Before William Boeglin was announcing investment rounds, he had an Excel problem. At Northern Trust, he built a macro-based tool to automate status reporting for its Enterprise Change business unit. Hundreds of people used it to prepare updates for senior executives. A spreadsheet is an unglamorous place to begin a founder’s story. It is also a useful one: somebody has to make the reports arrive.
The detail offers a way into a career usually compressed into three titles: co-founder, chief executive, board member. Follow the work between those titles and a more interesting pattern appears. Boeglin has kept returning to coordination: assembling people with different skills, getting software to cooperate with existing systems, and finding partners for a company’s next stage. There are larger numbers ahead. The spreadsheet deserves its moment first.
A taste for the moving parts
Boeglin attended Indiana University Bloomington from 2009 to 2013. His professional profile also lists a Six Sigma Green Belt certification from Northern Trust, a qualification concerned with improving processes. It is a fitting detail alongside that reporting tool. Both belong to the part of business where an improvement is judged by what happens on an ordinary working day, after the presentation has ended.
Early in TimeDoc’s life, he described himself as being from Indianapolis and enjoying history and business. His favorite activity was “learning new things.” Alongside the interests, he offered a concrete accomplishment: the reporting automation. He also took pride in assembling an early TimeDoc team with complementary skills. The pleasure, at least in his own account, lay in making something useful and finding people who could build it together.
That distinction matters when reading his later career. A company can be introduced through its founder’s ambition, its product, or its financing. Boeglin’s early description spends time on the machinery of working together. It is a modest starting point for a story that eventually reaches a $48.5 million round. Modest starting points have the advantage of leaving fewer ceremonial balloons to clear away.
The vacancy with a very small number
TimeDoc Health began in Chicago in 2015 and entered the University of Chicago’s New Venture Challenge accelerator that April. Its first customer implementation followed in January 2016. Those dates put a useful interval between founding and use. An accelerator can help sharpen an idea; the first implementation asks whether that idea will survive contact with someone else’s working routine.
An early recruitment notice captures the company at a more intimate scale. TimeDoc was looking for its seventh employee, who would join a development team of two. Boeglin was listed as CEO, with John DiCosola as CTO. Applicants were expected to handle full-stack development, build new features, write automated tests, and work on integrations. This was a job description with very little room for standing elegantly to one side.
The notice made “flexibility and proactivity” baseline requirements. Its practical demands explain why. A small team could hardly assign every new problem to a separate department. The incoming developer would help shape project plans as well as write code. The proposed working life was broad, unfinished, and dependent on people being willing to cross the space between their formal responsibility and whatever needed doing next.
The people on the other side of the table
Among the relationships that would shape the next stage was one with Tim Streit of Grand Ventures. Streit first met Boeglin in spring 2018. Grand Ventures subsequently led TimeDoc’s seed round. In his later account of the company’s beginnings, Streit described a founding connection involving Curtis Ginder, Boeglin, and John-Patrick Di Cosola. The business emerged through people bringing different kinds of expertise to the same practical problem.
The relationship continued across financing stages. That gives the investor connection some texture: this was a participant watching a company develop over years. For a founder, bringing in capital also brings more people into the conversation about priorities. The attraction of a check is easy to understand. The value of the accompanying judgment takes longer to establish, and depends on the particular people around the table.
In August 2019, TimeDoc announced $2.5 million in funding led by Grand Ventures, with Serra Ventures and Break Trail Ventures participating. The company said it expected to double its headcount over the next twelve months. That was a plan, rather than a completed result. It nevertheless shows the kind of task Boeglin faced: turning a growing customer business into an organization with enough people to support it.
Hiring carries its own arithmetic. Every addition increases capacity and also adds another relationship to coordinate. The seventh employee can know almost everyone’s job. Larger teams need clearer responsibilities and ways to pass work between them. The financing milestones in Boeglin’s career are worth reading with that organizational burden in mind. The announced amount is visible; the daily work of absorbing it is less obliging about posing for photographs.
Two rounds, two different scales
In May 2020, TimeDoc announced a $5.7 million Series A led by Vocap Investment Partners. The participating group included existing backers and new names, among them Impact Engine, Waterline Ventures, Chaifetz Group, and Pat Welsh. Boeglin welcomed both the “financial support and domain expertise.” The pairing is revealing: his public explanation gave experience a place beside money.
Vinny Olmstead of Vocap joined the board alongside Grand Ventures’ Tim Streit. The company’s stated plans included expanding sales resources and strengthening software integrations. These are business-building tasks with separate demands. Selling creates promises; integrations help a product fit into the environment where those promises must be kept. Spending on both suggests how closely growth and implementation were connected in this phase of the company.
March 2022 brought the larger announcement: a $48.5 million Series B from Aldrich Capital Partners. The planned uses included recruitment, sales and marketing, and additional developers. Aldrich joined the board alongside existing investor Vocap. Boeglin’s explanation of the underlying business problem was concise: people had “too much to do and not enough time to do it.” The phrase could hang above a surprising number of office doors.
The progression from a reporting macro to a funded company should not be mistaken for an uninterrupted straight line. These are different projects with different collaborators. What connects them is the operational question they raise: how does work move when the people responsible already have full days? In the financing announcements, Boeglin returned to resources, tools, and the team that would have to turn an expansion plan into regular activity.
“too much to do and not enough time to do it”
Will Boeglin, March 2022
Giving the developers their names
Boeglin’s public updates offer another small window into how he described the work. In 2021, when TimeDoc’s Allscripts integration received recognition, he singled out John-Patrick Di Cosola and the development team. The post discussed a bidirectional integration, a decidedly practical achievement. Such connections let separate systems exchange information; they are also the sort of accomplishment whose difficulty can disappear once they work.
His financing posts likewise put the team in the frame. Announcing the Series A, he welcomed the new investor community. Announcing the Series B, he expressed pride in what the TimeDoc team had accomplished and anticipation about the growth ahead. These are public statements, carefully made for public occasions. Read together, they show whom he chose to name when there was an achievement to announce.
The team photograph suits that record. It places colleagues together behind a company sign, giving an abstract business a collection of faces. A founder’s profile inevitably narrows attention to one person. The picture quietly widens it again. Boeglin’s story includes people who wrote the software, sold it, supported customers, invested, and eventually took responsibility for leading the organization into another phase.
A founder changes chairs
In August 2023, TimeDoc appointed Brian Esterly chief executive. Boeglin stayed on the board and committed to helping the transition. He said he and the board had selected Esterly for his experience. The announcement gives this part of the story a different shape from the fundraising years: the founder was helping choose the person who would take over the executive role.
A handover changes the relationship between a founder and the company’s daily decisions. The board seat preserves a formal connection while another executive takes the operating lead. It also changes how a profile should describe him. “Former CEO” records a substantial chapter. “Board member” identifies his continuing responsibility. Each title says something specific, and neither should be asked to do the other’s work.
Today, TimeDoc lists Boeglin as a co-founder and board member, with Aqil Chishty as CEO. Boeglin also works with Chris Knoff on the non-clinical operations of Signal Internal Medicine in Chicago. His responsibilities there include onboarding, membership questions, scheduling, and logistics. The scale and setting have changed; the job once again includes making the practical arrangements work for the people relying on them.
That is a satisfying place to leave the spreadsheet in view. Boeglin has been a founder seeking capital, a CEO building a team, and a director participating in a company’s continuing life. He is also doing work whose successful outcome may be an appointment arranged or a question answered. An organization needs people willing to attend to those details. They rarely receive the headline. They do, however, have to happen.
Follow the working parts
Company milestones, public profiles, and the people in the story.