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Director of Sales Enablement

Sentinel


Job Location:

Downers Grove, IL - USA

Yearly Salary: USD 180000 - 200000
Posted: 26 August 2026 (28 days ago)
Application Deadline: 5 December 2026
Vacancies: 1 Vacancy

Job Summary

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. 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.

Core 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 companys growth objectives.
Qualifications
  • 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
  • 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 location and the transportation of equipment
  • A valid drivers 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.

Compensation:

$180000-$200000 annual salary bonus opportunity

What you get:

We offer an energetic work environment with many corporate culture amenities competitive salary and rich benefit plan including: Medical Denal 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 additional paid time-off for Personal and Sick certification and hands-on training and employee discount for product services and entertainment.

Overview

IT happen!

Sentinel Technologies Inc. has been rated a top workplace every year since 2012!

About Us:

Sentinel delivers solutions that can 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 our staffing solutions for our clients. Since 1982 Sentinel has grown from providing technology maintenance services to our current standing as one of the leading IT services and solutions provider in the US. We have aligned with many of todays 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.

If you are MOTIVATED you can make IT happen at Sentinel. Our commitment to our employees is to create a work environment that encourages creativity an entrepreneurial spirit fosters growth through certification and hands-on training and values a team-oriented culture with rewards based on impact!

If you share our passion about what technology can do and want to be part of a top workplace environment wed like to have you join our team. Learn more at

As part of Sentinels employment process candidates will be required to complete a background check. Only those who meet the minimum requirements will be contacted. No phone calls please.

Sentinel is proud to be an equal opportunity employer including disability and accordance with Title VII and state regulations all qualified applicants will receive consideration for employment without regard to race color religion age sex sexual orientation gender identity national origin marital status pregnancy genetics disability military veteran status or any other basis protected by law.

If you are an individual with a disability and need assistance in applying for a position please contact .

The Know Your Rights Poster is available here

EEO Policy Statement is available here.

Experience:

Director


About Company

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Sentinel Technologies proudly presents Fortis: a comprehensive portfolio of security services and solutions designed to proactively protect every aspect of your digital and physical environment. Our goal is to ensure your organization has the most effective tools to defend its systems ... View more

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