Sales Development Representative

About the role

Join the SpyGlass Sales Development Team and place yourself at the forefront of technology sales—an industry experiencing widespread growth. As a Sales Development Representative (SDR), you’ll take the first step toward tech sales development, skill-building, and career progression in a business-focused environment. SpyGlass is a technology advisory leader with over 25 years of experience, providing solutions to more than 16,000 clients across the U.S. and Canada.

You’ll sell solutions that deliver measurable results, including $140 million in annual technology service savings for businesses in healthcare, financial services, manufacturing, higher education, public sector, retail, and more. The Sales Development Program combines intensive training, daily coaching, and a clearly defined promotion path from SDR to full-cycle Account Executive, with opportunities for relocation as you advance.

SpyGlass is recognized as a top workplace, earning honors such as Top Workplaces, Crain’s 52 Fastest Growing Companies, and the Northeast Ohio Smart Culture Award. This reputation ensures SDRs develop in a high-standard, high-support environment where success is noticed and rewarded.

Sales Development Tiers

• Tier 1: Sales Development Representative
• Tier 2: Sales Development Representative II
• Tier 3: Senior Sales Development Representative
• Tier 4: Account Representative

Responsibilities

• Build core tech sales advisory capabilities, including targeted outreach (calls, emails, and social touches) and booking meetings
• Gain education on HubSpot CRM and modern go-to-market tools, tracking activity and outcomes
• Progress through multiple levels of the sales organization to develop into a full-cycle sales advisor

Requirements

We’re seeking candidates eager to begin or build a technology sales career, or those with demonstrated success in B2B sales ready to grow with us.

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

Preferred Skills

• 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 multi-stakeholder opportunities
• Proficiency with CRM tools (HubSpot experience is a plus)
• A self-starter mindset with the drive to succeed in a performance-based environment

Benefits

• Medical
• Dental
• Vision
• Short-Term Disability (STD)
• Long-Term Disability (LTD)
• Voluntary Life Insurance
• Accident Insurance
• Identity Theft Protection
• Critical Illness Insurance
• Hospital Indemnity

Compensation

Competitive compensation with a newly enhanced structure that rewards hustle and results.