Director of Sales

About Access One Access One is a business technology services and communications provider, dedicated to world-class technologies and an award-winning client experience. Founded in 1993, Access One strives to provide companies with seamless technology services that scale and evolve along with their business. Our goal is to be a trusted advisor to our clients, offering the world-class technology solutions that drive successful businesses. Our solutions are delivered by a team of knowledgeable professionals who are committed to providing an unrivaled level of client service. Our custom-tailored solutions can be delivered modularly, or as a complete, end-to-end service. The components of service can be combined into an end-to-end managed technology solution, or purchased independently for seamless integration with your existing technology suite. Whichever option is selected, Access One provides its services in a consultative, hands-on, client-focused manner. We offer an unrivaled level of accountability for our clients’ communications, managed IT and cloud-based services. We believe there is no substitute for client care, and are proud to be a nine-time winner of the Stevie Award for front-line customer service and a winner of the Better Business Bureau’s Torch Award for Marketplace Ethics, and to maintain a Net Promoter Score in the top five percent of our industry. Our Solutions: IT Services -Business Continuity -Disaster Recovery -Cloud Security -Managed IT Help Desk -Office 365 -Virtual CIO Infrastructure as a Service -UCaaS -Managed Networks, Servers, Firewall, Switches -Email security -Mobile Security Data Network Services -SD-WAN -MPLS & IP VPN -Private Line -Dedicated Internet Access -Integrated Voice & Data -Colocation Voice Services -PRI -POTS -SIP Trunking -Unified Communications -Contact Center/Call Center Please visit our website to learn more about how we can help your business grow and stay secure in an ever-changing world.

Access One

IT Solutions For Your Business - Managed IT, Cybersecurity, UCaaS, Data and Voice, and Security Systems

business technologyMobile SecurityMPLSManaged NetworktelecommunicationsSD WANManaged ITVOIPCall CenterHosted PBX

A

accessoneinc.com

51-200 employees

IT Services and IT Consulting

Chicago, IL

1993

Privately Held

7.8k LinkedIn followers

• 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.
• 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.
• 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.
• 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

• 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

• 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.

• 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.