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Reports to: Sales Manager

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, and Data Center solutions, Winsor helps organizations modernize, secure, and scale their technology environments. We are seeking a driven and results-oriented Sales Executive to expand our market presence, with a focus on Data Center and Colocation 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.

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.

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.

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

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)

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

Compensation is comprised of base salary plus commission. Commission is performance-based and tied directly to gross margin on closed deals. See the list below for a breakdown of commission opportunities.

Earn up to 100% of the first month’s gross margin on 36-month agreements, paid over 7 months (shorter terms prorated).

Earn 6.5% of total labor revenue, paid as client invoices are received.

Earn 10% of gross margin.

Earn up to 100% of the first month’s gross margin (term-dependent).

Earn 10–15% of net commissions or margin received.

Commissions are paid after client payment is received and are structured to reward long-term, high-margin agreements.