Sales Development Representative

Join the Spy Glass Sales Development Team.

The SALES DEVELOPMENT role at Spy Glass places you at the forefront of TECHNOLOGY SALES — an industry experiencing widespread growth. By joining our technology advisory organization, your role at Spy Glass is the first step toward tech sales development, skill-building, and progression in a business-focused career.

For more than 25 years, Spy Glass has been a technology advisory industry leader, providing solutions to over 16,000 clients throughout the U.S. and Canada. In virtually every type of business, through every sector, we help clients make smarter tech savings decisions with our proven Snap Shot Audit®, world‑class ongoing technology expense management through Spy Care®, and alignment of technology investments with strategic sourcing management
. We also offer our exclusive energy management service,
ePro+®.

At Spy Glass, our Sales Development Program is built on a nationally recognized technology sales playbook proven to develop high‑performing technology sales professionals. You won’t just be learning to sell; you’ll be selling a solution that has delivered real, measurable results for 25+ years to organizations across the U.S. and Canada, including $140 million in annual technology service savings uncovered for businesses in virtually every industry.

We combine intensive training, daily coaching, and a clearly defined promotion path for advancement from SDR to full‑cycle Account Executive. The market you’ll be selling into is vast and growing, with Spy Glass serving clients across healthcare, financial services, manufacturing, higher education, public sector, retail, and more. At Spy Glass, the opportunities you pursue as you grow into a full Account Executive are broad, varied, and built to last.

We are widely known in the technology expense management space as a go‑to starting point for B2B tech sales talent, with a culture that has earned Top Workplaces recognition multiple years in a row — alongside honors including the Crain’s 52 Fastest Growing Companies, the Weatherhead 100, and the Northeast Ohio Smart Culture Award. That reputation means SDRs are developed in a high‑standard, high‑support environment where success is noticed and rewarded.

When you join Spy Glass, you’re starting and thriving in a place with the stability, growth trajectory, and industry standing to develop a long‑term career in technology sales.

• Build core tech sales advisory capabilities, such as targeted outreach (calls, emails, and social touches), and booking meetings.
• Gain valuable Hub Spot CRM and modern go‑to‑market tool education alongside the ability to track activity and outcomes.
• Progress through multiple levels of our sales organization to quickly develop into a full‑cycle sales advisor — with major market relocation opportunities available.
• Competitive compensation. Our newly enhanced structure rewards your hustle and results.

We're seeking Sales Development Representative candidates who are eager to begin and build a technology sales career, and/or bring demonstrated success in B2B sales and are ready to grow with us.

• 0 – 2+ years of experience in Sales, Business Development, or a related field

• Excellent communication and presentation skills — ability to engage C‑suite and VP‑level decision makers
• Competitive, coachable, and confident to engage with decision‑makers in real time
• Strong consultative selling skills — ability to diagnose client needs and present ROI‑driven solutions
• Experience managing full‑cycle sales processes and…