WingSwept · 6 days ago
Senior Outside Sales Executive
Chantilly, VA
Full-time
Hybrid
Senior Level
5+ years expWingSwept is a mature IT managed services provider with strong client retention. They are seeking a Senior Outside Sales Executive to own and grow their territory by developing new business, selling managed services, and building trusted relationships with SMB clients.
B2BInformation ServicesInformation TechnologyProfessional ServicesSoftware
Responsibilities
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
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
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
Qualification
Required
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
Benefits
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
Company
WingSwept
WingSwept is a B2B technology services company that provides Managed IT Services and tech support to small and mid-size businesses.
11-50 employees
Funding
Current Stage
Early StageLeadership Team
Jay Strickland
Founder & CEO
April Strickland
VP, Human Resources
Recent News
PRNewswire Asia
2022-01-15
Company data provided by crunchbase