Job Title

Senior Outside Sales Executive - Managed IT ServicesNorthern Virginia and Washington, DCTerritory:Northern VA, Washington, DC, and Southern MD (field-based)Reports To:VP of SalesCompensation:Strong base + uncapped commission------------------------------------------------------------------------This 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 potentialthis 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 manufacturing- Other 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 Youll Be Responsible ForOwning and Growing the Territory- Full ownership of new business development in Northern VA, Washington DC, and Southern MD.- Prospecting, networking, referrals, and strategic outreachyou are expected to hunt- Running introductory meetings, onsite discovery, and executive-level conversationsSelling 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-endfrom discovery to proposal to close- Closing recurring revenue agreements and building a long-term book of businessBecoming a Trusted Advisor- Building deep relationships with owners, partners, CFOs, COOs, and executive leadership- Establishing credibility as an MSP and security advisornot 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 Were Looking ForThis 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 mindsetyou create momentum, not wait for it- Experience selling into professional services or regulated SMBs is a strong plusThis 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 and 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 ESOPEqual Opportunity Employer M/F/Disabled/Veteran