Director of Sales Enablement

About Us

Sentinel delivers solutions that efficiently address a range of IT needs—from security, to communications, to systems & networks, to software applications, to cloud and managed services; all of which include staffing solutions for our clients. Since 1982, Sentinel has grown from providing technology maintenance services to becoming one of the leading IT services and solutions providers in the US. We have aligned with global technology leaders including Cisco, Dell, VMware, and Microsoft. Sentinel services customers both nationally and internationally with primary support operating centers in Downers Grove (HQ), Chicago, and Springfield, IL; Phoenix, AZ; Lansing, and Grand Rapids, MI; Milwaukee, WI; and Denver, CO.

Responsibilities

Sentinel Technologies is seeking a Director of Sales Enablement to design, implement, and continuously improve onboarding and development programs that accelerate new-hire productivity, shorten ramp time, and maximize sales performance across the organization. This role will work closely with sales, marketing, and operations leadership to establish clear performance standards, use data and modern AI tools such as Gong to identify capability gaps, and build a repeatable system for developing productive sales representatives.

• Onboarding: Design and build an onboarding program with clearly measurable milestones.
• Manager Training: Equip managers with the tools to coach and manage performance, manage expectations, and measure productivity.
• Sales Methodology: Implement a common sales methodology that will improve pipeline execution across the organization in all regions.
• Performance Analytics: Define baseline requirements for launching new programs, track adoption and business impact, implement best practices for ramp time, sales cycle, win rates, etc., and redesign programs that are not having an impact.
• Content and Tools: Determine the tech stack to best support rep development and reinforcement, as well as partnering with marketing for successful product launches.
• Strategic Leadership: Define and execute a comprehensive sales enablement roadmap tailored to a streamlined sales process that is aligned with the company’s growth objectives.

To be successful in this role, you must understand how the business makes money and prioritize work based on commercial impact, have diagnostic ability, turn broad priorities into clear measurable milestones, drive sustained behaviors while reinforcing accountability, create practical development paths, and balance quality with speed in building a program. This is a results-oriented role where success will be measured through improved new-hire outcomes and stronger rep performance—not training volume, content production, or program participation. This role will work onsite at our Downers Grove, IL headquarters.

Requirements

• 10+ years in B2B sales, enablement, revenue excellence, or another commercial role is required.
• 4+ years leading an enablement function in a scaling, multi-segment sales organization is required.
• Experience building or transforming an enablement function is required—not just operating one.
• Demonstrated success improving measurable sales outcomes such as ramp time, attainment, conversion, or win rate is required.
• Experience in implementing a successful sales methodology is required.
• Strong written and verbal communication, facilitation, and management skills are required.
• Must have a strong record of cross-functional partnership.
• Prior quota-carrying or frontline sales-management experience is preferred.
• Experience in a private equity-backed or performance-oriented environment is preferred.
• Experience supporting enterprise and mid-market sales motions is preferred.
• Familiarity with sales enablement, conversation intelligence, learning, and content-management platforms is preferred.
• Experience integrating teams, processes, or systems following acquisitions is preferred.
• Experience supporting a material go-to-market transformation is preferred.
• The candidate must have a car, as this position requires travel between locations and the transportation of equipment.
• A valid driver’s license and proof of vehicle insurance will be required.
• Legally authorized to work in the US without sponsorship.
• Must demonstrate a “can-do” attitude.
• We focus on candidates that display our “ACE” factor—Attitude, Compassion, and Enthusiasm to deliver quality solutions with exceptional customer service.

Pay

$180,000-$200,000 annual salary + bonus opportunity.

Benefits

• Medical, Dental, Vision
• 401K, 529
• Life Insurance
• Income Protection (Short and Long-Term Disability)
• Medical and Child/Elder Care Flexible Spending Account Plans
• Family Planning Benefits
• Financial Education
• Identity Theft Protection and Assistance
• Legal Services
• Employee Assistance Program
• Two weeks’ vacation, plus additional paid time-off for Personal and Sick leave
• Certification and hands-on training
• Employee discount for product services and entertainment