Sales Enablement Specialist, Enterprise

About the role:

We’re looking for a hands-on sales enablement professional who enjoys creating, teaching, and making things work better. You’ll work alongside the Director of Sales Enablement, Enterprise to build and deliver virtual and onsite onboarding, ongoing training, sales technology education, and practical resources that help our enterprise sellers succeed.

You understand how enterprise sellers work, how complex buying decisions unfold, and what prepares sellers for effective customer conversations. You bring instructional design and facilitation skills, along with the creativity to make learning engaging, useful, and memorable.

We use AI, we love it, and we encourage you to explore what it can do. Bring your ideas, experiment with new approaches, and find ways to make the work easier and more effective. There’s room to build, test, learn, and improve, whether you’re creating an interactive learning experience or simplifying a recurring task.

Our business moves quickly, and our enablement needs to keep pace. As our products evolve, buyer needs change, and new technologies emerge, we adapt with purpose. You’ll help translate those developments into timely, accurate training and resources that keep our sellers prepared. We value speed, sound judgment, and quality in equal measure.

You’ll partner with the Director to set priorities, design programs, and identify improvements, then bring that work to life with sound judgment. As you learn our products, sellers, and business, you’ll take on greater responsibility and ownership of defined programs and workstreams.

What you’ll do

• Partner with the Director to develop, deliver, and improve enterprise sales onboarding, including learning paths, live sessions, self-paced content, practice activities, and readiness assessments.

• Facilitate both live virtual and onsite onboarding and training on products, positioning, sales processes, tools, and methodologies.

• Lead interactive discussions, roleplays, and practice exercises that reflect enterprise selling situations, adapting your approach to the audience and learning environment.

• Coordinate onboarding schedules, logistics, facilitator preparation, subject matter expert contributions, and new-hire communications.

• Track new-hire progress and work with the Director and sales managers to address learning gaps and reinforce skills.

• Support field training and sales events through preparation, facilitation, and follow-up.

• Translate sales priorities and skill gaps into workshops, self-paced learning, job aids, and assessments with clear objectives and practical application.

• Create and update presentations, playbooks, solution overviews, and other sales collateral in partnership with Marketing and Product Marketing.

• Translate complex product information into clear resources that help sellers prepare for and lead customer conversations.

• Support product launches and feature releases with training materials, communications, and reinforcement.

• Develop sales practice scenarios for discovery, pitches, objection handling, and competitive conversations, including AI-enabled roleplay.

• Deliver technology training through live demonstrations, guided practice, and practical resources that help sellers use our sales tools effectively.

• Maintain and organize enablement boards, the Notion hub, and supporting content libraries so sellers can find current, approved resources.

• Build and update learning content, assignments, and assessments in WorkRamp, and track completion.

• Identify content gaps, outdated materials, and access issues, and coordinate updates with the appropriate partners.

What you have

• 4+ years of relevant experience across sales enablement, learning and development, or instructional design, including direct sales enablement experience supporting onboarding or ongoing seller development.

• Experience supporting enterprise B2B sales teams, with an understanding of complex sales cycles, multiple buying stakeholders, and account strategy.

• Practical instructional design skills, with the ability to translate sales priorities and skill gaps into clear learning objectives, realistic practice, reinforcement, and assessments.

• Experience facilitating both live virtual and in-person onboarding and training

• Experience delivering technology or systems training through demonstrations and hands-on practice.

• Ability to use AI tools such as Claude or ChatGPT to develop content, improve workflows, and evaluate outputs for accuracy and usefulness.

• Proficiency in Google Workspace

• Experience creating learning materials and sales resources in collaboration with subject matter experts or cross-functional partners.

• Experience working with a learning management system, enablement platform, or knowledge hub.

• Strong writing, organization, and project coordination skills, with the ability to manage multiple deliverables, incorporate feedback, and meet commitments.

• Ability to travel up to 30% for onsite onboarding, field training, sales meetings, and enablement events.

Nice to have

• Experience in healthcare, health technology, or AI-powered solutions, including familiarity with EHRs, revenue cycle management, or clinical and administrative workflows.

• Experience helping build or expand onboarding and enablement programs.

• Familiarity with revenue enablement and how training, content, tools, and processes support customer acquisition and account growth.

• Ability to use Claude Code to build tools, automate recurring work, or improve enablement workflows.

• Experience with AI roleplay platforms, conversation intelligence, or sales readiness assessments.

• Familiarity with MEDDPICC, Challenger, Command of the Message, or comparable sales methodologies.

• Experience with tools in our technology stack: Salesforce, Outreach, Avoma, ZoomInfo, LinkedIn Sales Navigator, Notion, WorkRamp, Orum, and Claude.