David DeRam and the case for alligator blood

Four people were sitting around a table in the first week of Greenlight Guru when the conversation turned to software validation. The chief technology officer took in the requirements and offered his assessment: “I quit.” David DeRam tells the story with an immediate qualification. The CTO was joking. Still, a joke can be a useful early warning system.

DeRam reached for a scene from Rounders, the poker film, and its phrase “alligator blood.” Here was a way to describe people who could absorb setbacks and continue competing. The expression stuck. Years later, during a conversation about the company’s first decade, an alligator picture with those words was visible behind him. A difficult meeting had acquired a mascot.

The founding problem was already clear: assemble people who could keep working through something difficult. DeRam had found a memorable way to describe them.

A consulting job, then a leap

Before Greenlight Guru, there was a young consultant trying to find his footing abroad. DeRam has described arriving at Toshiba in Düsseldorf at 21, unable to speak German. Subsequent assignments took him to Toyota in Australia, San Francisco and Simon & Schuster in the United Kingdom. His early working life involved considerable movement before entrepreneurship supplied a different sort of uncertainty.

His education had already mixed disciplines. At Indiana University Bloomington, where he studied from 1987 to 1991, he was an Evans Scholar and competed in the Little 500 cycling race. His public profile lists computer science, business and math. The combination makes a useful backdrop to a career spent moving between technical work and the business of getting people to do it.

Leaving consulting meant giving up an existence he remembered as comfortable. In his telling, starting a company resembled jumping out of a perfectly serviceable airplane. He has never been especially delicate about the difficulty of that choice. The public version of DeRam is an enthusiastic builder who also remembers that the building can be miserable. That gives his encouragement some texture: he knows what the invitation costs.

The lunch that overran

In 2012, Matt Hunckler met DeRam for sushi before a public conversation with Indianapolis entrepreneurs. A quick introduction became a three-hour lunch. At that point DeRam had already been involved in building six software companies over roughly fifteen years. A short meeting was perhaps an optimistic scheduling decision.

The ideas he brought to the stage were practical. Decide where to commit scarce resources. Keep developing. Build the working environment you want to inhabit. His first company, as the story was told then, had begun with a sketch on a diner napkin. The glamorous artifact was disposable; the consequential part was deciding to proceed.

He liked to ask his team to find the quickest route to completing a task. It is a revealing approach because it asks for a method. Speed becomes something the team has to design. The deadline alone cannot do the work.

That early conversation also supplies a useful check on the later alligator motif. Persistence, for DeRam, had been a preoccupation before Greenlight Guru gave it a name. The reptile arrived after the habit.

“What is the fastest way we could get that done?”David DeRam, 2012

Two hundred conversations before the pitch

Greenlight Guru was founded in 2013. Jon Speer brought a closely observed problem and kept bringing it to DeRam. DeRam remembers the persistence stretching over three years. They attended a trade show together, where the intensity of prospective customers helped make the opportunity tangible. It is easier to understand a market when the people in it have been waiting for someone to listen.

By the company’s 2015 launch announcement, the team had conducted more than 200 interviews with prospective users. Those conversations identified frustration with complicated, awkward software that required too much customization. The proposed answer was a focused platform with a simpler experience.

The company secured $1.25 million and launched its quality management software. During the previous year, it had tripled its team, released a beta and signed its first paying customers. These are modestly sized milestones beside the financing that would follow. They are also the milestones that turn an idea into an enterprise with obligations.

DeRam emphasized the team when asked what made the business different. His examples of what a capable group might accomplish ranged from a software company to a bake sale. The scale changed; his faith in the group did not. Even the bake sale, apparently, deserved competent leadership.

Recruiting the right dressing room

By December 2015, DeRam was explaining team selection through another sporting reference: the American hockey team of 1980. Putting a standout in every position was insufficient. The players needed to work together, respect one another and care about the group. He wanted colleagues who would play for each other.

The same interview reveals a founder interested in details that rarely make a fundraising headline. He wanted a complicated product to feel as approachable as LinkedIn. Designers and user experience specialists were part of making that happen. The accumulated knowledge inside the company had to become something a customer could actually use.

He also described helping customers with introductions to investors and with pitch strategy. Relationships were part of the offer. A software subscription could open a conversation about a business problem beyond the screen.

His account of growth repeatedly brings the reader back to these small interactions: an introduction, an easier workflow, the right colleague in a difficult discussion. The theatrical language makes him memorable. The underlying management work is surprisingly concrete. Someone still has to choose the people, refine the interface and pick up the phone.

A much larger set of obligations

In June 2021, Greenlight Guru received a growth investment of more than $120 million from JMI Equity. DeRam’s company had reached a different order of magnitude. The investment announcement described more than 500 customers worldwide and a headcount that had nearly doubled over the preceding year.

The stated uses for the capital included faster product development, expanded capabilities and global growth. DeRam described the selection of an investment partner as deliberate, with customer priorities central to the decision. Money came attached to a plan for what the organization would have to become.

In Indianapolis, that expansion had a visible setting. Greenlight Guru’s new headquarters occupied the top two floors of Union 601. The financing could help support hiring into the new space. The company that had once been celebrating a handful of paying users now had to coordinate a substantially larger operation.

A large financing round is a crisp public event. What it asks of a founder is less tidy. More customers create more promises. More colleagues create more relationships to maintain. DeRam’s long-running interest in team behavior had become an operating concern on a much larger scale. The alligator now had rather more people depending on it.

The finish line was exactly 2,000 meters away

That same year, DeRam supplied an unusually literal test of his appetite for difficult tasks. He placed tenth in the 50-54 age group at the C.R.A.S.H.-B. World Indoor Rowing Championships, racing over 2,000 meters. The qualification matters: this was a result in a specific age category and event, with an actual finish line.

His preparation involved twelve weeks of training, six days a week. He worked with Kevin Bailey, the founder of Dreamfuel, on the performance side of the attempt. DeRam connected the race to the values he wanted colleagues to practice: doing demanding work and discovering that an apparently fixed limit might move.

An indoor rowing machine makes a stern companion for a software executive. It offers no interest in the pitch deck. There is a distance to complete and a result to record. For someone fond of athletic language in business, entering the event meant submitting his own performance to a comparatively simple test.

There is a court behind the metaphor

DeRam’s connection to basketball goes beyond borrowing the language of a coach. He founded the Progeny Foundation, which supports young players in Indianapolis. His public profile dates that involvement to 2007. In 2023, the Indianapolis Business Journal described a $10 million investment in a private youth basketball facility, funded through the foundation and contributions from clients and partners. The arena had opened the previous year.

The foundation’s program combines basketball development, academic tutoring and life skills. Its Guru Arena includes full-size courts and specialized shooting technology. Players receive individual academic support alongside opportunities to develop their game and meet college recruiters.

Here the recurring ideas acquire a physical address in the community: provide a setting, bring in expertise, help people prepare for an opportunity. A young player needs somewhere to practice and someone to notice what needs work. Academic support is part of the arrangement, because the college ambition extends beyond the court.

The foundation gives DeRam’s talk about developing people a more specific meaning. There are facilities to maintain, tutors to provide and young athletes with their own plans. The beneficiaries have a future to build that will not be measured in software subscriptions.

Another seat at the table

On August 27, 2024, Greenlight Guru announced Ed Holmes as its next chief executive following a national search. DeRam would move to executive chairman of the board. Holmes arrived with experience leading other software businesses, and DeRam publicly endorsed the appointment.

The change gives the story a useful pause. A founder who had spent years choosing colleagues and talking about teams was handing the chief executive’s job to another operator. The company would continue with a different person leading its daily work.

Across the consulting assignments, early companies, customer interviews and basketball program, DeRam keeps returning to the conditions that allow people to improve. His methods can be theatrical. An alligator on the wall is a memorable accessory for an enterprise software discussion. But the commitments underneath it are recognizable: choose carefully, prepare seriously and remain useful when the work becomes difficult.

The joke at that first table has lasted longer than most meeting notes. Its durability says something about DeRam’s gift for giving a group a shared language. Everyone can remember two words. Then comes the harder part: coming back to the table and doing the work.