Director, Sales Enablement

CentralSquare; Chicago (IL); Remote; USD 120,000 - 180,000; Full time

Job summary

A leading enterprise software company seeks a Director of Sales Enablement to design and execute strategies that drive performance and productivity across Revenue functions. This role requires extensive experience in enablement and sales processes, with a focus on collaboration and content development for training initiatives.

Qualifications

• 5–10 years of success in sales enablement or related fields.
• Deep understanding of B2B/enterprise sales processes.
• Excellent communication skills and ability to influence.

Responsibilities

• Partner with Revenue Leadership to assess enablement needs.
• Lead onboarding programs to accelerate productivity.
• Manage and improve sales enablement programs using data.

Skills

Collaboration

Project Management

Communication

Facilitation

Tools

Microsoft Office Suite

Salesforce

LMS platforms

Sales enablement platforms

Job description

CentralSquare is a unique enterprise software company whose mission is to build safer, smarter, more connected communities.More than8,000 public sector agenciestrust CentralSquare solutions each and every day. We serve governments of all sizes, from small towns to major cities, to make delivering public services less costly and more efficient.

Director, Sales Enablement

Arizona (Remote)

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About CentralSquare Technologies

CentralSquare is a unique enterprise software company whose mission is to build safer, smarter, more connected communities.More than8,000 public sector agenciestrust CentralSquare solutions each and every day. We serve governments of all sizes, from small towns to major cities, to make delivering public services less costly and more efficient.

Job Description

The Director of Sales Enablement partners with Revenue Organization Leadership and Learning & Development to design and execute enablement strategies that drive quota attainment, accelerate ramp time, and support the execution of key go-to-market initiatives. This role oversees the development and delivery of onboarding and ongoing learning programs across all Revenue functions, enabling both individual contributor and leadership effectiveness. Reporting to the Vice President of Revenue Operations, the Director ensures that enablement efforts align with organizational goals and sales performance outcomes.

Job Duties:

• Partner with Revenue Leadership, cross-functional teams, and subject matter experts to assess enablement needs and prioritize high-impact initiatives.
• Design and lead onboarding programs for new Revenue Organization hires to accelerate time-to-productivity.
• Develop and deliver enablement content in multiple formats, including live workshops, virtual training, eLearning, and job aids.
• Manage and continuously improve sales enablement programs using data and feedback to ensure alignment with business goals.
• Measure learning outcomes and program effectiveness; report findings and adjust programs accordingly.
• Maintain an organized, up-to-date enablement content library that is easily accessible to the Revenue Team.
• Craft and distribute communications to promote alignment, training participation, and change readiness across the Revenue Organization.
• Perform additional duties as assigned to support Revenue Organization objectives.

Skills & Requirements

Required Qualifications:

• 5–10 years of proven success in sales enablement, sales training, or a related field.
• Deep understanding of B2B/enterprise sales processes, methodologies, and customer lifecycle.
• Demonstrated ability to collaborate with senior leadership and drive cross-functional initiatives.
• Proven project management skills with the ability to manage multiple initiatives simultaneously.
• Excellent written and verbal communication skills, with an emphasis on clarity and influence.
• Experience with adult learning theory, instructional design, and modern enablement platforms.
• Strong facilitation and coaching skills across live, virtual, and asynchronous formats.
• High degree of organization, attention to detail, and ability to work autonomously.
• Proficiency in Microsoft Office Suite and familiarity with tools such as Salesforce, LMS platforms, and sales enablement platforms.
• Willingness to travel up to 15%.