Outside Sales Account Executive

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

Outside Sales Account Executive – Managed IT Services

Northern Virginia & Washington, DC

Territory: Northern VA, Washington, DC, & Southern MD (field-based)

Reports To: VP of Sales

Compensation: $60k + uncapped commission + monthly profit sharing (OTE of $90-$100k)

Launch Your Career in Technology Sales

We're looking for an ambitious, driven sales professional who enjoys meeting new people, building relationships, and winning new business. You may not have years of MSP experience yet—and that's okay. If you've had success in B2B sales, are comfortable prospecting, and want to develop into a top-performing technology sales professional, we'll provide the coaching, support, and resources to help you succeed.

This is a field-based, new business role focused on helping small and midsize businesses improve their technology, cybersecurity, and business operations through long-term managed IT services.

About Us

We are a mature IT managed services provider with strong client retention. Our clients are typically 10-200 users (average ~40 users) across:

• Professional services (legal, CPA, architecture, engineering)
• Construction and manufacturing
• Other SMBs that value stability, security, and long-term partnerships

We sell long-term managed services agreements, not one-off projects, and we support our sales team with marketing materials, technical leadership, and proven delivery.

What We Offer

• Competitive base salary + uncapped commissions + monthly profit sharing
• Strong benefits package (including health, dental, and 401(k) matching)
• Employee ownership through the WingSwept ESOP
• Sales coaching, mentorship, and professional development
• Technical experts to support solution design and client presentations
• Marketing resources and proven sales tools
• A stable, established MSP with excellent client retention
• Clear opportunities for career advancement into senior sales roles

What You’ll Be Responsible For

Owning and Growing the Territory

• Develop relationships with prospective clients throughout Northern Virginia, Washington, DC, and Southern Maryland.
• Prospect through networking, referrals, community involvement, and strategic outreach.
• Follow up on qualified appointments generated by our Sales Development Representatives.
• Consistently build and manage your sales pipeline.

Selling MSP the Right Way

• Source recurring revenue agreements and building a long-term book of business
• Join the VP, Sales and CEO in consultative discovery focused on business risk, security, growth, and operations
• Sell managed services, cybersecurity, cloud, and strategic IT roadmaps
• Work with internal technical resources to scope and price solutions

Becoming a Trusted Advisor

• Build relationships with business owners, executives, and decision-makers.
• Represent the company professionally at networking events and local business organizations.
• Stay engaged with clients after the sale to identify expansion opportunities and generate referrals.

Who We’re Looking For

• 1-3 years of B2B outside sales experience (technology sales is a plus but not required)
• A history of meeting or exceeding sales goals
• Strong communication and relationship-building skills
• Confidence speaking with business owners and executives
• A competitive, self-motivated attitude and willingness to prospect
• A desire to build a long-term career in technology sales
• A true hunter mindset—you create momentum, not wait for it
• A competitive, self-motivated attitude and willingness to prospect
• A desire to build a long-term career in technology sales

You’ll Be Successful If You

• Enjoy meeting new people and building relationships
• Are naturally curious and ask thoughtful questions
• Take initiative and don't wait for opportunities to come to you
• Are coachable and eager to continuously improve
• Thrive when your success is directly tied to your effort and performance

Equal Opportunity Employer M/F/Disabled/Veteran