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Join Our Team

At SpyGlass, we deliver smarter technology savings solutions powered by over two decades of experience throughout virtually every type of business, in every sector. As trusted technology advisors to 16,000+ clients, SpyGlass magnifies today’s technology cost challenges to provide a clear view for the future.


And just as we’re focused on providing industry-leading technology expense management solutions, we’re dedicated to the growth and well-being of our team.


Based in Westlake, Ohio, the SpyGlass team spans the U.S. and Canada with a collaborative spirit taking us into the future. We work hard, but we make sure to have fun and support one another along the way.

We’re Growing and Hiring!


SpyGlass is actively recruiting and hiring competitive candidates to join our Business-to-Business sales team! Entry Level Sales Representatives play an integral role in a rapidly growing company, have the chance to advance within the organization, and leverage sales training methods to establish a career within a highly specialized industry.

Begin and Grow with Us


For over 20 years, our team has been the key to our growth. Their efforts led to us being recognized as one of the region’s 100 Top Workplaces by the Cleveland Plain Dealer and one of the country’s fastest growing companies on the Crain’s 52Weatherhead 100 and Inc. 5000 lists — and we’re still growing.


At SpyGlass, we’re here to not only help you begin a career, but grow along with us.


For over 20 years, we have understood the complexities of managing technology service costs. Our initial technology expense management (TEM) SnapShot Audit has uncovered $140 million+ in annual technology service savings for clients throughout the U.S. and Canada.


Our team of hundreds of dedicated technology expense experts is led by our founders, Ed DeAngelo and Brad Clark. With a culture built on helping our customers save on technology, we strive to support success throughout their procurement journey.


As a client-oriented company, our collaborative process streamlines the steps to reach initial optimization. From there, we advise on the best sourcing and ongoing management solutions for our clients' needs.


With our industry-leading SnapShot Audits supported by a team of dedicated technology expense experts, we find savings in 99% of engagements. We comb through bills, contracts, usage reports and customer service records to find errors, overcharges, and inefficiencies for the ultimate technology expense savings. 

What does the sales position entail?

As an Entry Level Sales Representative, your role is fundamental to our sales process. Your role is to engage fiscal executives, gain an understanding of their business structure and function, and introduce our consultative process. As a Sales Development Representative, you are providing businesses the opportunity to learn how our analysis could further benefit their bottom line by generating interest and setting meetings with decision-makers!

Team-oriented? We need you!

If you are competitive, self-motivated, team-oriented, driven, and looking to grow with a company that promotes from within and provides extensive training…you’re looking in the right place.

What You Can Expect

Make an Impact on Day 1


A SpyGlass technology expense management career starts with a comprehensive training and ramp-up process that prepares you for your role ahead. We train you on the skills needed to get to the next step in your career — quickly.

Unmatched Company Culture


During work hours, our team is dedicated to reaching company goals in an energetic, modern and fun office environment. Outside of work, we not only spend time bonding through company activities, like dodgeball or volunteering, but we’re actually friends. It’s not uncommon for us to spend our free time together — a testament to the fact our company culture breeds great careers and great relationships with each other.

On top of that, we have a formal Well Being and Employee Engagement department tasked with making our company culture second to none by providing programming to improve our employees’ lives beyond receiving a paycheck.

Competitive Benefits Package


All of our employees have market-competitive compensation packages including salaries, and in some cases commissions and bonuses. In addition, we provide excellent medical, dental and life insurance, 401(k) with company contributions, paid vacations, Employee Assistance Plan and much more.

You might be asking…

Why get a job in Cleveland?

The better question is, why wouldn’t you come to SpyGlass to pursue your career goals? Cleveland is the 45th largest city in the United States and the second largest in Ohio after the state capital, Columbus, with a booming downtown business and housing market. And, don’t believe the stale stereotypes you hear about Cleveland. If you like sports, we have three major league sports teams. If you like the water, Lake Erie is our playground. If you like culture, we have amazing museums, theaters and park systems. If you want access to top notch doctors, we have access to world-class healthcare from Cleveland Clinic and University Hospitals.

Why should I work for SpyGlass over a larger company?

Because we’re growing rapidly and you can advance your career and compensation more quickly at SpyGlass than you can at a huge company. In addition to being the best-known company in the technology expense audit industry, we’re still growing. Our business model has always been to hire smart people who want to do big things in life at an early age. If you want to be professionally aggressive and be recognized for being smart and hard-working, SpyGlass is the place for you. If you want to be a number, take that other job at the Fortune whatever.

I want to relocate. Can SpyGlass make exploring the country a reality?

SpyGlass is growing rapidly and we need smart, trailblazing employees who are willing to push our service offerings into new markets all over the United States and Canada. Getting into new markets is our growth model and we’ve got the training programs and promotion opportunities to fulfill your dreams.

I want to stay in Cleveland. Why is SpyGlass an option?

Duh?! Because we’re headquartered here. Even though relocation is an option if you want to explore the country, that’ll never change the fact that our home is in Cleveland. At headquarters, we have sales, management, analytical, project management and administrative jobs all of which are great opportunities for those who bleed Cleveland Browns orange and would never want to leave.

Career Openings