Most executives keep a careful account of their successes. Steve Taplin has given the failures unusually good billing. Thirty ventures, by his own count. Twenty that failed. Ten that succeeded. The arithmetic sits near the front of his public story, where a more cautious biography might put an award. Failure, apparently, has finally secured a place above the fold.
Taplin is the co-founder and CEO of Sonatafy Technology, based in Scottsdale, Arizona. He writes books, interviews technology leaders and works on a problem that will be familiar to anyone who has attended a software status meeting: an organization can employ capable people, keep them thoroughly occupied and still struggle to deliver the thing it promised.
His interest has a long apprenticeship behind it. There is IBM, there is an MBA completed while working, and there is a stretch of entrepreneurial life that includes property businesses as well as technology. His story has detours. He has decided they belong in the telling.
A self-reported career tally, not audited investment returns. Each segment represents one venture.
Before the cloud had its present name
Taplin describes himself as originally from Chicago. In one conversation about nearshore software development, the Bears jersey behind him provided a small geographic footnote. He now lives in Scottsdale, but the professional beginning he recalls is in Schaumburg, Illinois, at IBM’s early e-business hosting center.
This was the period when businesses were learning to put serious operations on the internet. Taplin remembers working around what would later be recognized as cloud data-center infrastructure, then moving into sales of complex outsourcing arrangements. The vocabulary has since become more elegant. The underlying requirement remains rather stubborn: somebody has to make the system work.
His education paired a bachelor’s degree in Management Information Systems at Northern Illinois University with an MBA at DePaul’s Kellstadt business school. He completed the MBA between 2000 and 2002 while working at IBM. That combination put business study alongside the daily task of selling technology to organizations with actual budgets and actual objections.
The next chapter resists a tidy software-industry narrative. His older career writing describes real estate investment, brokerage and mortgage businesses dating from 2002. It also records his leadership of Diversified Residential between 2012 and 2015. Software remained part of the work: he described building systems to organize property acquisition and management. A building and a software release have different delivery problems, but neither can be rescued indefinitely by a handsome presentation.
A shared working day
Corporate technology returned to the story. Before Sonatafy, Taplin was a vice president in strategic pursuits at DXC Technology. By July 2020, he was Sonatafy’s CEO and a board member. The company describes its formation that year through acquisition, building on an engineering organization established in 2005. Those dates explain why the business has both an older engineering history and a newer corporate chapter.
The central commercial idea is straightforward. U.S. businesses need software engineers. Latin America has engineers whose working hours can overlap with those of their clients. Sonatafy organizes that relationship, combining U.S. leadership with engineering teams across the region. A shared working day gives questions a chance to receive answers before everybody goes home.
Taplin was discussing the model publicly well before the current wave of AI enthusiasm. In February 2022, he described a U.S.-headquartered business with remote developers in Mexico and plans to expand across Latin America. He was seeking growth capital for an operating business. Recurring client work and longer engagements were central to the proposition.
His involvement also reached the international services conversation. He was listed on the September 2021 programme for UNCTAD’s Global Services Forum, on a panel about nearshoring opportunities. The subject connected his company’s immediate work to a broader question: where should services be delivered when geography no longer requires everyone to occupy the same building?
A schematic of the model, not a project schedule.
There is external recognition to place beside the company’s own account. Sonatafy appeared at No. 1,273 on the 2024 Inc. 5000 and No. 3,912 in 2025. The rankings describe the company’s presence on those annual lists. They also mark a practical change in scale from the early capital-raising conversations.
Taplin’s attention now falls particularly on responsibility for delivery. Sonatafy describes managed teams that pair a U.S. principal engineer with senior Latin American engineers. The proposed benefit is clearer ownership of what gets built. In his version of the problem, adding capable people cannot compensate forever for uncertainty about who must make the final decision.
The door was part of the meeting
One story Taplin tells about leadership takes place in a client meeting that went badly before it went better. He recalls arriving with a team of fifteen to repair a relationship with a Fortune 500 retailer. The CIO came late and behaved with hostility. After repeatedly requesting professional conduct, Taplin says he stood up and led his team out.
In his account, the CIO followed them down the hall and asked them to return. They did, and the relationship was repaired. The detail that matters is the walk. For a moment, preserving the meeting ceased to be the most important job in the room.
Taplin has also described changing his priorities from financial measures alone toward team culture. Taken together, these accounts give his leadership language a specific test: what treatment will an executive accept when a client relationship is at stake? An organization learns something about its values when keeping the appointment becomes less important than keeping faith with the people who attended it.
His writing offers a quieter version of the same concern. In a 2023 essay, he argued that executives should spend time alongside employees to understand how work actually happens. Distance gives senior people a convenient view. It can also edit out the inconvenient parts.
That essay recommends direct contact with everyday operations as a way to understand customers, identify problems and build accountability. It is easy to see the appeal for someone whose career began around infrastructure and moved through sales. A problem described in a boardroom may look considerably different to the person who has to fix it before the afternoon ends.
Another essay makes the case for giving employees more control. Taplin argues for trust, access to information and a clear understanding of success. These ideas require a leader to tolerate questions and let capable people try things. The manager who supplies every answer may eventually discover that answering has become their entire occupation.
There is a useful tension here. He wants leaders close enough to understand the work, and employees free enough to perform it. Both positions require judgment. Staying involved can become hovering; delegation can become abandonment. His published argument asks the executive to keep paying attention without occupying every available inch of the room.
Busy has a very good publicist
Taplin’s recent vocabulary gives names to familiar office frustrations. He talks about an ownership gap, the cost of coordination and the misleading comfort of a full backlog. The shared concern is that visible activity can obscure the harder question of whether useful software is reaching its intended users.
That concern became a book with Sonatafy CTO Chris Horvat: The Backlog Illusion. Its subject is the software organization that looks productive while delivery slows. His earlier book, Fail Hard, Win Big, takes the broader entrepreneurial record as its material. One looks at the accumulated work; the other at the accumulated attempts.
“20 failures taught more than 10 successes ever could.”
Steve Taplin
He also makes room for other people’s operating histories. Software Leaders Uncensored brings CTOs, founders and engineering leaders into conversations about their careers and decisions. Sonatafy’s podcast page now lists more than 215 episodes. For a founder with plenty of his own material, hosting creates an opportunity to listen.
The guests make the range concrete. Jim Olsen discussed a career that moved through programming, open-source work and technology leadership. Jimi Li described the path from engineering to CTO work across several industries. The conversations give Taplin access to different versions of problems he meets in his own business: how teams grow, how decisions change and what executives learn after taking responsibility.
There is a practical connection between that interviewing and his work. A person selling help with software delivery benefits from understanding what engineering leaders are actually struggling with. The show gives those leaders time to explain, with the career behind the answer still attached.
The next attempt still needs a customer
In a March 2026 leadership conversation, Taplin discussed learning from failure, journaling and deciding when to persist or stop. One of his blunt observations begins: “Nobody cares about your business.” The customer’s interest, he explains, is in the problem the business solves. Founders can become very attached to the noun. Customers tend to inquire about the verb.
His public life now includes books, a newsletter called The Tech Dilemma, speaking engagements and regular writing. Those are several ways of returning to the same practical questions. How do people organize work? How do they recover from a wrong decision? How do they know when an enterprise deserves another attempt?
Beyond work, his interviews describe hiking, travel, time with family and his dogs. The Chicago connection survives in that Bears jersey. These are small details, but they let a person back into a career crowded with companies, job titles and delivery frameworks.
The appeal of Taplin’s story lies in the incomplete scorecard he is willing to display. Ten wins sit beside twenty failures. An IBM beginning sits beside entrepreneurial detours. Today’s books and interviews sit beside the daily obligation of running Sonatafy. There is always another conversation to have, another decision to make and, eventually, some software that has to leave the meeting.