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