Sales Development Representative Pilot Jobs (NOW HIRING)

Ignite Your Technology Sales Career.

Make Your Mark. Love Your Work.

Join the SpyGlass Sales Development Team

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

Our SpyGlass Business Foundation: Technology Sales

For more than 25 years, SpyGlass 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 SnapShot Audit, world-class ongoing technology expense management through SpyCare, and alignment of technology investments with strategic sourcing management. We also offer our exclusive energy management service, ePro+.

Sales Development Program:

Build a Technology Sales Career

At SpyGlass, 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 SpyGlass serving clients across healthcare, financial services, manufacturing, higher education, public sector, retail, and more. At SpyGlass, 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 SpyGlass, 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.

Sales Development Tiers

Tier 1: Sales Development Representative

Tier 2: Sales Development Representative II

Tier 3: Senior Sales Development Representative

Tier 4: Account Representative

Unlock Opportunity:

Day-to-Day, Skills, & Growth

Build core tech sales advisory capabilities, such as targeted outreach (calls, emails, and social touches), and booking meetings.

Gain valuable HubSpot 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.

What We're Looking For

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.

Required Skills and Experience:

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

Preferred Skills and Experience:

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

Direct sales/marketing

Benefits Offered:

Medical

Dental

Vision

STD

LTD

Voluntary Life

Accident

Identity Theft

Critical Illness

Hospital Indemnity

Join an Industry on the Rise

The technology advisory industry is experiencing significant growth. Organizations are focused on technology optimization, creating demand for skilled technology sales professionals who understand cost management, procurement strategy, and vendor relationships. The SpyGlass Sales Development Program is built on a nationally recognized technology sales playbook proven to develop high-performing technology sales professionals.

Nikki Guthrie
Vice President, Talent Management
[email protected] (c) 216.906.4141