The Background
Becoming Discoverable in the Age of AI
When a student struggles in the classroom, time matters. A child who is quietly falling behind a reading benchmark, or whose reasoning abilities are going unrecognized, depends on an educator noticing, acting, and getting the right support in place before another school year slips past. Riverside Insights, a U.S. education technology company with nearly a century of experience in assessment development, exists to make that possible. Its portfolio — including CogAT, used to identify student reasoning strengths and guide personalized instruction, and the Woodcock-Johnson assessments, used to evaluate cognitive abilities and pinpoint learning challenges — gives educators the data they need to see each student clearly and respond with precision.
Riverside's mission is to grow the potential in every student. But assessments alone do not move the needle. What moves the needle is an educator who can access results quickly, interpret them confidently, and act on them without waiting days for a support team to call back. When a district administrator or school psychologist reaches out to Riverside with a question, the quality and speed of that response can directly shape how quickly a school responds to a child's needs.
In 2018, Riverside was carved out of HMH and acquired by a private equity firm, setting the company on a course to modernize and grow. The ambition was clear. The infrastructure to support it needed some work.
The Challenge
When the Clock Is Running for a Student, Delays Are Not Neutral
When a school psychologist calls with a question about a clinical assessment protocol, the clock is already running. A student evaluation is underway. A placement decision, an intervention plan, or an IEP accommodation is waiting on the answer. These are not abstract administrative questions. They are the moments where the right information, delivered quickly, can change the path a child is on. Riverside's ability to respond quickly and accurately is not just a customer service standard. It is part of the educational promise the company makes every time an educator chooses one of its tools.
But beneath that promise, the infrastructure was under serious strain.
Shashank Condoor joined Riverside as Sr. Manager of Revenue Operations in early 2024 alongside a new Chief Revenue Officer. What they found was a company that had grown through acquisitions and was running on a patchwork of legacy systems. Sales lived in NetSuite. Marketing was already in HubSpot. Customer service ran through Zendesk and Freshdesk. Reporting happened in Tableau. The space between all of those systems was filled with Excel.
The Hidden Cost of a Fragmented Stack
Not one system spoke to another. Leadership could not get clean answers to basic questions without a team of analysts pulling data from multiple sources and reconciling the differences. The forecasting process had grown unwieldy: a cross-functional team spent the better part of ten days each month building a 50-slide deck, collectively burning more than 450 hours on it.
Riverside also had 55-plus customer service agents managing support volume with no integrated knowledge base, no AI assistance, and no unified view of who was calling and why. When an educator called in, the rep answering had no visibility into that school's history with Riverside, what products they were using, or whether this was a first contact or a recurring issue. Every call started from zero. The team was capable. The tools beneath them were not.
The result: more than $1M annually in technology costs producing data nobody fully trusted, slowing down every team that depended on it.
The Solution
One Platform, One Source of Truth
For educators to get fast, accurate support from Riverside, the teams inside Riverside first needed a unified view of every customer interaction, from the moment a lead entered the system to every service touchpoint that followed. That was the architecture Shashank and the CRO sketched out on a bar napkin at a hotel in Atlanta in early 2024: a single HubSpot environment spanning Sales Hub, Marketing Hub, and Service Hub to replace seven to eight disconnected systems.
Building it was a cross-functional effort from the start. Shashank worked alongside teammates who each brought an important piece of the puzzle: Ally Phelon leading the Customer Agent buildout, Shelby Cronin driving the forecasting transformation, Patrick Nguyen anchoring the Sales Hub implementation, and Lauren Dingus shaping the marketing and sales pipeline workflows. Each of them put their heads together to design a system that would actually work for the people using it every day.
What made it work was adoption. Marketing Hub was already in place. Sales Hub brought pipeline management and field rep workflows into HubSpot, including the mobile app used by reps who spend their days inside school districts, often in buildings with limited connectivity. They upload deal data from whatever network they can find, log activity in the field, and stay current without needing to be back at a desk. Because HubSpot worked for the people actually selling, adoption took hold quickly across the organization. Fast adoption meant clean data, and clean data meant forecasting, reporting, and AI could all function the way they were designed to.
Forecasting in Minutes, Not Days
The forecasting shift was one of the most immediate wins. Collaborating closely with Shelby Cronin, Shashank replaced the 50-slide monthly deck with HubSpot's native forecasting tool, a live view segmented by business unit, seller, and deal priority. Per-person time dropped from 20 to 30 hours per month to 30 to 60 minutes, a 97% reduction. Leadership got what it actually needed: the top 20 deals and visibility into each business unit. The tool did not just save time. It changed how decisions got made.
Scaling Support Without Scaling Headcount
With Service Hub in place and Riverside's knowledge base loaded into HubSpot, Shashank and Ally Phelon deployed Customer Agent to handle a growing share of incoming volume. The results came quickly. Customer Agent took on 35% to 40% of all support requests. Of that, 18% were fully resolved by the agent with no human involvement. Another 17% were resolved through a hybrid model — agent-initiated response with a rep closing the loop on more complex needs.
For Riverside's educators, the shift was immediate and tangible. A school psychologist with a question about assessment scoring no longer waited on hold while a rep searched across disconnected systems for context. A district coordinator troubleshooting access to student results got an answer in the same conversation, not a callback. Common questions were resolved instantly through Customer Agent. More complex ones reached a human rep who already had the full picture. The experience of reaching Riverside changed, and the educators on the other side felt it.
The Transformation
The Educator Experience Comes First
When educators and school districts contact Riverside today, they reach a support operation that is faster and more capable than it was 18 months ago. The school psychologist working through an evaluation no longer waits. The district administrator trying to access results for a student review gets through quickly and leaves with answers. Customer Agent handles more than a third of all incoming support volume, resolving the most common questions instantly, at any hour, without a queue. Riverside's 55-plus customer service agents are freed to focus on the cases that genuinely require expertise: complex clinical questions, nuanced score interpretation, situations where a student's next steps depend on getting it exactly right. For the educators who depend on Riverside, and for the students whose trajectories depend on those educators, that responsiveness is not a feature upgrade. It is a meaningful change in how quickly schools can move.
Internally, the monthly scramble is gone. Riverside now runs forecasting live in HubSpot, and the entire process takes under an hour per person.
A Return That Compounds
Consolidating from more than $1M in annual tech spend to approximately $480K in HubSpot investment produced more than $600K in cost savings. At a private equity-backed company where savings multiply across EBITDA, that return went well beyond face value. And in a year when the education technology industry was in decline, Riverside grew 10%, a result Shashank ties directly to the ease of use HubSpot brought to the sales team. When reps manage pipelines clearly and access customer history from their phones in the field, they sell more.
From Bar Napkin to Business Reality
What Shashank and Riverside's CRO sketched out in Atlanta in early 2024 is now how the company operates. Riverside has end-to-end visibility across the customer lifecycle, from lead to service. As Customer Agent matures, Shashank is focused on making it more robust heading into the back-to-school season, when districts are making decisions and support volume climbs. For a company whose mission is to grow the potential in every student, that momentum is more than an efficiency win. It is what allows Riverside to show up for the educators who depend on it, faster and at a greater scale than before.
"Who would have thought HubSpot could do all of that?" Shashank said. "People thought Excel sheets could do it. Now we have one place that tells us everything, and the business grew because of it."
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