Senior Outside Sales Executive

Senior Outside Sales Executive – Managed IT Services

Northern Virginia & Washington, DC

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

Reports To: VP of Sales

Compensation: Strong base uncapped commission

This Role Is for Proven SMB Hunters

We are not looking for a junior seller, order taker, or someone learning MSP sales for the first time.

We are hiring a senior, field-based sales professional who has already sold services to local SMBs, understands recurring revenue, and knows how to build trust with executive decision-makers.

If you have closed service agreements before, know how to run a discovery-driven sales process, and want the autonomy to own a territory with real earning potential—this role is built for you.

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 You’ll Be Responsible For

Owning and Growing the Territory

• Full ownership of new business development in Northern VA, Washington DC, and Southern MD.
• Prospecting, networking, referrals, and strategic outreach—you are expected to hunt
• Running introductory meetings, onsite discovery, and executive-level conversations
  
  
  

Selling MSP the Right Way

• Leading consultative discovery focused on business risk, security, growth, and operations
• Selling managed services, cybersecurity, cloud, and strategic IT roadmaps
• Working with internal technical resources to scope and price solutions
• Managing deals end-to-end—from discovery to proposal to close
• Closing recurring revenue agreements and building a long-term book of business
  
  
  

Becoming a Trusted Advisor

• Building deep relationships with owners, partners, CFOs, COOs, and executive leadership
• Establishing credibility as an MSP and security advisor—not a commodity vendor
• Driving expansions, referrals, and long-term account growth post-close
• Representing the company at networking groups, industry events, and local associations
  
  
  

Who We’re Looking For

This Role Is a Fit If You Have:

• Minimum 5 years of B2B sales experience, with direct MSP experience strongly preferred
• A proven track record closing managed services agreements
• Experience selling recurring revenue to SMBs (10–200 users)
• Comfort running in-person meetings and executive-level conversations
• A true hunter mindset—you create momentum, not wait for it
• Experience selling into professional services or regulated SMBs is a strong plus
  
  
  

This Role Is NOT a Fit If You:

• Are new to MSP or IT sales
• Prefer account management over hunting
• Need heavy structure, scripts, or micromanagement
• Are uncomfortable owning your own pipeline and territory
  
  
  

What Success Looks Like

• A consistent, self-generated pipeline of MSP opportunities
• Closed-won managed services clients with long-term contracts
• Predictable monthly and quarterly performance
• Strong local reputation and referral network in Northern VA & DC, Southern MD
• Growing recurring revenue year over year
  
  
  

What We Offer

• Competitive base salary with uncapped commissions
• Strong service delivery and leadership backing your sales
• Autonomy to run your day-to-day activities in your territory
• A stable MSP with real scale, resources, and client retention
• Long-term career opportunity for top performers
• Employee ownership through the WingSwept ESOP
  
  
  

Equal Opportunity Employer M/F/Disabled/Veteran