Director of Sales

Access One; Chicago (IL); On-site; USD 150,000 - 170,000; Full time

Benefits offered by this job

Competitive benefits

Job summary

Access One is seeking an experienced Director of Sales to lead Direct/Outside Sales and Account Management/Inside Sales within a fast-paced MSP and Telecom environment in Chicago.

The role drives new business, existing customer growth, and recurring revenue, while coaching teams, shaping sales processes, and ensuring CRM discipline with Salesforce and accurate forecasting.

Qualifications

• 7+ years in B2B technology or IT services sales.
• Minimum 3 years in a sales leadership/management role.
• Experience in MSP or IT services environment required.
• Proven track record leading teams to revenue goals.
• Hands-on leadership style with field involvement.
• Strong Salesforce knowledge and CRM discipline.

Responsibilities

• Lead Direct/Outside Sales and Account Management/Inside Sales teams.
• Coach and develop sales professionals to exceed revenue targets.
• Set and track performance expectations, KPIs, and reviews.
• Participate in prospect meetings, client engagements, and field appointments.
• Collaborate with Operations, Service Delivery, and Customer Support.
• Coordinate between Direct Sales and Account Management for revenue growth.
• Drive forecasting accuracy and data-driven performance management.

Skills

Sales leadership

MSP/IT services knowledge

Salesforce

Forecasting

People development

Tools

Salesforce

Job description

We are seeking an experienced, hands‑on Director of Sales to lead both our Direct/Outside Sales and Account Management/Inside Sales organizations within a fast-paced Managed Service Provider (MSP) and Telecom environment.

This is a highly visible leadership role responsible for driving overall sales performance, new business acquisition, existing customer growth, and recurring revenue expansion across both teams. The Director of Sales will establish a consistent, results-driven sales culture while ensuring both teams are aligned on revenue goals, customer experience, pipeline development, and long-term account growth.

This is not a desk-only leadership position. The Director will actively participate in prospect meetings, client engagements, sales calls, and field appointments to coach team members, support strategic opportunities, and model high-impact sales execution. The ideal candidate has a strong understanding of the MSP sales cycle, experience leading both new business and account management functions, and a proven ability to develop high-performing sales teams. This individual must also be highly proficient in Salesforce, with commitment to CRM discipline, forecasting accuracy, and data-driven performance management.

Key Responsibilities

• Provide overall leadership, direction, and accountability for both the Direct/Outside Sales and Account Management/Inside Sales teams.
• Lead, mentor, coach, and develop sales professionals across both organizations to consistently achieve and exceed revenue targets.
• Establish clear performance expectations, sales goals, KPIs, and accountability measures for each team.
• Conduct regular one-on-one meetings, team meetings, performance reviews, and coaching sessions to drive individual and organizational improvement.
• Actively participate in prospect meetings, discovery calls, customer presentations, and field appointments to provide hands-on coaching and support.
• Recruit, train, and develop new sales professionals while identifying opportunities for advancement and professional growth.
• Foster a collaborative, high-performance sales culture focused on accountability, transparency, customer satisfaction, and continuous improvement.

Direct Sales & New Business Development:

• Oversee the Direct/Outside Sales team responsible for acquiring new customers and generating new recurring revenue through Managed IT, Cybersecurity, UCaaS, Internet, and related technology services.
• Drive consistent prospecting, pipeline development, opportunity management, and new customer acquisition.
• Coach sales representatives on consultative selling, discovery, solution positioning, competitive differentiation, and closing strategies.
• Participate in strategic sales opportunities and assist representatives in navigating complex sales cycles and negotiations.
• Monitor individual and team performance against sales quotas, pipeline coverage, conversion rates, and new recurring revenue objectives.
• Develop and implement strategies to improve sales productivity, shorten sales cycles, and increase overall win rates.
• Provide leadership and oversight to the Account Management/Inside Sales team responsible for managing, retaining, and growing existing customer relationships.
• Establish strategies to maximize revenue opportunities within the existing customer base through upselling, cross-selling, contract renewals, and additional service adoption.
• Ensure account managers maintain proactive customer engagement, strong relationships, and a consistent focus on identifying new business opportunities.
• Develop account growth strategies that increase customer value, recurring revenue, and long-term retention.
• Establish measurable performance expectations around account expansion, customer retention, renewal activity, and sales productivity.
• Work closely with Operations, Service Delivery, and Customer Support leadership to address customer concerns, identify growth opportunities, and strengthen overall customer satisfaction.
• Ensure effective coordination between Direct Sales and Account Management teams, including smooth customer transitions, clear account ownership, and ongoing revenue development.

Salesforce, Forecasting & Performance Management:

• Own Salesforce adoption, data integrity, and CRM accountability across both sales organizations.
• Ensure consistent and accurate management of sales opportunities, account activity, pipelines, forecasting, and reporting.
• Develop and maintain sales dashboards and KPIs that provide visibility into new business production, account growth, customer retention, and overall revenue performance.
• Conduct regular pipeline reviews and sales forecasting meetings with both teams.
• Analyze sales data to identify performance gaps, revenue opportunities, and areas for operational improvement.
• Provide accurate, timely, and actionable sales forecasts and performance updates for executive leadership.
• Implement and optimize sales processes, workflows, and reporting standards to improve efficiency and scalability.

Strategic Leadership & Cross-Functional Collaboration:

• Develop and execute sales strategies that align both sales organizations with the company's overall revenue and growth objectives.
• Collaborate with Executive Leadership, Technical Operations, Service Delivery, Finance, and Marketing teams to align sales initiatives with business priorities.
• Partner with internal teams to improve solution packaging, pricing strategies, competitive positioning, and go‑to‑market execution.
• Identify opportunities to improve coordination between new customer acquisition and existing account development.
• Support the development of sales compensation plans, incentive programs, and performance management strategies.
• Evaluate sales processes, organizational structure, and resource allocation to maximize team effectiveness.
• Serve as a key member of the company's leadership team, providing insight and recommendations regarding sales performance, market opportunities, and revenue growth.

Required Qualifications

• 7+ years of experience in B2B technology, IT services, or solution-based sales, including a minimum of 3 years in a sales leadership or management role.
• Prior experience selling within an MSP or IT services environment is required.
• Demonstrated success leading sales teams to achieve and exceed revenue goals in a recurring revenue or services-based business model.
• Experience managing new business sales teams, with a strong understanding of account management, customer retention, and existing customer revenue expansion.
• Proven ability to develop sales strategies, manage performance, and drive accountability across multiple sales functions.
• Hands‑on leadership style with a willingness to actively participate in sales calls, customer meetings, field appointments, and strategic opportunities.
• Strong working knowledge of Salesforce, including pipeline management, forecasting, dashboards, reporting, and CRM best practices.
• Strong analytical and financial acumen with the ability to translate sales metrics into actionable business strategies.
• Demonstrated ability to collaborate effectively across technical, operational, and executive teams.

Preferred Qualifications

• Telecom industry experience, particularly with connectivity, UCaaS/VoIP, SD-WAN, or carrier services.
• Previous experience overseeing both direct sales and account management or inside sales organizations.
• Experience scaling sales teams in a high‑growth MSP or technology services company.
• Salesforce administrator or advanced user certifications.
• Familiarity with MSP tools and ecosystems, including PSA, RMM, and cybersecurity platforms.
• Experience implementing or optimizing sales processes, CRM workflows, compensation structures, and sales performance reporting.
• Demonstrated success driving customer expansion, cross‑selling initiatives, and recurring revenue growth within an established customer base.

Salary & Benefits

• Base Salary Range: $150,000–$170,000 annually, depending on experience and qualifications.
• On-Target Earnings (OTE): $300,000–$340,000 annually.
• Target Variable Compensation: $150,000–$170,000 annually, based on achievement of established performance objectives.
• Compensation Structure: Target OTE is equivalent to 2x annual base salary, with incentive compensation tied to the performance of both the Direct Sales and Account Management/Inside Sales organizations.
• Benefits: Competitive company benefits package.

Salary & Benefits

• Base Salary Range: $150,000–$170,000 annually, depending on experience and qualifications.
• On-Target Earnings (OTE): $300,000–$340,000 annually.
• Target Variable Compensation: $150,000–$170,000 annually, based on achievement of established performance objectives.
• Compensation Structure: Target OTE is equivalent to 2x annual base salary, with incentive compensation tied to the performance of both the Direct Sales and Account Management/Inside Sales organizations.
• Benefits: Competitive company benefits package.

The Director of Sales will be measured on overall sales organization performance, including new business acquisition, recurring revenue growth, existing customer expansion, customer retention, and achievement of established revenue objectives.