Sr Sales Enablement Specialist

The Senior Sales Enablement Specialist is a senior individual contributor responsible for defining learning and enablement strategy at the program level and owning the development, execution, and measurement of assigned sales enablement programs. Reporting to the Sr. Director of Learning & Enablement, this role serves as a primary enablement partner to the Sales organization, and a central coordination point across cross‑functional enablement efforts.

In addition to program ownership, the role functions as a coordination, visibility, and consultative hub for sales enablement. The Senior Sales Enablement Specialist maintains awareness of enablement activities occurring across Sales, Services, Marketing, Product Marketing, and related teams, and helps bring those efforts together into cohesive, well‑timed, seller‑ready experiences. This role plays a critical part in reducing duplication, improving sequencing, and ensuring enablement efforts gain the adoption and traction required to drive impact.

What We Do

We calm the confusion of IT by guiding the connection between people and technology. If a customer is looking for a better way to manage their warehouse inventory, equip their workforce, or secure their data, we make it happen. All it takes is finding the right combination of tech hardware, software, cloud solutions, and support services. That’s what we do. We’re the IT Department’s IT Department.

Who We Are

Our team is made stronger by a multitude of backgrounds, experiences, and perspectives. It’s what makes Connection unique—what drives us to innovate and create technology solutions that stand apart from the crowd. We’d love for you to be a part of that fabric, to share your ideas and experiences with a team that thrives on fresh thinking, creativity, and helping others.

Why You Should Join Us

You’ll find supportive teammates and a rewarding career at Connection—plus great benefits. We take pride in supporting employees with a total rewards package that provides financial, emotional, and physical resources for you and your family.  Our compensation, 401k plans, medical insurance, and other benefits are progressive and competitive.  We value the importance of our employees’ emotional wellbeing. To support employees, we provide free therapy visits, mental health coaching and tools, and meditation resources. You’ll also enjoy a generous paid time off package that includes not only vacation and care time, but also Wellness and Volunteer Time Off days. 

Because of the possibility for fraudulent job postings on many popular job boards, please be advised that Connection will never offer a position of employment without a complete interview process and communication with a “live person".  

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa at this time.

Enablement Program Strategy and Ownership

• Define the learning and enablement strategy at the program level (e.g., onboarding, role readiness, solution enablement, sales plays, continuous development).
• Conduct needs analysis to identify performance gaps and enablement requirements for specific sales audiences.
• Design program‑level learning strategies that clearly define:
• Target outcomes and success criteria
• Learning objectives and skill focus
• Delivery modalities (live, virtual, self‑paced, on‑the‑job)
• Reinforcement and sustainment approach
• Align program strategies with sales priorities and the broader learning direction set by the Sr. Director of Learning & Enablement

Program Development, Execution, and Measurement

• Own assigned sales enablement programs end‑to‑end, from design through delivery, reinforcement, and evaluation.
• Develop enablement content and learning experiences, including playbooks, job aids, talk tracks, workshops, certifications, and supporting resources.
• Facilitate live and virtual enablement sessions, role plays, and workshops.
• Define and track program‑specific success metrics (e.g., readiness indicators, skill adoption, learner feedback).
• Measure not only participation and completion, but also adoption and field application, and continuously improve programs based on data and feedback.

Enablement Intake, Governance, and Consultation

• Act as the primary point for sales enablement and training efforts that impact the sales organization.
• Evaluates enablement requests to ensure alignment with sales priorities, audience readiness, and existing enablement initiatives.
• Determine appropriate timing, sequencing, and modality for enablement efforts to avoid overlap, duplication, and seller overload.
• Serve as a learning and enablement consultant to cross‑functional partners (e.g., Marketing, Product Marketing, Services) by advising on:
• Whether enablement or training is needed
• The most effective learning approach
• Appropriate delivery, reinforcement, and rollout methods
• Recommend approval, consolidation, delay, redesign, or denial of enablement efforts when necessary to protect seller focus and improve impact.
• Ensure enablement initiatives meet defined readiness and quality standards prior to deployment.

Sales Content and Field Readiness

• Ensure enablement content is seller‑ready, role‑specific, current, and easy to find.
• Partner with Services, Product Marketing, Marketing, and Services to translate launches, updates, and initiatives into actionable sales enablement.
• Support consistent messaging and application across programs and enablement touchpoints.

• 8+ years of experience in sales enablement
• Demonstrated experience owning enablement programs from strategy and design through execution and measurement.
• Experience supporting complex, solution‑based sales organizations.
• Strong facilitation, communication, and stakeholder management skills.
• Experience with enablement technologies (e.g., LMS, CRM, CMS, sales readiness platforms).
• Ability to analyze data and provide feedback to guide decisions and continuous improvement.
• Comfort making prioritization and timing decisions in service of seller focus and enablement effectiveness.
• Demonstrated experience enabling and reinforcing sales methodologies (e.g., Solution Selling, Challenger, MEDDICC, SPIN), including translating methodologies into seller behaviors, conversations, tooling, and reinforcement.