Ryan Winter and the Trouble with a Perfectly Good Chart

When Jayme Orlando needed to understand what was happening at her school, Ryan Winter helped her read the reports. Orlando, principal of Clark Mills in New Jersey’s Manalapan-Englishtown district, was learning to work with LinkIt!, the education software company he leads. She wanted to become proficient enough to bring the knowledge back to her teachers. Winter worked with her on interpreting the information and understanding the application. A company president had found himself doing something rather close to teaching.

The detail is small enough to miss in a career that includes Princeton, investment banking and a growth investment. It is also a useful place to begin. A report can arrive complete, correct and attractively arranged while leaving its reader with a perfectly reasonable question: what am I supposed to do now?

Winter’s work sits beside that question. As LinkIt!’s co-founder, CEO and president, he has a business to grow. His customers have schools to run. The distance between those two obligations is where much of his story takes place.

The principal and the report

At Clark Mills, Orlando was confronting disappointing achievement results. She already cared about school culture. The challenge was turning that care into a more precise understanding of what students needed to learn. Historical results, reading assessments and benchmarks could help, provided the adults knew how to examine them together.

Winter helped her develop that understanding. Orlando then held data meetings with teachers, looking across several kinds of evidence and breaking the results down by skills and standards. The school’s work required teachers to learn the system and reconsider parts of their instruction. The improvement belonged to the educators and students doing that work; Winter’s part was helping a school leader become more capable of leading it.

That distinction gives the episode its interest. A useful explanation can travel. Orlando could take what she learned into a faculty meeting, where colleagues could apply it to their own students. The relationship extended beyond a demonstration of features. It put understanding into circulation.

“It requires people working with one another to achieve a common goal.”

Ryan Winter

There is a certain appeal to selling software that explains itself. Institutional software tends to meet institutions, which have their own plans. People bring established routines, different levels of confidence and a full day’s work. A login arrives more quickly than a shared habit.

An analyst changes his audience

Winter studied economics at Princeton, attending from 1996 to 2000. Before LinkIt!, his career included investment banking at HSBC and Credit Suisse’s Technology Group, followed by senior investment analyst roles at Knowledge Investment Partners and Rudman Capital. His investing work covered education, software and technology businesses.

Those jobs placed him on the side of the table where a business becomes something to evaluate. At LinkIt!, he became responsible for operating one. It is an interesting change of audience for someone working with numbers: from examining companies to helping educators examine their own evidence.

The continuity is visible without assigning him a convenient conversion story. Analysis mattered in the earlier career. It matters in the present one. The practical question changed. A school leader needs to understand what an assessment says about a group of learners, then work with colleagues on an instructional response.

His interest in how information reaches its reader also appears in a quieter credential. In 2016, Jenny Grant Rankin listed him among the contributors of vignettes to How to Make Data Reports that Work. The book addresses the design of reports and systems used by educators. Report design sounds like a specialist concern until someone has to make a consequential decision from a confusing display.

The reader’s effort belongs in the calculation. A graph may be easy for its designer to explain and difficult for everyone else to interpret. Helping a principal understand a report and contributing to a book about reports occupy neighboring territory: both take the recipient’s understanding seriously.

Bring your own pumpkins

Then there is the workshop with the Halloween stationery. Winter co-facilitated a BLaST IU 17 professional-learning event where educators circulated among posted data displays, discussed their observations and marked them with themed sticky notes. Pumpkins, bats, ghosts and cats had acquired an administrative purpose.

The exercises moved from regional assessment information toward district, building and anonymized student data. Winter led work examining skills and standards and demonstrated grouping features teachers could use for differentiated instruction. The workshop gave participants something to inspect, something to discuss and information connected to their own schools.

Halloween usually asks adults to pretend to be somebody else. Here, the point was to help them do their actual jobs. Moving around a room offered occasions to compare interpretations. A colleague’s observation could make a pattern easier to see. The sticky notes gave the discussion somewhere to land.

For Winter’s story, the important feature is his presence in the exercise. An executive whose responsibilities include growth was working through educational evidence with the people expected to use the product. The activity made the company’s support philosophy tangible, down to the office supplies.

His public conversations follow that practical interest. In December 2023, he joined Donna Gaffney, Rebecca Millspaugh and Brandon Langer on The MCIULearns Podcast to discuss multi-tiered systems of support and school data platforms. MTSS is the educational framework for organizing different levels of support around students’ needs. The episode’s focus was implementation and decision-making, the work required to get a framework into use.

Choosing who gets a seat at the table

A company built around close working relationships eventually faces a question of its own: how to grow them. In December 2022, LinkIt! announced an investment from Serent Capital. The plans included geographic expansion, product development and further integrations. Winter emphasized the time spent choosing a partner and the importance of preserving the company’s approach to client support.

The partnership also brought another experienced education entrepreneur closer. Lane Rankin, founder of Data Director and Illuminate Education, was joining LinkIt!’s board. Co-founder and executive chairman Josh Powe welcomed a former competitor as a colleague and adviser. A growing company’s table can become an interesting place when the seating plan changes.

Winter’s own advice to founders, published in Serent’s 2023 review, combined trust in one’s judgment with a willingness to seek expertise. He urged founders to remain open to growth and change and to use their partner’s resources where their own expertise or capacity was limited. There is room in that position for conviction and for asking a better-informed person.

In January 2026, another relationship became part of the company. Winter announced the acquisition of Magnolia Consulting Group, whose team had worked alongside LinkIt! for years. Magnolia became a consulting division, adding instructional expertise and professional learning to the business. Winter connected the decision to helping districts with implementation, student support and leadership development.

That move gives an organizational form to the earlier school story. Hiring software and changing a working practice are related purchases. Putting consulting beside the platform brings the people who help with the practice closer to the people who build the tools.

In June 2026, LinkIt! also acquired Plan Forward, a K-12 survey and analytics business founded by Anne Spear. She was joining full-time to lead surveys and qualitative products and develop Survey Studio. The addition widened the kinds of evidence available to the company’s district customers. Scores can show one part of a school’s experience; well-designed surveys can ask people about another.

For an executive accustomed to assessment data, adding surveys introduces another kind of conversation. A response can contain a judgment, an experience or a question that a score does not capture. The acquisition makes room for that evidence in the same business. Its usefulness will still depend on how clearly schools can interpret what people say and connect it to decisions.

The next person has to understand it

Winter’s public anniversary reflection offers a less formal view of the enterprise. Marking 17 years of leading and growing LinkIt! in 2025, he thanked clients, colleagues, friends, family, Serent Capital and his wife. He credited customers’ feedback and trust, and his colleagues’ commitment to the work. The message put a long business tenure into the language of relationships.

He continues to have the broad obligations of an executive. Growth brings decisions about products, staffing, partners and markets. Staying close to customers does not remove those decisions. It supplies occasions to test them against what a school is actually trying to accomplish.

The principal learning a report, the educators comparing observations and the consulting team joining the company belong to the same working problem. Information needs an audience that can use it. Winter’s career has brought him repeatedly to that audience, where an explanation has to survive questions and a product has to fit into a busy day.

Return to Orlando passing her new knowledge to her teachers. The president’s explanation has left the conversation and entered somebody else’s work. A chart can remain on a screen indefinitely. This is the more interesting journey: one person understands enough to help the next.