Sales Executive

Sales Executive

Winsor Consulting Group is a leading Managed Service Provider (MSP) committed to delivering exceptional IT and infrastructure solutions to our clients. With expertise spanning Managed Services, Professional Services, Security & Compliance, Data Center and Colocation, and Infrastructure-as-a-Service (IaaS), Winsor helps organizations modernize, secure, and scale their technology environments.

We are seeking an experienced and results-driven Sales Executive to expand our market presence and generate new business across Winsor's technology portfolio, with a particular focus on Data Center, Colocation, IaaS, Managed Services, and Professional Services.

The Sales Executive will play a critical role in driving new business development and revenue growth for Winsor Consulting Group. This position is responsible for identifying, qualifying, and closing new client opportunities, with a strong emphasis on Data Center and Colocation solutions, while also supporting Managed Services and Professional Services sales.

The ideal candidate is a proactive hunter with strong relationship-building skills, capable of navigating complex sales cycles and aligning technical solutions with business outcomes. This individual will work closely with Sales Engineering, Marketing, and Service Operations to deliver tailored solutions that meet client needs.

Job Duties:

• Identify, prospect, and develop new business opportunities within target markets.
• Drive revenue growth through the sale of Data Center, Colocation, Managed Services, and Professional Services offerings.
• Conduct client discovery meetings to understand business, technical, and operational requirements.
• Develop and present tailored solutions in collaboration with Sales Engineering and technical teams.
• Build and maintain a strong sales pipeline, accurately forecasting opportunities and revenue.
• Manage the full sales cycle from initial outreach through contract execution.
• Establish and maintain long-term client relationships, acting as a trusted advisor.
• Collaborate with internal teams (Sales Engineering, Marketing, Service Operations, and Leadership) to align solutions and ensure successful delivery.
• Participate in proposal development, pricing strategy, and contract negotiations.
• Maintain accurate and up-to-date records in CRM systems (e.g., HubSpot, ConnectWise Manage).
• Represent Winsor at networking events, industry events, and client meetings.
• Stay informed on industry trends, competitive offerings, and emerging technologies, particularly in Data Center and infrastructure services.
• Ensure smooth handoff of closed deals to implementation and service delivery teams.
• Meet or exceed assigned sales targets, KPIs, and activity metrics.

Preferred Skills:

• Strong understanding of Data Center, Colocation, and infrastructure solutions.
• Experience selling Managed Services and Professional Services engagements.
• Proven ability to generate new business and close complex deals.
• Excellent communication, presentation, and interpersonal skills.
• Ability to translate technical solutions into business value.
• Strong organizational and pipeline management skills.
• Proficiency in CRM systems (e.g., HubSpot, ConnectWise Manage).
• Self-motivated with a results-driven mindset.
• Ability to work independently while collaborating effectively across teams.
• Strong negotiation and problem-solving skills.

Experience:

• 3+ years of experience in B2B sales, preferably in IT services, Data Center, or technology solutions.
• Proven track record of meeting or exceeding sales quotas.
• Experience with MSP, infrastructure, or cloud-related sales is strongly preferred

Preferred Certifications:

• Relevant sales training or certifications (e.g., Sandler, MEDDICC, or equivalent)
• Vendor or technology certifications related to Data Center, cloud, or infrastructure (preferred but not required)

Education:

• High school diploma or equivalent required; Bachelor's degree in Business, Marketing, or a related field is preferred.

Commission Structure:

Compensation is comprised of base salary plus performance-based commission. Winsor's commission structure rewards new revenue, profitable solutions, and long-term client relationships, with commission calculations varying by solution type.

Managed Services and ColocationEarn up to 100% of the first month's gross margin on qualifying 36-month agreements, paid over seven months. Commission rates are adjusted based on the term of the agreement.

Staff AugmentationEarn 4% of qualifying labor fees on Staff Augmentation engagements, paid based on applicable client payments and service delivery.

Professional Services ProjectsEarn 6.5% of qualifying Professional Services labor revenue, paid as client payments are received.

Hardware and One-Time SoftwareEarn 10% of gross margin on qualifying hardware and one-time software sales.

SaaS AgreementsEarn up to 100% of the first month's gross margin, based on the term of the agreement.

Referrals and Carrier OpportunitiesEarn 10% of qualifying net commissions received by Winsor from referral and carrier opportunities.

Partner Resale OpportunitiesEarn 10% of gross margin on qualifying partner resale opportunities.

Commissions are subject to the terms and eligibility requirements of Winsor Consulting Group's applicable Sales Commission Agreement and are generally earned and paid following client payment.