Director of Sales – Managed IT Services

Location - Westborough, MA

Employment Type - Full Time

Logistics - Hybrid/Remote

Position Overview

We are seeking an experienced Director of Sales to lead new business growth for a growing Managed Services Provider. This is a hands-on sales leadership role for someone who can build strategy, create accountability, develop a repeatable sales process, and still be comfortable getting directly involved in winning new business.

The Director of Sales will own the sales function, including pipeline development, forecasting, team performance, and revenue growth. This role is ideal for a proven hunter and sales leader who understands how to build a high-performing sales organization rather than simply manage an existing book of business.

Key Responsibilities

• Develop and execute the company's sales strategy to drive new client acquisition and recurring revenue growth.
• Own new-logo sales performance and achievement of company revenue goals.
• Build a consistent, measurable sales process from prospecting through close.
• Generate new opportunities through outbound prospecting, networking, referrals, strategic partnerships, events, and other business development channels.
• Lead by example and participate directly in prospecting, discovery, presentations, negotiations, and closing opportunities.
• Build, coach, develop, and hold the sales team accountable to clearly defined goals and expectations.
• Establish KPIs around activity, pipeline generation, conversion rates, recurring revenue, forecasting, and closed business.
• Maintain a healthy and predictable sales pipeline.
• Conduct regular pipeline reviews and provide accurate sales forecasts to executive leadership.
• Identify target markets, ideal client profiles, verticals, and opportunities for expansion.
• Develop messaging, sales tools, and processes that clearly communicate the company's value proposition.
• Partner with technical and operational leadership to scope opportunities and develop solutions that align with client needs.
• Sell managed IT, cybersecurity, cloud, and related technology solutions based on business outcomes and value.
• Develop relationships with business owners, executives, and other key decision-makers.
• Evaluate sales tools, technology, and processes and continuously identify opportunities for improvement.
• Help recruit, onboard, and develop additional sales talent as the company grows.
• Ensure a smooth transition from sales to onboarding and service delivery.

What We’re Looking For

• 7+ years of B2B sales experience with a track record of generating and closing new business.
• Previous sales leadership experience with responsibility for team performance and revenue growth.
• MSP, managed IT services, cybersecurity, cloud, telecom, or technology services experience strongly preferred.
• Proven success as a hunter, not solely an account manager or sales team administrator.
• Experience building or improving a repeatable sales process.
• Strong understanding of pipeline management, forecasting, sales KPIs, and CRM discipline.
• Experience coaching salespeople and creating accountability around performance.
• Ability to prospect and generate opportunities independently rather than relying solely on inbound leads.
• Strong executive-level discovery, presentation, negotiation, and closing skills.
• Ability to translate technical solutions into business value for non-technical decision-makers.
• Experience selling recurring revenue or long-term service agreements preferred.
• Strategic thinker who is also comfortable being hands-on and executing.
• Strong leadership, communication, and relationship-building skills.
• Data-driven approach to evaluating sales performance and making decisions.

What Success Looks Like

A successful Director of Sales creates a predictable engine for new business growth. You understand where opportunities are coming from, what is moving through the pipeline, where deals are getting stuck, and what the team needs to do differently to improve results.

You can set the strategy and execute it, coach and hold a team accountable while still being willing to get into a deal yourself, and build the processes and discipline necessary to consistently turn prospects into long-term managed services clients.

This is an opportunity for a sales leader who wants to have a meaningful impact on the growth, direction, and future of an MSP.