Sales Enablement Senior Manager

Hybrid | Chicago, IL | Full-Time | Excellent Benefits

Are you passionate about helping sales teams perform at their highest level? Do you enjoy creating impactful training programs, developing sales content, and equipping teams with the tools they need to win?

Labelmaster is seeking a Sales Enablement Senior Manager to support and strengthen our Sales and Customer Success organizations. In this newly created role, you will develop the content, training, and enablement programs that drive seller effectiveness, improve customer engagement, and accelerate revenue growth.
This is more than a traditional training role. You'll partner closely with Sales, Marketing, and Customer Success leaders to build onboarding programs, create seller playbooks, develop competitive messaging, and ensure our teams are prepared to effectively engage buyers throughout the customer journey.
We are an established and growing company that takes the complexity out of shipping Dangerous Goods (Hazmat), making the world a safer place.

What You'll Do

• Develop sales playbooks, battle cards, case studies, and competitive messaging
• Create and deliver onboarding and ongoing training programs
• Manage seller readiness, certifications, and product knowledge training
• Partner with Sales Leadership on coaching and skill development
• Gather field feedback and improve sales content and training initiatives
• Support Customer Success onboarding and enablement programs
• Maintain a centralized sales content library and resources hub

What We're Looking For

Required

• 3+ years of sales enablement, sales training, or related experience in a B2B environment
• Experience developing seller playbooks, battle cards, sales tools, and competitive content
• Experience designing and delivering sales onboarding and training programs
• Strong instructional design and content development skills
• Exceptional PowerPoint and presentation development capabilities
• Strong project management and organizational skills
• Excellent written and verbal communication skills
• Ability to collaborate effectively across multiple departments
• Proficiency with Adobe Creative Suite and Microsoft Office applications

Preferred

• Experience with sales enablement platforms such as Highspot, Seismic, or similar solutions
• Experience with Learning Management Systems (LMS)
• CRM experience, including Microsoft Dynamics 365 or equivalent platforms
• Video learning and e-learning authoring experience (Articulate, Camtasia, or similar)
• Experience in regulated industries
• Background supporting both Sales and Customer Success organizations

Why You'll Love Working Here

• Hybrid work schedule
• Competitive compensation ($125,000 - $135,000)
• Comprehensive health, dental, and vision benefits
• 401(k) with company match
• Paid holidays and generous PTO
• Professional development opportunities
• Collaborative and growth-focused culture
• Opportunity to build and shape a newly created strategic role
• Work directly with leadership to drive sales and customer success performance
• Join a stable, growing organization committed to innovation and safety

Who You Are

• Passionate about helping sales professionals succeed
• A confident trainer and facilitator who enjoys presenting to teams
• Collaborative, curious, and solutions-oriented
• Highly organized and detail-focused
• Adaptable and comfortable in a fast-paced environment
• Proactive in identifying opportunities and recommending improvements
• Customer-focused and committed to delivering business results

EEO Employer – Veterans and IWD are strongly encouraged to apply

Labelmaster is proud to be an Equal Employment Opportunity Employer and we are committed to the concept and practice of equal opportunity in all aspects of employment. It is our intent to comply with our duty to provide reasonable accommodations for qualified employees and applicants as required by law. All requests for accommodations should be made in writing to Jay Hollins by emailing

Pay Transparency Policy Statement - The contractor will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor's legal duty to furnish information.