Be an Early Applicant
The Role
Prospect and close new SMB and enterprise customers for voice, data, and video solutions. Present demos, negotiate contracts, manage pipeline in CRM, identify upsell/cross-sell opportunities, coordinate delivery with engineering and support, and meet monthly/quarterly sales targets.
Summary Generated by Built In
About Chesapeake Telephone Systems (CTS)Founded in 1985, Chesapeake Telephone Systems (CTS) is a trusted, family-owned provider of cutting-edge Voice, Data, and Video solutions for 5,000+ customers across Maryland, Washington DC, Northern Virginia, and the Mid-Atlantic. We serve neighborhood shops and nationwide enterprise networks a like hold an A+ BBB rating, and were honored as the U.S. SBA “Maryland Family-Owned Small Business of the Year.” What You’ll Do
Key Responsibilities
Prospect via phone, email, social and in-person networking,
including networking events.
Deliver tailored presentations & demos
Negotiate contracts to signature Win New Business Identify, engage, and close new SMB and enterprise customers. Your Mission How You’ll Succeed
Uncover upsell/cross-sell opportunities across VoIP, UCaaS,
cabling, surveillance & more Grow Accounts Deepen relationships with existing clients+ + Maintain an accurate pipeline in our CRM Forecast with discipline and hit your KPIs Own the Number Meet or exceed monthly/quarterly targets+ + Stay current on product updates and industry trends Coordinate with engineering & support to ensure flawless delivery Be the Trusted Advisor Guide customers through the tech landscape
Skills, Knowledge and Expertise
What You Bring+ + + 2+ years success in B2B Sales, Business Development, or Account Management Proven hunter mentality with strong negotiation and closing skills Excellent written & verbal communication—storyteller and active listener Comfortable managing deals in a modern CRM (Pipedrive)+ + + + Track record of building long-term client relationships. Team-oriented, self-directed, and highly accountable Nice-to-have: background in technology or telecommunications Bachelor’s degree in Business, Marketing, or related field
About
AAWDC is a nonprofit corporation that provides innovative, high-quality workforce development services to Anne Arundel County businesses and residents. We are the bridge between understanding the workforce and talent development needs of local and regional businesses and preparing individuals to meet their full career potential.
Skills Required
- 2+ years success in B2B Sales, Business Development, or Account Management
- Proven hunter mentality with strong negotiation and closing skills
- Excellent written and verbal communication; storytelling and active listening
- Comfortable managing deals in a modern CRM (Pipedrive)
- Track record of building long-term client relationships
- Team-oriented, self-directed, and highly accountable
- Background in technology or telecommunications
- Bachelor's degree in Business, Marketing, or related field
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The Company
What We Do
AAWDC is a nonprofit corporation that provides innovative, high-quality workforce development services to Anne Arundel County businesses and residents, helping them build, attract, retain, and upskill talent.

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