Enablement Director

Sweed

22h • Remote

About The Position

Sweed is seeking an Enablement Director to own onboarding and ongoing enablement for its Sales, Customer Experience (CX), and Support teams. This hands-on leadership role will connect and improve existing tools, content, onboarding, and certification programs, establish consistent learning and readiness standards, and develop the enablement function with significant autonomy.

The role includes designing role-specific onboarding and training; translating product releases into customer value messaging and practical guidance; creating Sales, CX, and Support resources; extending certification and assessment programs; using Gong conversation insights to guide coaching; and evaluating, launching, and managing an LMS. The Enablement Director will create and maintain learning content, collaborate with Product, Product Marketing, RevOps, and customer-facing leaders, and measure program results through employee readiness, ramp time, conversation quality, and related sales and customer outcomes.

This is a full-time, remote, US-based position. Eastern or Central time is preferred. Occasional travel may be needed for customer visits, industry events, or team collaboration. The role reports to the VP of Growth & RevOps.

Requirements

• Experience building and scaling enablement programs in a B2B SaaS organization, with an understanding of how software is sold, adopted, and supported.
• Track record adapting training and materials for Sales, CX, and Support roles and their distinct responsibilities and workflows.
• Evidence of personally building and implementing onboarding, training, playbooks, or certification programs.
• Hands-on experience evaluating LMS platforms, configuring courses, learning paths, assessments, and reporting, and launching, managing, and driving adoption of learning programs.
• Strong writing and facilitation skills, with experience personally creating useful learning materials and delivering training.
• Experience defining readiness standards, developing practical assessments, scaling certification programs, and setting realistic time-to-productivity expectations.
• Hands-on Gong experience with call analysis, scorecards, playbooks, and reporting, and the ability to turn findings into coaching priorities.
• Ability to explain technical features in terms of customer problems, use cases, and business value.
• Specific examples of programs changing behavior or improving results, supported by clear metrics.
• Ability to align stakeholders, clarify priorities, and move work forward across departments.
• Ability to set direction and deliver work personally while using existing resources and improving how things are done.
• Ownership, including following through on commitments, surfacing blockers early, and taking responsibility for delivery.
• Practical thinking and ability to build training and tools people can apply in daily work.
• Customer focus and ability to connect learning to real customer needs through customer conversations.
• Adaptability to adjust programs when evidence indicates they are not working.
• Clear communication and ability to make complex information understandable and keep teams aligned.
• Curiosity about customers and ability to learn a complex product.
• Cannabis industry experience is not required.

Responsibilities

• Own onboarding from the first day through readiness to work independently for Sales, CX, and Support, including role-specific plans, milestones, assessments, and ramp expectations.
• Develop training covering product knowledge, customer communication, workflows, and role-specific tools, including HubSpot and Gong.
• Partner with Product and Product Marketing to translate releases into customer value and practical guidance; run briefings, demos, and deep dives; and maintain messaging, FAQs, and demo guidance.
• Create and maintain Sales playbooks, talk tracks, videos, and tools for discovery, demos, objection handling, competitive positioning, negotiation, and closing; adapt materials for SMB, Mid-Market, and Enterprise sellers and support new sales motions.
• Develop role-specific CX training for account management, customer success, and customer service, supporting adoption, renewals, expansion, expectation management, and value messaging.
• Build Support training and resources for product knowledge, troubleshooting, escalations, and customer communication; use recurring issues to target education and share customer feedback with Product and other customer-facing teams.
• Extend and enforce role-specific certification programs and scorecards; establish regular assessments and provide managers with evidence of coaching and training needs.
• Configure and use Gong playbooks, scorecards, and reporting to assess customer conversations, identify gaps, recommend coaching priorities, and track behavior changes.
• Evaluate LMS platforms against internal and customer education needs, recommend an approach, and build, launch, administer, and improve the selected platform’s course structure, learning paths, assessments, reporting, and programs.
• Personally create and maintain courses, playbooks, videos, quizzes, and certifications; keep content current, retire outdated materials, and use learning data to follow up on gaps with managers.
• Establish a regular education cadence with Product and customer-facing leaders; bring field feedback to Product, clarify ownership, and measure enablement outcomes with RevOps and team managers.
• Assess existing programs and needs, agree on priorities and measurable outcomes with RevOps and team leaders, and address high-priority gaps through training and playbooks.
• Establish a consistent product education and release communication process and a plan to improve role-specific onboarding and certification requirements.
• Work with leaders to connect improvements in employee readiness, ramp time, and customer conversation quality to relevant sales and customer outcomes.

Benefits

• Medical, dental, vision, and additional health insurance options.
• Paid parental leave.
• Generous PTO and paid company-observed holidays.
• Remote work environment with occasional travel.
• Competitive compensation.
• Ownership of enablement across three customer-facing teams, with significant autonomy over program design and structure.
• Close collaboration with leadership, Product, and RevOps, with the opportunity to see work improve team performance.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed