Director, Sales Enablement

Ensono, LP; Downers Grove (IL); Hybrid; USD 156,000 - 210,000; Full time

Benefits offered by this job

Unlimited Paid Days Off

401k with company match

Education Reimbursement

Sabbatical leave

Wellness program

Job summary

Ensono is seeking a Director of Sales Enablement to build and lead the sales capability strategy for the Global Client Engagement organization. This leader partners with GCE to define capabilities, design curricula, and drive revenue growth.

The role blends executive-level planning with hands-on coaching of senior sellers and managers. The position leads a team to deliver role-based journeys, onboarding, ongoing training, certification, and coaching frameworks, while embedding AI fluency and

Qualifications

• 10+ years in Sales Enablement, L&D, Sales Operations, Revenue Operations, or Sales Leadership.
• Proven record of establishing successful Sales Learning Academies.
• Experience leading enterprise enablement strategy and teams.
• Ability to partner with sales orgs to improve capability and outcomes.
• Strong collaboration with senior stakeholders across functions.

Responsibilities

• Set the sales enablement strategy with GCE leadership and align to growth objectives.
• Identify capability gaps and prioritize enablement roadmap.
• Design and deliver role-based development journeys for Client Partners, BDRs, Sales Executives, Solution Architects, and Sales Leaders.
• Lead onboarding programs and learning paths to accelerate ramp time.
• Oversee training in consultative/value-based selling, negotiations, and account planning.
• Establish certification programs and proficiency assessments.
• Coach sales managers with frameworks and manager-led learning practices.
• Own the sales capability architecture and governance across GCE roles.
• Embed AI fluency into learning and enablement programs.
• Establish dashboards and KPIs to measure impact and drive improvements.

Skills

Sales Enablement

Sales Operations

Leadership

Analytical skills

Stakeholder Management

Executive communication

Tools

CRM systems

LMS platforms

Analytics tools

Job description

At Ensono, our Purpose is to be a relentless ally, disrupting the status quo and unleashing our clients to Do Great Things! We enable our clients to achieve key business outcomes that reshape how our world runs. As an expert technology adviser and managed service provider with cross-platform certifications, Ensono empowers our clients to keep up with continuous change and embrace innovation.

We can Do Great Things because we have great Associates. The Ensono Core Values unify our diverse talents and are woven into how we do business. These five traits are the key to achieving our purpose:

Honesty, Reliability, Curiosity, Collaboration, and Passion.

About the role and what you’ll be doing:

The Director, Sales Enablement builds and leads Ensono’s sales capability strategy in direct support of the Global Client Engagement (GCE) organization, improving seller effectiveness, accelerating onboarding, strengthening commercial skills, and driving revenue growth. Reporting to the VP, Global Organization Development with a dotted line to Sales Operations, this role is the link between learning strategy and commercial execution.

This is a player-coach leadership role. The Director partners with GCE leaders to set the strategic enablement agenda — what capabilities the sales organization needs and in what sequence — and leads a team to build and deliver it. While the team owns day-to-day execution, the Director is expected to stay close to the work and roll up their sleeves when it matters: facilitating high-visibility sessions, shaping critical curriculum, coaching senior sellers and managers directly, and stepping in to keep priority programs on track. Candidates must be equally credible in the executive planning conversation and in the room with sellers.

Key Responsibilities

Strategic Direction with GCE Leaders

• Set the sales enablement strategy jointly with GCE leadership, aligned to Ensono’s growth objectives and go-to-market priorities.
• Partner with GCE leaders to identify capability gaps, prioritize the enablement roadmap, and serve as trusted advisor on capability-building.
• Operate as a strategic performance consultant by identifying root causes of seller performance challenges and determining whether interventions should include learning, coaching, process improvement, manager reinforcement, sales tools, or organizational change initiatives.

Program Design & Delivery

• Direct the design of role-based development journeys for Client Partners, BDRs, Sales Executives, Solution Architects, and Sales Leaders, personally shaping and facilitating the highest-impact ones.
• Lead onboarding programs and learning paths that accelerate ramp time for new hires, promotions, and role transitions.
• Oversee ongoing training in consultative and value-based selling, executive conversations, account planning, negotiation, and solution positioning.
• Establish certification programs and capability assessments that verify seller readiness.
• Equip sales managers with coaching frameworks, standards, and manager-led learning practices, and coach senior leaders directly where it drives the most value.
• Own the sales capability architecture — building a sustainable Sales Academy and skills ecosystem — including proficiency models, skills frameworks, role-based learning journeys, capability assessments, certification programs, and sales academy governance that ensure consistent skill development across GCE roles.

AI Fluency & Go-to-Market Readiness

• Embed AI fluency into GCE learning: AI fundamentals in sales, data literacy, generative AI for proposals and messaging, AI-driven lead and opportunity management, predictive forecasting, client insights, and sales automation.
• Partner with AI University and skills intelligence teams to align role-specific AI skills, assessments, and proficiency expectations to GCE roles.
• Ensure the team delivers practical job aids, coaching guides, use-case libraries, and learning labs that help sellers use AI responsibly and effectively.

Performance Measurement

• Partner with Sales Operations to identify performance trends and prioritize initiatives.
• Establish dashboards and KPIs measuring enablement effectiveness and business impact.
• Use data to continuously improve programs; provide executive reporting on capability outcomes and productivity gains.
• Establish a measurement architecture linking enablement investments to business outcomes, including onboarding productivity, opportunity progression, forecast quality, speed-to-close, account growth readiness, manager coaching adoption, and sales productivity improvements.
• Build, develop, and lead a high-performing enablement team, setting clear priorities and standards.
• Balance delegation with hands-on involvement — empowering the team to own execution while remaining close enough to the work to unblock, quality-check, and step in when needed.
• Foster accountability, innovation, and continuous improvement.

We want all new Associates to succeed in their roles at Ensono. That’s why we’ve outlined the job requirements below. To be considered for this role, it’s important that you meet all Required Qualifications. If you do not meet all of the Preferred Qualifications, we still encourage you to apply.

Required Qualifications:

• 10+ years in Sales Enablement, L&D, Sales Operations, Revenue Operations, Commercial Excellence, or Sales Leadership.
• Proven record of having established successful and impactful Sales Learning Academies.
• Track record of setting enterprise enablement strategy and leading teams to execute it, with the depth to contribute directly when priorities demand.
• Demonstrated success partnering with sales organizations to improve capability, productivity, and business outcomes.
• Experience leading teams and influencing senior stakeholders across functions.
• Deep understanding of enterprise sales methodologies and commercial effectiveness practices.
• Expertise in learning design, adult learning principles, facilitation, coaching, and change management.
• Strong analytical and data-driven decision‑making skills.
• Proficiency with CRM, LMS, sales enablement technologies, and performance analytics tools.
• Excellent executive communication and stakeholder management; able to drive alignment without direct authority.

Preferred Qualifications:

• Technology services, managed services, cloud, consulting, SaaS, or B2B enterprise experience.
• Experience embedding AI fluency and AI‑enabled selling practices into sales enablement programs.

Why Ensono?

Ensono is a place to make better happen – for our clients and for your career. You can do great things through innovation or collaboration, by learning or volunteering, or to promote diversity and inclusion. You can do great things for your own health or for a healthier planet. Whatever it means to you to do great things we want Ensono to be the place you can do it.

We are a client‑facing business, but we do encourage clients to allow us to work remotely most of the time so if you are not required to be on a client site, you can choose to work from home or in our Ensono offices.

Some of our benefits include:

• Unlimited Paid Days Off
• Three health plan options
• 401k with company match
• Eligibility for dental, vision, short and long‑term disability, life and AD&D coverage, and flexible spending accounts
• Family Forming Benefit including fertility coverage and adoption/surrogacy reimbursement
• Paid childbearing and paternal leave
• Education Reimbursement, Student Loan Assistance or 529 College Funding
• Sabbatical leave
• Wellness program

As of the date of this posting, a good faith estimate of the current pay scale for this role is $155,557 to $210,212 annually based on a full‑time schedule. Please note that placement in the range may vary based on numerous factors including but not limited to skills, experience, internal equity, and business needs. In addition to base salary, other compensation programs, depending on eligibility, include an annual bonus plan based on company and individual performance, and an equity grant under our Associate Equity Appreciation Program.

Ensono is an Equal Opportunity/Affirmative Action employer. We are committed to providing equal employment to our Associates and building a diverse and inclusive workforce. All qualified applicants will be considered without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability, or other legally protected basis, in accordance with applicable law.

Pay transparency nondiscrimination statement/posting OFCCP’s pay transparency policy can be found on OFCCP’s website .

If you need accommodation at any point during the application or interview process, please let your recruiter know or email [emailprotected] .

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