Cheshire School District, located in central Connecticut, serves just over 4,300 students across 13 school sites. The district is known for its long-standing tradition of pairing strong academic programs with a forward-looking vision for student success. This commitment is reflected in its mission statement which pledges to “prepare all students to meet the challenges of an ever-changing global society by providing high quality educational opportunities that inspire lifelong learning and service to others.”

At Cheshire High School (CHS), Director of School Counseling, Michelle Boss, leads a team of eight counselors dedicated to bringing this goal to life. To accomplish this work, six counselors support CHS’s 1,200 students across grades 9-12, while one works full-time in the school’s College and Career Center. For many years, the district’s college and career readiness work primarily focused on supporting students pursuing traditional four-year college pathways with the vast majority–historically, between 80% and 90%--of each graduating class following this route. This, however, has begun to change.

More Students Focused on Career Pathways

In recent years, Boss and her team have observed a notable shift in the postsecondary aspirations of their students: an increasing number are exploring two-year programs, trade and technical pathways, or choosing to enter the workforce directly after graduation. This evolving landscape has required the counseling department to adapt both its approach and the tools it uses to support students. Boss emphasized that counselors have had to broaden their knowledge and skillsets to ensure they can meet the needs of every student regardless of which postsecondary path they choose.

Implementing SchooLinks has been a key part of this effort. Boss explained that “So many of the postsecondary systems that are out there are really geared towards four-year students. SchooLinks is breaking that norm and providing more quality information to students who are going to all different pathways after high school.” Boss shared that with SchooLinks, Cheshire students are able to explore their career options more thoroughly while still in high school and make intentional decisions that align with their goals. This includes mapping out coursework to support future career interests and taking advantage of career-centered learning opportunities integrated into the high school experience. The platform ensures that students can see how each choice they make–whether a class, credential, or experience–can help nurture their long-term pathway.

SchooLinks has strengthened Cheshire’s overall capacity for career exploration and industry connections. Boss highlighted the platform’s career search feature, which gives students access to videos of professionals in the field and opportunities to ask them questions directly. These interactive elements have resonated strongly with students, who appreciate seeing contemporary, real-world examples of career paths presented in formats that feel natural and engaging. Boss explained that when these quick snapshots spark interest, students can then use SchooLinks to dive deeper–exploring specific career options and the types of training or education required to pursue them. She and her team are excited to continue building on this feature to further expand connections between career exploration and local industry partners.

Empowering College-Bound Students to Find the Best Fit

SchooLinks has also been instrumental in supporting Cheshire’s college-bound students by giving them powerful tools to explore postsecondary options, manage the application process, and make informed decisions. On average, Cheshire students submit about five college applications each. While SchooLinks has not necessarily changed the number of schools students apply to, it has transformed how they build their lists.

Boss explained that it is best practice for students to apply to a balanced mix of target, reach, and safety schools. In the past, determining which schools fit into each category was often challenging and required significant counselor oversight. Boss shared that

“With SchooLinks, students are able to gauge that on their own rather than their counselor making those categories for them.”

SchooLinks has empowered students to take greater ownership of this process by utilizing the platform’s data and exploration tools to evaluate their options and categorize schools more accurately. 

Students have embraced this independence, finding the platform intuitive and appreciating how easy it is to navigate. They especially value the scattergram feature, which allows them to use both national and district data to understand where they stand academically when deciding where to apply. This blend of data visualization and personalized exploration allows students to create application lists that align more closely with their academic profiles, financial considerations, and personal goals–ultimately helping them identify the schools that are the best fit for them and their future.

Ensuring Every Student Has a Strong Resume

One of the most impactful ways Cheshire High School is utilizing SchooLinks is through its resume-building tool, which has quickly become a core part of students’ college and career readiness journey. An incredible 80 percent of seniors are now using SchooLinks to create and update their resumes. Boss described this feature as “one of the most impressive” elements the district evaluated when selecting a new platform. Boss explained that their previous CCR system had a resume builder, but functionality was so limited that very few students saw value in using it. SchooLinks, on the other hand, has transformed the process, providing students with a seamless and guided experience.

Boss described that the platform clearly walks students through the key elements of a professional resume, prompting them to include appropriate and relevant information. Once students have entered their experiences, their resumes can be easily downloaded into both Google and Microsoft formats, allowing them to make edits depending on the use case. This accessibility has made resume-building practical and meaningful for students. Cheshire begins this work early in a student’s high school career, introducing all freshmen to the SchooLinks resume builder and prompting them to start with basic information such as name, clubs, and activities. They are then encouraged to revisit and update their resumes each year so that, by senior year, their materials are comprehensive and polished.

The effort extends beyond the counseling department. Cheshire’s business department has fully integrated SchooLinks and the resume builder into its curriculum, using it in the required personal finance course and across business classes. This whole-school approach reinforces the importance of resume-building as a skill that develops over time. Boss shared that this has led to students logging into the platform and updating their resumes on their own, without any reminders–an important marker of success for the counseling team. She described cultivating student initiative in the college and career readiness process as a primary goal of her work, and noted that with SchooLinks, students are increasingly taking ownership of their future in powerful ways. 

Unmatched Quality of Customer Support

For Boss, one of the most exceptional aspects of SchooLinks has been the quality of its customer service and support, which she described as “outstanding.” She has been particularly impressed by having a dedicated SchooLinks support representative who works directly with her school. Boss emphasized the SchooLinks team’s remarkable responsiveness, noting that questions or issues are typically answered within minutes and always within the same business day. Just as importantly, responses are thorough and solution-oriented–whether that means resolving the problem, providing a clear and detailed answer, or outlining the steps being taken if additional work is required.

Boss reflected that this level of service and care “makes a difference every day” for her counselors and students. She noted how rare and valuable this kind of collaboration is, contrasting it with past experiences with other companies where problems often lingered for months without resolution. She explained that most interactions with SchooLinks are not about fixing problems but about learning how to maximize the platform’s capabilities for Cheshire’s unique needs. This ongoing relationship with their dedicated representative has allowed SchooLinks to adapt and tailor elements of the platform, ensuring that the system works for the district–not the other way around. Boss noted that this thoughtful, collaborative approach has supported “the needs of all stakeholders,” reflecting a true partnership that strengthens their work with students every day.

This level of support helped set the stage for an exceptionally smooth implementation. Counselors have appreciated the expanded functionality and analytic tools, while teachers found the new system easier to use. “Change is hard,” Boss said,

“but the feedback we received early on was that SchooLinks was much easier than our previous system.”

The data transfer process was similarly seamless. SchooLinks coordinated closely with the district IT department to ensure that all historical data migrated smoothly, with nothing lost in the transition. Boss noted that this was a significant point of reassurance for the entire community.

Laying a Districtwide Foundation for Student CCR Success

For Cheshire, SchooLinks has done more than support individual students in their postsecondary planning–it has helped lay a strong, districtwide foundation for college and career readiness. The district has extended SchooLinks into elementary and middle schools, ensuring students begin exploring career pathways and building skills early. By utilizing SchooLinks’ clear scope and sequence across grades 6-12, Cheshire has created a thoughtful and intentional approach to CCR planning. Boss emphasized that this structure allows the district to strategically scaffold student experiences year over year, so that by the time students graduate, they have fully utilized SchooLinks’ capabilities to explore careers, plan coursework, and prepare for life after high school. 

Boss shared that a guiding principle for her work is, “Do what is best for your students!” For Cheshire, that meant embracing a platform that could meet the breadth and depth of students’ evolving needs. At the time of their decision, no other districts in Connecticut were using SchooLinks. Boss evaluated multiple systems, and during the vetting process, she recalled thinking that everything the SchooLinks team described “sounded too good to be true” because it so closely aligned with the vision she and her team had for supporting students. 

When asked what advice she had for other districts, Boss was clear and passionate: “If you find something that is right for your students, then fight to get that software and that capability in your district.” Boss did just that, and the results have been transformative. Today, SchooLinks is used widely across Connecticut–a testament to the value it delivers to students, educators, and communities.

‍