Outside Sales Account Executive - Managed IT Services

WingSwept; Chantilly (VA); On-site; USD 60,000 - 100,000; Full time

Benefits offered by this job

Health benefits

401(k) matching

Employee ownership (ESOP)

Sales coaching and tools

Marketing support

Job summary

WingSwept is seeking an Outside Sales Account Executive to drive new business in Northern Virginia, Washington, DC, and Southern Maryland. This field-based role focuses on long-term managed IT services, cybersecurity, and cloud roadmaps for SMBs.

You’ll be coached by leadership, supported by marketing resources, and rewarded with a base salary plus uncapped commissions and a monthly profit share (OTE $90-$100k). ESOP ownership and career advancement are offered.

Qualifications

• 1–3 years of B2B outside sales experience.
• History of meeting or exceeding sales goals.
• Strong communication and relationship-building skills.
• Confidence speaking with business owners and executives.
• Competitive, self-motivated with a hunter mindset.

Responsibilities

• Develop relationships with prospective clients in Northern Virginia, Washington, DC, and Southern Maryland.
• Prospect through networking, referrals, community involvement, and strategic outreach.
• Follow up on qualified appointments and manage your sales pipeline.
• Sell managed services, cybersecurity, cloud, and IT roadmaps.
• Collaborate with internal resources to scope and price solutions.

Skills

B2B outside sales

Prospecting

Relationship building

Communication

Hunter mindset

Technology sales

Job description

WingSwept is seeking an Outside Sales Account Executive to drive new business in Northern Virginia, Washington, DC, and Southern Maryland. This field-based role focuses on long-term managed IT services, cybersecurity, and cloud roadmaps for SMBs.

You’ll be coached by leadership, supported by marketing resources, and rewarded with a base salary plus uncapped commissions and a monthly profit share (OTE $90-$100k). ESOP ownership and career advancement are offered.