H.O. Penn Machinery Co. is the Caterpillar® dealer for Metro New York and Connecticut and has been dedicated to outstanding customer service for more than 100 years. We sell and service Caterpillar’s full line of Construction Equipment, Paving Equipment, Generators, Industrial Engines, and Truck and Marine Engines.

For information about internships or job opportunities, please contact Jessica Loeffler by emailing

Call 855-CAT-4-JOB for any inquiries regarding any open positions we currently have. 

View Our Open Positions

We have over 400 employees working in our five branch locations:

  • Poughkeepsie, NY
  • Bloomingburg, NY
  • Bronx, NY
  • Holtsville, NY (on Long Island)
  • Newington, CT
  • Medford, NY

Our Benefits

Our vision is to be a high performing company with the goal of being the recognized leader in every industry we serve. We are committed to living by our values: Ethical, Success, Innovation, Quality and Communication and finding “All-Win” solutions for all of our stakeholders. It is the Managing By Values® Process that differentiates H.O. Penn.

H.O. Penn offers highly attractive compensation with outstanding benefits.

Talent Development

Whether you are someone who aspires to be a leader, technician, salesperson, or want to work in an operations role, there is a focus on the opportunity for growth at H.O. Penn. Available tools and resources range from Caterpillar Certifications to web based and live training to one on one coaching sessions with a trained professional to help identify opportunities for development.


The wellbeing of you and your family is important to us. For all non-union positions, we offer a comprehensive benefits package for our employees, including: medical, dental, vision, 401K, accident coverage, hospital indemnity, group specified disease plan, life insurance, flexible spending account, health savings account, disability coverage, Employee Assistance Program, paid time off, and paid holidays.

Union Benefits

For all union positions, in addition to contributions to your pension, annuity and welfare funds,
your medical benefits would be provided by the union and are best in industry. We also offer all
of our voluntary benefits to union members, such as: accident coverage, hospital indemnity, and
group specified disease plan. Holidays and paid time off are determined by your collective
bargaining agreement.

What Else Sets Us Apart

We operate using two systematic methods: Working by Values and Managing by Values. MBV
and WBV helps H.O. Penn identify and commit to a common purpose and shared values.
Additionally, we are a family-oriented company that has been in business for 100 years. When
you work at H.O. Penn, you join a family that is dedicated and committed to each other and our

Wellness Program

Annual Wellness Fairs, quarterly Get Active Wellness Challenges, on-site Biometrics and Flu
Shots, monthly wellness offerings including webinars and seminars, virtual nutrition counseling,
and more! H.O. Penn values the health and wellbeing of our employees and their families.

Technical Tuition Repayment Program

We help you take control of your student debt! For all Mechanic employees, if you have student
debt for obtaining your technical knowledge, we make an extra payment each month on your
behalf to the financial institution. This reduces what you pay in interest, and allows you to pay
off your loan sooner by shrinking your balance faster.

Technical Training

With a dedicated Technical Training Manager, Technical Trainers, and Technical
Communicators – H.O. Penn offers best in class training to all mechanics to keep up with our
customer needs and focus on your development and growth as a Caterpillar Mechanic.

Types of Careers at H.O. Penn

With six locations across New York and Connecticut, we offer a variety of positions, which include the following areas:

  • Construction Equipment & Generator Service
  • Sales
  • Finance, Accounting & Credit
  • Product Support
  • Human Resources & Training
  • Marketing

Our team members also specialize in several areas, including rentals, parts and more.

The Values of H.O. Penn Machinery

At H.O. Penn, it’s vital that our family of employees share in our defining values, which include:

  • Ethical: Our staff is fair, honest and accountable. We always do what’s right, building long-term relationships with companies throughout our local community.
  • Success: Like Caterpillar employees, we look for ways to best use our time and resources, as well as how to improve ourselves to serve our clients better.
  • Innovation: We promote forward-thinking. It lets us offer innovative solutions to customers, plus pushes the value we provide to companies forward.
  • Quality: For all jobs at H.O. Penn, there is a commitment to exceptional performance, exceeding expectations and excelling when it comes to professional growth.
  • Communication: We support a positive, all-win work environment that emphasizes respect and courtesy, as well as going the extra mile to achieve goals.

With our values, we continue to help our customers build a better tomorrow at H.O. Penn Machinery.

Sean Kimbark
Class A Shop Mechanic, Poughkeepsie NY

“I have been with H.O Penn for about 5 years, joining shortly after graduating from SUNY Cobleskill’s Agricultural Equipment Technology program. Before Cobleskill, I worked at Durant’s Tool Rental, maintaining and repairing a wide variety of equipment. 
I started at H.O. Penn Machinery as a Class C mechanic. My first job was working on a 988F Certified Rebuild with one of the Class A mechanics. I was quickly humbled by the amount of experience and knowledge these guys had compared to me, but that quickly changed. Everybody was very willing to help me learn, and I did. About a year later I was promoted to Class B, and then Class A another year after that. I’m now finding myself in the shoes of the mechanic I worked with when I first started, working on high-profile jobs, sharing my knowledge with others—and still learning, myself. The best thing about working here is the opportunity to hone your skills and learn new things about a very wide variety of equipment. Everyday poses a new challenge but the feeling of accomplishment after completion is unrivaled. If you’re thinking about working at H.O Penn, know this: it can be a challenging job, but it’s also a rewarding job. Nothing beats the feeling of watching a massive machine you just had torn down to the frame drive out of the shop. You’ll learn new things every day, your skills will grow exponentially, and you’ll be proud to tell people what you do.”

Steven Skeen
Technical Communicator, Bronx NY

“During my orientation at Penn College, it was mentioned that there are several dealers that are a part of the Heavy Equipment (CAT Emphasis) program, H.O. PENN being one of them. I contacted H.O. PENN to see if they would sponsor me as a student and help guide me toward future employment. H.O. PENN allowed me to start prior to attending college to help point me in the right direction. They provided me with tuition assistance, internships, and other work opportunities when I was not attending class. After obtaining my degrees, H.O. PENN immediately had a job waiting for me and I began my career as a Technician. This led to becoming a Field Service Supervisor and eventually landing my dream job as a Technical Communicator. You can go just about anywhere to make a dollar in life, but rarely do you find a company with the same like-minded individuals, that will go out of their way to ask you what your career goals are, and then do everything in their power to get you there. This is my career, this is my family, this is H.O.PENN.”

Wade Burton
Class A Mechanic, Newington CT

“As far as I can remember, I have always loved the sound of a diesel engine. After completing my high school senior year project on diesel technology, I was hooked. The following year I attended Pennsylvania College of Technology to pursue an associate’s degree as a heavy equipment technician, where I also partnered with H.O. Penn Machinery as a sponsor. After my first year at Penn tech, I developed a strong foundation and was ready to start my internship at H.O. Penn Machinery. During the time spent as an intern, I used my newly found skills and put them to work. I started by accompanying some senior technicians and learned as much as possible. Gradually, I transitioned to completing jobs independently after proving myself. Fast forwarding three years after graduating, I was promoted to a class 1 technician, responsible for completing the same caliber of jobs as the senior technicians. While being a technician at H.O. Penn, I’ve realized that we support many fields besides construction equipment. Some of the fields included are mining, power generation, marine diesel, land and waste management, as well as paving. The two leading reasons why I chose to pursue a career as a technician at H.O. Penn are; the team of employees across the departments and the resources they can provide to help you grow, as well as the opportunity given by the company to pursue the multiple facets within this industry.”

The Managing By Values® Approach

Our dedication to our customers is why we’ve adopted the Managing By Values® approach, which consists of three overarching steps:

  • Define values that coordinate with mission and vision.
  • Communicate defined values to the entire organization.
  • Align defined values to work practices.

In the more than 20 years since introducing Managing By Values®, we noticed significant gains in our performance and service, as well as employee offerings.

Search for H.O. Penn Jobs Near You

At H.O. Penn, we’re a company that means what we say — we believe in our values, and we embody them every day as we assist customers and each other. When you become a part of our team, it’s not just an opportunity for you to apply your knowledge to a role you love. It’s also a chance to build on your skills and expand them to new areas in your professional career.

Join the growing team at H.O. Penn Machinery today!



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