Jacob Singer

Connecticut Based Pilot and Flight Instructor

About Me:

My name's Jacob, originally from St. Thomas in the US Virgin Islands. My journey in aviation started at age 12 with my discovery flight. I soloed at age 16, achieved my private pilot certificate at 17, and became and started working as a certified flight instructor at age 18. To say aviation is a huge part of my life is a massive understatement!

I've made it a point to learn and experience as much as I possibly can in aviation, and I'd love to help pass on the knowledge and techniques I've picked up over the 8+ years I've been flying.

I currently am able to provide training in your airplane within an hour of Hartford, or through the Oxford Flying Club based at the Waterbury-Oxford Airport (KOXC).

Flight Instruction Services

  • Learning to fly is one of the most rewarding challenges out there, and I love helping new students build a strong foundation from day one. Whether you're just starting your aviation journey or deep into your private pilot training, I’ll work with you at your pace to make sure you’re confident, safe, and having fun while learning the essentials.

  • Instrument flying completely changes the way you see aviation, and it’s one of my favorite things to teach. From flying approaches in real IMC to managing real-world IFR scenarios, I’ll help you understand and apply the skills you need to fly with precision and confidence, whether that’s in a classic six pack or a technically advanced airplane.

  • Commercial training is where everything starts to come together. It’s about sharpening your skills, flying with more precision, and learning how to think and operate like a professional pilot. We’ll focus on flying smooth, consistent maneuvers, refining your decision-making, and developing the kind of confidence and polish that sets you apart, whether you're planning a career in aviation or just want to take your flying to the next level.

  • Flying a twin is exciting, but it comes with real responsibility. With the added performance comes added complexity, and mishandling a multi-engine airplane, especially in an engine-out scenario, can be unforgiving. I focus on helping you truly understand the “why” behind the procedures so you can handle the aircraft confidently and safely.

  • Becoming a CFI is one of the most challenging and rewarding steps in aviation. Whether you're working on your initial CFI certificate, or adding on instrument or airplane class privileges, I’ll help you break down complex topics, build lessons that actually make sense, and teach in a way that’s clear and effective. We’ll go beyond just memorizing acronyms and dive into how to actually connect with students and pass on the skills you’ve built. My goal is to make sure you walk into your checkride, and your first student flight, ready to lead with confidence.

  • A flight review should be more than a quick refresher, it’s a chance to fly with purpose and sharpen the skills that matter most. I tailor each session to your experience and the type of flying you do, focusing on real-world scenarios, sound decision-making, and practical proficiency. You’ll leave with more than just a sign-off, you’ll leave more confident and more prepared.

  • If you’re getting back into IFR flying, an IPC is the perfect time to focus on what really matters. I don’t just run through the motions, I build each session around practical skills that make you sharper in the system. We’ll work through realistic scenarios that build real confidence, not just currency.

  • Learning a new aircraft should feel smooth and manageable, not overwhelming. I bring experience flying a variety of general aviation aircraft, from steam gauge trainers to complex, high-performance, and technically advanced platforms. That perspective helps me guide you through the systems, avionics, and handling characteristics in a way that makes sense. The goal is to help you build confidence, understand the airplane, and fly it safely and efficiently.

Let’s Work Together

Interested in working together? Fill out some info and I will be in touch shortly! I can't wait to hear from you!