My name is Caitlyn, and I am a junior at Skidmore College, double-majoring in Environmental Studies and Management & Business, with a minor in International Affairs. I have spent the past five years working with children and have developed a genuine passion for helping students build confidence in their athletic and academic abilities. Athletically, I offer one-on-one softball coaching for players looking to elevate their skills and deepen their understanding of the game. I am a varsity softball athlete at Skidmore College, playing primarily as a catcher and first baseman. I bring four years of coaching experience, including coaching the Rage Fastpitches 16U team in Massachusetts. I have worked with athletes from 12U to 18U in skill development, strength training, and agility work. As a certified USA Umpire, I also provide a well-rounded understanding of gameplay, strategy, and rules. I am passionate about athlete development and understand firsthand the discipline, mindset, and preparation required to grow both on and off the field. Academically, my primary tutoring focus is English and writing. I believe strong writing skills are foundational to long-term academic success, and I work to help students become clear, confident, and effective communicators. Whether we are working on creative storytelling, reading comprehension, or essay writing, I meet each student where they are and help them grow in a way that builds both skill and self-assurance. I have earned Dean’s List honors multiple semesters at Skidmore and graduated high school with high honors, reflecting my commitment to academic excellence. I am excited to bring my energy, experience, and commitment to growth to the Shires community and look forward to helping students thrive academically and athletically.
Caitlyn works with students from the following schools:
Caitlyn offers in-person tutoring on or near the Skidmore College campus for families across Saratoga Springs New York, Wilton New York, Ballston Spa New York, Greenfield Center New York, Saratoga County New York.
If you have a specific tutor in mind, you're welcome to request them directly — we'll confirm whether they're available and the right fit for your student. Otherwise, Ryan writes a personal email to understand your student's needs, learning style, and goals — then handpicks a tutor from the roster. You're not filling out a form and getting assigned randomly. If the first tutor isn't the right fit after the first session, we'll find you a better match at no extra charge.
Yes. Many families start with a single session to see how the tutor and student connect before committing to a regular schedule. There's no pressure to book in advance — reach out and we'll set something up.
Yes. Many of our tutors are strong across several subjects, and sessions can cover more than one if that's what the student needs that week. Flexibility is built into how we work.
Most of our tutors continue working through breaks, either online or in-person at the college if the tutors remain on campus during that vacation. We'll let you know in advance if a tutor has a gap in availability and arrange coverage with one of our other tutors — in-person or online — in the required subject.
Occasionally, if the student lives very close to the tutor's campus. Most sessions take place on or near the college campus or online. This keeps sessions in an academically focused environment — which tends to produce better results.
The families who see the biggest results are the ones who commit to a regular cadence — typically once, twice, or three times a week. One-on-one tutoring with a student from an elite college, who genuinely understands the material, is a fundamentally different experience from a tutoring center or an app. Most of our clients stay with us for multiple semesters.
Email Ryan@ShiresTutoring.com and mention which tutor and college town you're interested in, or fill out our Request a Tutor form. We typically respond within one business day.
That depends on where your student is starting and how consistently they show up. Caitlyn will identify the specific gaps, focus sessions on them, and adjust as the student progresses. Families who stick to a weekly schedule typically see meaningful progress within four to six weeks.
Email Ryan@ShiresTutoring.com and mention you'd like to work with Caitlyn at Skidmore College, or fill out our Request a Tutor form — you can also click the Request a Tutor button at the bottom of this page. We'll follow up within one business day to confirm availability and schedule your first session.