanted next. Their answers pointed toward new destinations for exporting and analyzing responses, helping shape the decision to partner with tools such as Mixpanel. The listening mechanism applied to the company selling the listening mechanism.

Glasgow has also described co-creating a survey question type with a financial technology customer, involving that customer in specifications, designs, and the first trial. The story is modest enough to be instructive. A customer relationship becomes part of product development through several specific exchanges. The word empathy earns its place when it changes what gets built and who gets to examine it.

His public conversations return to access as well as collection. A researcher may understand a study deeply, yet colleagues still encounter only a finished report. Glasgow wants the evidence to remain available for follow-up questions. A presentation can settle into a drawer with remarkable dignity. Data that people can interrogate has a better chance of returning to the conversation.

“Across my five startup experiences as the founding PM, empathy for the customer has been the most important skill.”Ryan Glasgow

The eager intern gets a larger desk

By 2025, Glasgow was discussing AI as an eager intern: quick and willing, but in need of direction and review. That image gives the researcher a recognizable role. Break the work into steps, decide which tasks can be delegated, and inspect the output. An intern can help prepare the material. Someone still has to decide whether the conclusion deserves to leave the room.

In June 2026, he announced Sprig’s Model Context Protocol connection, allowing research data to be accessed from AI tools including Claude, ChatGPT, Cursor, and Gemini. The practical aim was to reduce exports and copying between systems. It also extended an older concern of his: evidence should be available where decisions happen, rather than requiring every colleague to visit the place where it was collected.

On October 8, 2026, Glasgow previewed the upcoming Analyze Agent. The planned tool would recommend and run statistical analyses, support follow-up investigations, and move findings into reports. It was announced as coming soon. Researchers would retain access to methods and settings, with AI optional. The promise joined quantitative analysis to the other stages of a study while preserving a way to inspect the work.

The trajectory is easy to trace back to that Weebly spreadsheet. Glasgow once collected answers, sorted issues, and sent the findings to engineers himself. Each task has become a candidate for software assistance. His aspiration is to let researchers direct more of the investigation while agents carry out portions of it. The useful test will be the same one that faced the young product manager: can this help a team understand what happened, and make a better decision before the next thing ships?