Senior Outside Sales Executive

Senior Outside Sales Executive - Managed IT ServicesNorthern Virginia & Washington, DCTerritory: Northern VA, Washington, DC, & Southern MD (field-based)Reports To: VP of SalesCompensation: Strong base + uncapped commissionThis Role Is for Proven SMB HuntersWe 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 UsWe 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 manufacturingOther SMBs that value stability, security, and long-term partnershipsWe 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 ForOwning and Growing the TerritoryFull ownership of new business development in Northern VA, Washington DC, and Southern MD.Prospecting, networking, referrals, and strategic outreach—you are expected to huntRunning introductory meetings, onsite discovery, and executive-level conversationsSelling MSP the Right WayLeading consultative discovery focused on business risk, security, growth, and operationsSelling managed services, cybersecurity, cloud, and strategic IT roadmapsWorking with internal technical resources to scope and price solutionsManaging deals end-to-end—from discovery to proposal to closeClosing recurring revenue agreements and building a long-term book of businessBecoming a Trusted AdvisorBuilding deep relationships with owners, partners, CFOs, COOs, and executive leadershipEstablishing credibility as an MSP and security advisor—not a commodity vendorDriving expansions, referrals, and long-term account growth post-closeRepresenting the company at networking groups, industry events, and local associationsWho We’re Looking ForThis Role Is a Fit If You Have:Minimum 5+ years of B2B sales experience, with direct MSP experience strongly preferredA proven track record closing managed services agreementsExperience selling recurring revenue to SMBs (10-200 users)Comfort running in-person meetings and executive-level conversationsA true hunter mindset—you create momentum, not wait for itExperience selling into professional services or regulated SMBs is a strong plusThis Role Is NOT a Fit If YouAre new to MSP or IT salesPrefer account management over huntingNeed heavy structure, scripts, or micromanagementAre uncomfortable owning your own pipeline and territoryWhat Success Looks LikeA consistent, self-generated pipeline of MSP opportunitiesClosed-won managed services clients with long-term contractsPredictable monthly and quarterly performanceStrong local reputation and referral network in Northern VA & DC, Southern MDGrowing recurring revenue year over yearWhat We OfferCompetitive base salary with uncapped commissionsStrong service delivery and leadership backing your salesAutonomy to run your day-to-day activities in your territoryA stable MSP with real scale, resources, and client retentionLong-term career opportunity for top performersEmployee ownership through the WingSwept ESOP Equal Opportunity Employer M/F/Disabled/Veteran