Director of Sales

Access One•Chicago, IL
•$300,000 - $340,000

About The Position

Access One, Inc. is seeking an experienced, hands-on Director of Sales to lead its Direct/Outside Sales and Account Management/Inside Sales organizations in a Managed Service Provider (MSP) and telecom environment. The role is responsible for sales performance, new business acquisition, growth of existing customers, and recurring revenue expansion. The Director will establish a results-driven sales culture and align both teams around revenue goals, customer experience, pipeline development, and long-term account growth. This is an active leadership position involving prospect meetings, client engagements, sales calls, and field appointments to coach employees, support strategic opportunities, and demonstrate effective sales execution. The Director will own Salesforce adoption and accountability, forecasting, performance measurement, and cross-functional sales strategy. Success will be measured by new business acquisition, recurring revenue growth, existing-customer expansion, customer retention, and achievement of revenue objectives.

Requirements

  • At least 7 years of experience in B2B technology, IT services, or solution-based sales, including at least 3 years in a sales leadership or management role.
  • Prior experience selling in an MSP or IT services environment.
  • Demonstrated success leading sales teams to meet or exceed revenue goals in a recurring-revenue or services-based business model.
  • Experience managing new-business sales teams and understanding account management, customer retention, and existing-customer revenue expansion.
  • Ability to develop sales strategies, manage performance, and drive accountability across multiple sales functions.
  • Hands-on leadership style and willingness to 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, including the ability to turn sales metrics into actionable business strategies.
  • Ability to collaborate effectively across technical, operational, and executive teams.

Nice To Haves

  • Telecom industry experience, particularly with connectivity, UCaaS/VoIP, SD-WAN, or carrier services.
  • 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.

Responsibilities

  • Lead and provide direction and accountability for the Direct/Outside Sales and Account Management/Inside Sales teams.
  • Mentor, coach, and develop sales professionals to achieve revenue targets; establish goals, KPIs, expectations, and accountability measures.
  • Conduct one-on-one meetings, team meetings, performance reviews, and coaching sessions; recruit, train, and develop sales professionals.
  • Participate in prospect meetings, discovery calls, customer presentations, sales calls, and field appointments to coach teams and support opportunities.
  • Oversee new-customer acquisition and recurring revenue generation for Managed IT, Cybersecurity, UCaaS, Internet, and related technology services.
  • Drive prospecting, pipeline development, opportunity management, and new-customer acquisition; coach consultative selling, discovery, solution positioning, differentiation, and closing.
  • Monitor quotas, pipeline coverage, conversion rates, and recurring revenue objectives; implement strategies to improve productivity, shorten sales cycles, and increase win rates.
  • Lead account management and inside sales activities focused on customer relationships, retention, renewals, upselling, cross-selling, and service adoption.
  • Develop account growth strategies and performance expectations for expansion, retention, renewals, and sales productivity.
  • Coordinate with Operations, Service Delivery, and Customer Support to address customer concerns, identify growth opportunities, and improve customer satisfaction.
  • Coordinate Direct Sales and Account Management, including customer transitions, account ownership, and continued revenue development.
  • Own Salesforce adoption, data integrity, and CRM accountability; ensure accurate opportunity, account activity, pipeline, forecast, and reporting management.
  • Develop and maintain sales dashboards and KPIs; conduct pipeline reviews and forecasting meetings; analyze sales data and report timely forecasts and performance updates to executive leadership.
  • Implement and optimize sales processes, workflows, and reporting standards.
  • Develop sales strategies aligned with company revenue and growth objectives and collaborate with executive, technical, operational, finance, and marketing teams.
  • Partner with internal teams on solution packaging, pricing, competitive positioning, and go-to-market execution.
  • Support sales compensation plans, incentive programs, and performance management strategies; evaluate sales processes, organizational structure, and resource allocation.
  • Serve on the company's leadership team, providing insight and recommendations on sales performance, market opportunities, and revenue growth.

Benefits

  • Competitive company benefits package.
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