Director of Sales

Access One•Chicago, IL

26d•$150,000 - $170,000

About The Position

Access One, Inc. is seeking a 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 accountable for overall sales performance, new business acquisition, existing-customer growth, and recurring revenue expansion. The Director will establish a consistent, 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 role involving prospect meetings, client engagements, sales calls, and field appointments to coach team members, support strategic opportunities, and model effective sales execution. The Director will oversee sales strategy, team development, customer retention and expansion, Salesforce adoption, forecasting, performance management, and collaboration with executive and cross-functional leaders. Compensation includes a base salary of $150,000–$170,000 annually and target on-target earnings of $300,000–$340,000 annually. Target variable compensation is $150,000–$170,000, based on established performance objectives. The company offers a competitive benefits package. Performance is 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 sales leadership or management.
Prior sales experience in an MSP or IT services environment.
Demonstrated success leading sales teams to achieve 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 in 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 accountability for the Direct/Outside Sales and Account Management/Inside Sales teams.
Mentor, coach, recruit, train, and develop sales professionals; set performance expectations, goals, KPIs, and accountability measures.
Conduct one-on-one meetings, team meetings, performance reviews, and coaching sessions.
Participate in prospect meetings, discovery calls, customer presentations, sales calls, and field appointments to coach and support the teams.
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 business acquisition; coach consultative selling, solution positioning, negotiation, and closing.
Monitor quotas, pipeline coverage, conversion rates, productivity, and new recurring revenue objectives; develop strategies to improve sales productivity, sales cycles, and win rates.
Lead account management strategies for retaining and growing existing customer relationships through upselling, cross-selling, renewals, and additional service adoption.
Set measurable expectations for account expansion, customer retention, renewal activity, and sales productivity.
Coordinate with Operations, Service Delivery, and Customer Support to address customer concerns, identify growth opportunities, and improve customer satisfaction.
Ensure effective coordination between Direct Sales and Account Management, including customer transitions, account ownership, and ongoing revenue development.
Own Salesforce adoption, data integrity, and CRM accountability across both sales organizations.
Maintain accurate opportunity, account activity, pipeline, forecasting, and reporting practices; develop dashboards and KPIs.
Conduct regular pipeline reviews and forecasting meetings, analyze sales data, and provide timely forecasts and performance updates to executive leadership.
Implement and optimize sales processes, workflows, reporting standards, and performance management practices.
Develop and execute sales strategies aligned with company revenue and growth objectives.
Collaborate with Executive Leadership, Technical Operations, Service Delivery, Finance, and Marketing on sales initiatives, pricing, solution packaging, competitive positioning, and go-to-market execution.
Support sales compensation plans and incentive programs, and evaluate sales processes, organizational structure, and resource allocation.
Serve on the company leadership team and advise on sales performance, market opportunities, and revenue growth.