The founding insight arrived as an expensive addition to Deidre Paknad’s week. IBM had acquired PSS Systems, the information-governance company she led, and Paknad was suddenly operating a fast-growing global business inside a vast organization. Her team crossed countries and time zones. The mission mattered. The machinery around the mission kept getting in the way.
Goals sat in PowerPoint. Execution lists lived in spreadsheets. Documents collected in collaboration sites. Email brought everyone else’s urgency to the top of the screen. Paknad estimated that keeping the group aligned added 10 to 12 hours to her week. Those hours went toward restating direction, gathering progress and reconstructing a shared picture that was obsolete almost as soon as it was assembled.
She did not see a motivation problem. She saw a process problem. Managers were responsible for outcomes, yet the ordinary software stack was better at holding documents, tasks and messages than at keeping a team attached to its goals. The gap was so familiar that most companies treated it as management itself.
“I need a faster, better way to lead a team and achieve goals.”Deidre Paknad, recalling the idea behind WorkBoard
Paknad and her co-founder, Daryoush Paknad, began building that faster way. WorkBoard emerged in 2013 and announced its first outside financing in early 2014. The initial product linked goals, priorities, work, feedback and status in one place. It was not pitched as another project tracker. A project has a beginning and an end; a manager keeps running a function, choosing among competing priorities and reporting results upward. WorkBoard was designed around that continuing loop.
Her first product category was corporate memory
WorkBoard was a new company, but the founder’s habit was established much earlier. Paknad has said she loves solving process problems: work that moves too slowly, costs too much or fails to do what it is supposed to do. In her first job after college, she spotted a production issue costing the company $200,000 a month. She devised a fix. The result earned her a promotion and supplied an early proof that a stubborn workflow could be redesigned.
At CoVia Technologies, which she founded and led, her work received Smithsonian recognition for innovation in 1999 and again in 2000. At PSS Systems, she turned toward a particularly unglamorous corporate problem: what companies should preserve, what they could defensibly delete and how to respond when litigation required a legal hold. PSS helped launch commercial applications for legal holds, collections and retention management in 2004. Paknad also founded the Corporate Governance and Oversight Council that year, bringing legal, records and technology practitioners into the same conversation.
The details were technical, but the pattern was plain. Critical knowledge was scattered across systems and departments. Human beings were compensating with meetings, manual checks and institutional memory. PSS made that coordination visible enough to manage. IBM acquired the company in 2010, and Paknad went on to lead IBM’s information lifecycle governance business.
It was an unusually useful vantage point for seeing her next problem. Startups can create alignment through proximity. A few people hear the same customer call, make a choice and change direction before lunch. At IBM’s scale, the message had farther to travel. The work of keeping strategy coherent expanded with every handoff. Paknad knew both speeds: the directness of a startup and the coordination demands of an enterprise.
A strategy needs a rhythm, not a hiding place
The vocabulary around WorkBoard changed as the company matured. Goal management became Objectives and Key Results, or OKRs. The broader system became a “digital operating rhythm.” The phrase captures more than a dashboard. Long-range strategy feeds quarterly objectives. Monthly business reviews test progress. Weekly meetings and one-on-ones surface risk. Each cadence uses the same facts, and each offers a chance to adapt.
The distinction matters because a plan is static while a rhythm is behavioral. A company can buy software and still preserve the old ritual of polishing slides before a review. WorkBoard paired its platform with training and an Outcome Mindset methodology, certifying coaches who could help organizations change the practice around the product. The people layer was part of the implementation, not a concession that the software had failed.
Paknad’s own language returns often to ambition. She argues that teams should imagine their best possible outcomes, organize around them and see how their work contributes. Transparency, in this view, is not surveillance. It is the ability to understand the result and make a better decision without waiting for a chain of status requests.
When a process depends on people repeatedly rebuilding the same picture by hand, make the picture persistent and make the cadence visible.
The market rewarded the thesis. WorkBoard reported tripling sales in 2019 before raising a $30 million Series C led by Andreessen Horowitz in January 2020. A $75 million Series D followed in May 2021. Paknad was named among Goldman Sachs’ 100 Most Intriguing Entrepreneurs in 2019, while WorkBoard later appeared on the Deloitte Technology Fast 500 and the Inc. 5000.
Those milestones describe company velocity. Her more revealing management practice is smaller. As WorkBoard grew, Paknad shared a new “version” of her CEO role at an annual kickoff, including what she would stop, start and keep doing. She has said the exercise was cathartic. It clarified where her involvement would remain predictable and where it should recede. Customer conversations stayed in the mix because they brought her joy and kept her close to the problem.
The software is learning to join the meeting
WorkBoard introduced generative AI across its strategy stack in 2023, then widened the idea from assistance to agency. In February 2025 it announced digital chief-of-staff and leadership-coach agents. Paknad’s framing was characteristically managerial: a small share of leaders can afford a human chief of staff or executive coach, while most managers lack both the capacity and the support. The agents were meant to prepare briefs, spot risks, connect dependencies and offer guidance inside the existing operating rhythm.
The move also sharpened the standard by which the technology should be judged. Companies do not need another machine that produces impressive paragraphs. They need fewer hours spent reconstructing status, earlier warnings when an outcome slips and clearer tradeoffs when priorities collide. The founding complaint remains the test: does the manager get meaningful time back?
In May 2025, WorkBoard acquired Quantive, combining two established names in enterprise OKR software. The acquisition added customers and talent while consolidating a category that had grown crowded. It also arrived alongside partnerships with Microsoft and Workday, embedding the work of goals and strategy into systems employees already use.
“Our AI agents radically accelerate strategy adaptation and execution.”Deidre Paknad, on the Quantive acquisition
By June 2026 the platform had pushed into strategic portfolio management with a Portfolio Analyst agent. The new product connected strategy and OKRs to initiatives, investment choices, projects and people. Here again, Paknad aimed at a process whose incumbents had become heavy with training, reporting and specialist labor. The interface moved toward conversation; the underlying promise stayed outcome-centric.
A career built in the gaps
There is a neat symmetry between Paknad’s two major software chapters. Information governance asks what an organization knows, where that knowledge sits and what must happen to it. Strategy execution asks what an organization wants, how the work connects and whether the result is arriving. Both problems live between departments. Both become dangerous when ownership is fuzzy. Both invite layers of compensating administration.
Paknad’s answer has been to turn those gaps into systems. She holds more than a dozen patents, speaks regularly about outcome mindset and hosts The OKR Podcast, where conversations with executives make the operating craft public. The aspiration is larger than making OKRs easier to update. It is to make strategy a shared, current fact rather than a message that degrades as it moves through the company.
Her public voice has room for candor outside the operating model. At the start of 2026, she wrote about taking two weeks fully away from LinkedIn, Slack, Teams and her laptop, choosing family, travel, novels and sleep instead. The pause reads less like an exception to her focus on outcomes than a practical boundary around it. Even a carefully designed rhythm needs a rest.
WorkBoard is now a larger platform than the app Paknad once wished she had at IBM. It spans strategy, goals, reviews, coaching, agents and portfolios. Yet its central question has barely moved: how can a leader keep ambition visible while an organization gets noisy? Paknad found a company in the hours that question consumed. She is still redesigning the answer.