Jim Eberlin needed an engineering team. He could have bought the usual stack of résumés, paid the usual recruitment fees and asked the usual questions. Instead, he helped turn a winter weekend in St. Louis into an audition. The candidates would build something. He would watch.
At the first GlobalHack in 2014, Eberlin’s new company, TopOPPS, sponsored a programming competition. Over Super Bowl weekend, developers worked on a business problem while a potential employer got to see the things interviews tend to conceal: who could organize a team, who could finish, who could make an unfamiliar group function.
Afterward, he invited 18 engineers to a private dinner and networking event. By February, he had hired five participants and wanted more. He called the process “Interviewing 3.0.” Somewhere in the history of recruitment, a question about somebody’s greatest weakness had just lost a little of its authority.
The episode is a useful place to meet Eberlin. His career is full of expensive business problems approached from an unexpectedly practical direction. Financial planning became Host Analytics, later Planful. Customer retention became Gainsight. Sales forecasting became TopOPPS. More recently, the nuisance of getting answers out of business software has brought him to InsightHive.
The interview lasted a weekend
The hackathon hiring story became more interesting as the year went on. By November 2014, TopOPPS had hired ten participants to form its development team. Winning the competition was not a prerequisite. Eberlin was recruiting colleagues, and a prize table could tell him only so much.
Sam Cummings had joined strangers and emerged as their leader, despite his team missing the final round. Rick Christianson, a longtime IBM developer, had entered for a chance to meet local programmers. He worked alone, produced a prototype and did not win. He subsequently became TopOPPS’ engineering director.
There is a small distinction here with large consequences. A competition chooses a winner under a set of rules. A founder has to choose people who can live with the consequences of next month’s rules changing. Watching participants solve problems offered Eberlin a different kind of evidence from a polished account of their previous jobs.
Engineers invited to a post-hackathon networking event.
TopOPPS’ 2014 recruiting experiment
Before the software, the customers
Eberlin’s education was in business and accounting at Maryville University. Consulting supplied another kind of education: close contact with how companies actually worked. A consulting business that took hold gave him both the idea and the money to start his first product company.
Host Analytics arrived in the early 2000s, addressing the financial planning work that companies needed to repeat, reconcile and defend. Budgets are rarely anyone’s idea of a dramatic opening scene. Yet a business that cannot explain its numbers has a fairly immediate plot problem.
The company’s proposition put financial planning and reporting into a cloud service. This was the territory of finance departments, established vendors and systems that were already embedded in corporate life. Selling a new approach meant persuading a buyer to trust a younger company with work that could not simply be postponed.
One win stayed with Eberlin: securing Procter & Gamble as a customer against Oracle, alongside partners Sreedhar Peddineni and Ric Ratkowski. It is a concrete answer to a question founders hear often: who has trusted you already? An enterprise customer can provide more than revenue. It gives the next conversation a different starting point.
In 2015, Missouri Governor Jay Nixon recognized Eberlin with the Governor’s Entrepreneur of the Year Award. Maryville celebrated his three-startup record the following year. The accounting graduate had spent his career moving from the work inside businesses to the software sold to them.
A new seat revealed another business
Building Host Analytics also required Eberlin to change his own job. He brought in a Bay Area chief executive and became chief customer officer. That shift put him closer to a problem that would become the basis for Gainsight: helping customers use what they had bought and find enough value to remain customers.
He also had to learn a different audience. On one early fundraising trip, he made eight pitches in three days. His first went badly enough that an investor coached him. The final two produced term sheets. The story is a welcome complication to the tidy founder biography, in which competence generally arrives fully dressed.
JBara Software became Gainsight. In 2013, Nick Mehta joined as CEO after an introduction through Battery Ventures. Mehta described a company that had already attracted customers including Marketo, Informatica, Xactly and DocuSign before venture funding. Eberlin and his team had something tangible to put in front of an incoming leader.
Mehta also described finding common ground with Eberlin on the company’s values. They settled on the Golden Rule, Success for All and Child-like Joy. The last is an unusually cheerful item to encounter in enterprise software. It suggests there was room in the project for something beyond another meeting about renewals.
“I’ve done three companies now and the recipe was never the same.”
Jim Eberlin, 2021
That caution matters when reading his career backward. Three acquired businesses can make the sequence look inevitable. Eberlin has said that trying to apply the recipe from an earlier company was itself a mistake. Experience gave him reference points. It did not relieve him of the need to look again.
Three companies, three different questions
A reading of the business problems behind Eberlin’s three acquired software ventures.
TopOPPS, founded in 2014, tackled the uncomfortable distance between a sales pipeline and a dependable forecast. A list of opportunities is useful. Knowing which ones are likely to become revenue is considerably more useful, especially when somebody expects you to defend the number.
The company applied artificial intelligence to pipeline management and forecasting. On March 10, 2021, Xactly announced its acquisition of TopOPPS, adding those capabilities to its revenue software. The transaction placed Eberlin’s third product business inside another company’s broader offering.
The other businesses had already reached their own transactions. Vector Capital completed its acquisition of Host Analytics in January 2019. A year later, Host Analytics changed its name to Planful. In November 2020, Vista Equity Partners acquired a majority stake in Gainsight in a deal valuing the business at $1.1 billion.
Those dates describe company milestones. They also reveal the time involved. Products keep developing after their founders change roles. Other executives, employees and investors carry the work forward. The name a customer recognizes today may have appeared years after the original business began.
St. Louis remained part of the equation
Eberlin’s work connected St. Louis with Bay Area investors and management teams. The familiar technology story asks when a founder will leave home. His account contained a more domestic constraint: his wife had made clear that she was staying. He built a way to work across the two places.
The hackathon hires gave that arrangement substance. Talent was something he could recruit locally and show in action. TopOPPS offered an example of building a team through participation in the city’s technology community. The people who gathered for a competition became colleagues with a product to deliver.
After the acquisitions, his involvement extended into mentoring and angel investing, including work with Arch Grants and OPO Startups. In 2022, he received a Lifetime Achievement Award in the Startup Exit Awards. He has also served as an executive advisor at Thompson Street Capital Partners.
A lifetime award is a slightly awkward accessory for someone still starting things. It sounds as though the office ought to be packed up. Eberlin’s subsequent work has been concerned with what happens when software arrives at a customer’s office and the difficult part begins.
The next problem was already in the product
I-SERV, which Eberlin founded, provides implementation and optimization help for platforms including Gainsight and Xactly Forecasting. Its rationale is straightforward: access to a tool does not automatically give a team the ability to use it well. Delivery, configuration and working habits still matter.
InsightHive follows a related frustration. In a December 2025 account of its origins, Eberlin described customers wanting reports and dashboards without leaving their application. Earlier teams had built an embedded reporting tool called Data Studio. The new venture takes that recurring need into AI-powered analytics.
Its intended customers are other business-software companies. The offering combines embedded reporting, natural-language questions and data integration. The practical ambition is to let their product teams provide analytical tools without constructing an entire analytics business inside their existing one.
That leaves Eberlin close to the concerns that started the earlier ventures: a customer trying to finish a task, a team trying to make sense of its data, an engineer trying to avoid rebuilding the same machinery. The technology has changed. He keeps returning to the point where the work becomes unnecessarily difficult.
Back at GlobalHack, that point was hiring. He wanted to know how people worked, so he found a way to watch them work. Years and several company names later, the question still suits him: what could you learn by getting closer to the problem?
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