Daniel Shimmerman Knows the Org Chart Is Only Half the Story

Daniel Shimmerman has a warning for anyone who enjoys a promising sales meeting: check who can actually say yes. Mary may like the product. Mary may love the presentation. Dave may control the budget. An entire year can disappear in the space between those three facts. For a founder who built software to make sales performance more intelligible, it is an appropriately human complication.

Shimmerman, usually known professionally as Dan, co-founded Varicent with Marc Altshuller and served as its original CEO. IBM acquired the Toronto software business in 2012. His career has since taken him through enterprise automation, data storage and, now, a law firm built around AI-assisted work. The businesses differ. Each puts him near an awkward exchange between people, money and systems.

He also hosts a parenting podcast. Its negotiations involve a rather different class of stakeholder. Diapers For Two follows life with a toddler and three adult children, a family arrangement that gives the word “experience” considerable room for interpretation. The executive who has spent years explaining how organizations work has found another subject worth examining: what happens when the people involved have their own ideas.

The commission cheque contains a strategy

Shimmerman came to enterprise software with financial training. He holds an economics degree from York University and an MBA from the University of Toronto, and qualified as a Chartered Accountant. Before Varicent, he worked in enterprise sales at Clarity Systems, selling budgeting software to large companies. That combination matters: he had worked with both the numbers a business promises and the people expected to deliver them.

At Varicent, the territory was incentive compensation. A commission calculation looks tidy when reduced to a percentage. Inside a large sales organization, territories, quotas, different products and different reward structures make the calculation considerably less polite. Someone has to connect the plan to the payment and explain how the result was reached.

Varicent's early proposition extended beyond calculating variable pay. Its software brought together incentive compensation, territory management, quota planning and sales analytics. In 2009, Shimmerman described a market where existing approaches concentrated too narrowly on automating compensation administration. His team's opportunity was to connect those mechanics to business performance.

There is a practical distinction here. Paying a commission accurately solves an immediate problem. Understanding whether that commission encourages the sales a company wants addresses the next one. Shimmerman was selling into the space between the two. The cheque was a piece of strategy that eventually had to survive contact with payroll.

A small starting number, an unusually steep climb

Varicent's growth became visible well beyond its customer meetings. In 2009 it raised $35 million and reported 60 percent revenue growth for the year. A strong fourth quarter brought its highest number of new customer acquisitions to that point. These were results produced during a difficult economic period, when buying enterprise software required a persuasive explanation of what it would change.

The following year's Deloitte Technology Fast 500 table supplied a striking pair of bookends: approximately $62,000 in fiscal 2005 revenue and $25.029 million in fiscal 2009. Deloitte recorded growth of 40,269 percent, placing Varicent sixth overall and first among software companies in that ranking. The tiny starting base belongs beside the impressive percentage; otherwise the number loses its meaning.

By April 2012, Varicent had more than 180 customers. IBM announced an agreement to acquire it and add its compensation and sales performance capabilities to a larger analytics portfolio. The financial terms were undisclosed. The customer list included Hertz, Office Depot, Manpower and Starwood Hotels, names that help explain the appeal: this was software already operating inside organizations with complicated selling arrangements.

For Shimmerman, the acquisition opened a wider distribution channel for the work. The business problem had earned a place inside IBM's analytics strategy. A category that could sound like an administrative corner of finance had become an acquisition target.

Before the spreadsheet, draw the room

The most revealing account of Shimmerman's selling method concerns a mental map. He tries to understand the people involved in a purchase, their preferences and their influence. That map gets revised as the relationship develops. The point is to know whose opinion matters, whose approval is needed and where effort should go.

“It would stink to spend a year trying to sell to Mary only to learn that Dave was the decision maker.”

Dan Shimmerman

The line is funny because the mistake is so ordinary. A seller can mistake enthusiasm for authority. A technically convincing presentation can leave the actual decision untouched. Shimmerman's method adds a social diagram to the financial one: how the organization says it works, and how a purchase really gets made.

It also provides a useful way to read his later career. Enterprise software has to pass between departments that describe the same work differently. Finance sees a cost. Technology sees an integration. A user sees another screen. Knowing the product is only part of the job; knowing how those interests meet can determine whether the product gets used at all.

The next problem was already automated

Shimmerman joined Blueprint Software Systems as CEO in 2014. The company's work would take him into the management and migration of business automations. Organizations had accumulated software bots to carry out repetitive tasks, then faced another problem: what to do when their existing automation platform no longer suited them.

In 2020, Blueprint announced a partnership with Microsoft around Power Automate. In 2021, it expanded the collaboration to help enterprises move portfolios of bots from other platforms to Power Automate Desktop. The proposition addressed a stubborn expense. A company could prefer a new platform while finding that rebuilding all its existing automations made the move hard to justify.

That is a different sales conversation from promising a fresh start. It begins with the work a customer has already paid for. Shimmerman's argument was that switching should become practical, with less manual reconstruction standing between the organization and its preferred tools. The accumulated past, so often omitted from a software demonstration, was part of the product's reason to exist.

Leadership also involved people already inside the company. In 2017, Blueprint promoted four senior leaders into executive roles, including Martin Saipe as chief operating officer and Ruth Zive as chief marketing officer. Shimmerman emphasized the talent developed within the organization. The announcement offers a concrete management detail in a career usually described through products and transactions: advancement could come from the existing team.

By May 2025, he was moderating a Blueprint roundtable on agentic AI with participants from Syncura and Canada Life alongside AI strategist Pramila Nathan. The discussion covered governance and the practical limits of autonomous systems. The subject had moved from bots following instructions to software taking more initiative. Deciding where responsibility sits remained part of the conversation.

Storage, contracts and the price of uncertainty

Another assignment arrived in 2023, when Serene Investment Management acquired Nexsan and appointed Shimmerman CEO. Data storage brought a different set of products and customer obligations. Later that year, Nexsan brought back Victoria Grey and Andy Hill as marketing and sales leaders. The company reported positive operational cash flow and improvements in sales and profitability under its new ownership and leadership.

His latest venture makes the question of responsibility explicit. Ruby lists Shimmerman as co-founder and CEO, alongside Brooke Ash, head of legal, and Irina Lunin, chief technology officer. It is a Canadian corporate-commercial law firm with an operating model built around AI-assisted preparation and human legal review.

The division of work is clear in Ruby's description: AI supports research, drafting and process administration; lawyers apply judgment, advise clients and sign off on the work. This is a business built around a handoff. The quality of that handoff is part of what the client is buying.

Ruby also publishes flat fees. Its current catalog lists agreement drafting from CAD $299 and contract review from CAD $499, with delivery options priced separately. Someone buying a contract can see a starting price before committing. For a founder accustomed to budgeting, the appeal is easy to understand: uncertainty about the bill is itself a business cost.

Read alongside Varicent and Blueprint, Ruby suggests a recurring interest in making complicated transactions easier to understand and manage. That is a reading of the career, rather than a mission statement Shimmerman has supplied. The evidence lies in the successive problems: commissions that need explaining, automations that need moving, contracts that need accountable review.

A different sort of family business

Then there is the podcast. Shimmerman lives in Toronto with his partner Lori. Their family includes three adult children and a young daughter, Ruby. His personal interests include travel and online chess. Neither an IBM acquisition nor a working knowledge of incentive compensation exempts a parent from being surprised at home.

The episode titles show where he looks for stories. Four Kids, Four Menus explores the personalities revealed around the dinner table. Accidental Rituals returns to bedtime inventions and familiar drawings that become family traditions. Daddy's Little Girl, Meet Daddy's Little Girl considers becoming a father to another daughter more than two decades after his first.

These are modest subjects for someone whose professional announcements involve enterprise customers and acquisitions. Their scale is the attraction. A family ritual can matter without becoming more efficient. An ordinary meal can reveal something a carefully arranged conversation misses. There is room in this version of Shimmerman's public life for observation without a business case attached.

His work has repeatedly involved making a process legible enough for someone else to trust it. At home, the stories leave more room for surprise. Mary and Dave still belong on the sales map. The children get a microphone's worth of their own territory.