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Account Executive

Chesapeake Telephone Systems, Inc.
Millersville, MD Full Time
POSTED ON 12/2/2025 CLOSED ON 1/14/2026

What are the responsibilities and job description for the Account Executive position at Chesapeake Telephone Systems, Inc.?

About CTS

Founded in 1985, CTS (Chesapeake Telephone Systems) 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 alike, 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

Your Mission

Win New Business – Identify, engage, and close new SMB and enterprise customers

Grow Accounts – Deepen relationships with existing clients

Own the Number – Meet or exceed monthly/quarterly targets

Be the Trusted Advisor – Guide customers through the tech landscape

How You’ll Succeed

  • Prospect via phone, email, social and in-person networking, including networking events.
  • Deliver tailored presentations & demos
  • Negotiate contracts to signature
  • Uncover upsell/cross-sell opportunities across VoIP, UCaaS, cabling, surveillance & more
  • Maintain an accurate pipeline in our CRM
  • Forecast with discipline and hit your KPIs
  • Stay current on product updates and industry trends
  • Coordinate with engineering & support to ensure flawless delivery

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

· Preferred: Bachelor’s degree in Business, Marketing, or related field

Why CTS

· Established Brand: 40 years of reputation and an A BBB rating

· Innovative Portfolio: Sell best-of-breed UCaaS, networking, cloud, and security solutions

· Career Trajectory: Join a growing sales organization with clear advancement paths

· Local Roots, National Reach: Work from our Millersville HQ while closing deals nationwide

· Family Culture: Collaborative team that celebrates wins and invests in your success

Compensation includes a competitive base salary (based on experience) plus uncapped commissions, for an expected first-year on-target earnings of $65,000. There is potential for higher earnings based on available spiffs and bonuses during first of year employment.

Job Type: Full-time

Pay: $30,000.00 - $60,000.00 per year

Benefits:

  • 401(k)
  • Dental insurance
  • Health insurance
  • Life insurance
  • Paid time off

Work Location: In person

Salary : $30,000 - $60,000

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