Outside Sales Account Executive

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)

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.

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.

• Competitive base salary + uncapped commissions + monthly profit sharing
• Strong benefits package (including health, dental, and 401(k) matching)
• Employee ownership through the Wing Swept 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

• 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.

• 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

• 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.

• 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

• 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