Director of Sales Enablement

Sentinel

$180K — $200K *
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years in B2B sales, enablement, or revenue excellence required.
  • 4+ years leading an enablement function in a scaling organization required.
  • Experience in building or transforming an enablement function is essential.
  • Demonstrated success in improving measurable sales outcomes required.
  • Experience in implementing a successful sales methodology is required.
  • Strong communication and management skills are essential.
  • Cross-functional partnership experience is a must.

Responsibilities

  • Design an onboarding program with measurable milestones.
  • Equip managers with coaching tools to enhance performance.
  • Implement a common sales methodology to improve pipeline execution across all regions.
  • Define baseline metrics for new programs, tracking business impact and adoption.
  • Determine the tech stack to support rep development and marketing collaboration.
  • Execute a sales enablement roadmap aligned with company growth objectives.

Benefits

  • Energetic work environment with corporate culture amenities.
  • Comprehensive health benefits including medical, dental, and vision.
  • 401K and 529 plans to support financial growth.
  • Life insurance and income protection options available.
  • Short and long-term disability coverage included.
  • Flexible spending accounts for health and childcare expenses offered.
  • Paid time off for vacation, personal, and sick leave, plus additional training.
Full Job Description
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 company's 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 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.

Compensation:

$180,000-$200,000 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

MOTIVATED.....make IT happen!

Similar Jobs

More Jobs at Sentinel

More Business Services Jobs

Find similar Director of Sales Enablement jobs: