Director of Sales Enablement

Sentinel•Downers Grove, IL

1d•$180,000 - $200,000•Onsite

About The Position

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. 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 is required
Must have a strong record of cross-functional partnership
The candidate must have a car, as this position requires travel between location 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

Nice To Haves

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

Responsibilities

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 ultimately 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.