Senior Outside Sales Executive

About the role

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.

Responsibilities

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.

Requirements

• 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.

Qualifications

• 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

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

Pay

Compensation: Strong base + uncapped commission

Schedule

Field-based