Enablement Director

A strong product. Three customer-facing teams. Scale the enablement that connects them.

Hi there!

We’re Sweed, a product-driven company building an all-in-one cannabis retail platform. We’re looking for an Enablement Director to help our Sales, Customer Experience (CX), and Support teams understand our product, communicate its value, and put that knowledge into practice.

You’ll own onboarding and ongoing enablement across all three teams. You’ll develop role-specific training, turn product updates into practical materials, and use real customer conversations to identify where people need support.

This is a hands-on leadership role with ownership of the function and significant autonomy over how it develops. You’ll set priorities, create content, deliver training, and strengthen programs that improve how our teams work with customers.

About Sweed

At Sweed, we’re reimagining how cannabis retailers operate. Our enterprise-grade platform combines POS, eCommerce, Marketing, Analytics, and Inventory Management into a single, seamless solution—eliminating the need for multiple third-party tools.

We build for simplicity, scalability, and performance, making life easier for cannabis retailers while helping them grow their businesses.

Our mission

We believe cannabis retailers deserve technology that makes running their businesses easier and serves their customers better.

The industry is evolving rapidly. We’re here to support that growth by making cannabis retail more efficient, accessible, and customer-friendly.

Where we are today

We’ve been on the market for seven years, continuously growing and refining our product. Our focus is on earning customer trust through better delivery, new capabilities, and a platform built for the complexities of cannabis retail.

As we grow, we’re bringing enablement across Sales, CX, and Support under one owner. We have existing tools, content, onboarding, and certification programs to build on. Your opportunity is to connect those pieces, address gaps, and establish consistent standards for learning and readiness across the organization.

The team and your role

We’re a global team of over 250 people. Our development organization operates in cross-functional product teams, while our CEO and Customer Experience team are based in the United States.

You’ll report to the VP of Growth & RevOps and work closely with Sales, CX, Support, Product, and Product Marketing. You’ll lead the enablement function, coordinate existing onboarding resources, and partner with managers to turn assessment findings into practical coaching.

This is a full-time, remote, US-based position. Eastern or Central time is preferred to support close collaboration with our teams. Occasional travel may be needed for customer visits, industry events, or team collaboration.

What you’ll own

• Onboarding & Ramp — Own onboarding from day one through readiness to work independently. Build role-specific plans for Sales, CX, and Support, with clear milestones, assessments, and realistic ramp expectations. Cover product knowledge, customer communication, workflows, and the tools each role uses, including HubSpot and Gong.

• Product Education & Value Messaging — Partner with Product and Product Marketing to translate releases into clear customer value and practical guidance for each team. Run briefings, demos, and deep dives, and keep messaging, FAQs, and demo guidance current.

• Sales Enablement — Create and maintain playbooks, talk tracks, videos, and practical 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 as they launch.

• Customer Experience Enablement — Develop role-specific training for account management, customer success, and customer service within the CX team. Equip people to support adoption, renewals, and expansion, manage customer expectations, and reinforce value messaging throughout the customer relationship.

• Support Enablement — Build training and resources for product knowledge, troubleshooting, escalation paths, and customer communication. Partner with Support leaders to turn recurring issues into targeted education and share customer feedback with Product and other customer-facing teams.

• Certification & Assessment — Scale, extend, and enforce existing role-specific certification programs and scorecards that define what good performance looks like. Establish regular assessments and give managers clear evidence of where employees need coaching or further training.

• Gong & Coaching Insights — Configure and use Gong playbooks, scorecards, and reporting to assess real conversations. Identify recurring gaps, share specific coaching priorities with managers, and track whether training changes behavior.

• LMS Ownership — Evaluate learning management system (LMS) platforms against our internal and customer education needs and recommend the right approach. Build out the selected platform’s course structure, learning paths, assessments, and reporting, then launch and manage learning programs within it. Own ongoing administration, adoption, and improvements.

• Learning Content — Personally create and maintain courses, playbooks, videos, quizzes, and certifications. Keep content current as products and processes change, retire outdated materials, and use LMS completion and assessment data to follow up with managers on learning gaps.

• Cross-Functional Alignment — Establish a regular education cadence with Product and customer-facing leaders. Bring field feedback back to Product, make ownership clear, and measure the results of enablement programs with RevOps and team managers.

What success looks like

Your first priority will be to understand how our teams work, assess existing programs, and identify where enablement needs to improve.

During your first three months, you’ll be expected to:

• Assess onboarding, training, content, and learning needs across Sales, CX, and Support.

• Agree on priorities and measurable outcomes with RevOps and team leaders.

• Extend existing certification programs and scorecards, clarify standards, and establish a regular assessment cadence.

• Begin closing the highest-priority gaps through practical training and playbooks.

• Establish a consistent process for product education and release communication.

• Evaluate our current LMS capabilities and recommend a plan for the platform, learning paths, and reporting.

• Put a clear plan in place to improve role-specific onboarding and reinforce certification requirements.

As these foundations develop, we’ll expect measurable improvements in employee readiness, ramp time, and the quality of customer conversations. You’ll work with leaders to connect these improvements to relevant sales and customer outcomes.

What you bring

• B2B SaaS Enablement Experience — Experience building and scaling enablement programs in a B2B SaaS organization, with a clear understanding of how software is sold, adopted, and supported.

• Experience Across Sales, CX & Support — A track record of adapting training and materials for different customer-facing roles and their distinct responsibilities and workflows.

• Experience Building from Scratch — Evidence that you have personally built onboarding, training, playbooks, or certification programs and put them into use.

• LMS Experience — Hands-on experience evaluating LMS platforms, building out their structure and functionality, and launching and managing learning programs within them. You can translate learning needs into platform requirements, configure courses, learning paths, assessments, and reporting, and drive adoption.

• Hands-On Content Creation — Strong writing and facilitation skills, with experience personally creating useful materials and delivering training.

• Certification & Ramp Design — Experience defining readiness standards, developing practical assessments, scaling certification programs, and setting realistic expectations for time to productivity.

• Gong Proficiency — Hands-on experience using Gong for call analysis, scorecards, playbooks, and reporting, and translating findings into coaching priorities.

• Product Value Translation — The ability to explain technical features in terms of customer problems, use cases, and business value.

• Measurement & Follow-Through — Specific examples of how your programs changed behavior or improved results, supported by clear metrics.

• Cross-Functional Leadership — The ability to align stakeholders, make priorities clear, and move work forward across departments.

• Comfort with Building and Change — You can set direction and deliver the work yourself, using existing resources while improving how things are done.

Cannabis industry experience is not required. Curiosity about our customers and the ability to learn a complex product are essential.

How you work

• Ownership — You follow through on commitments, surface blockers early, and take responsibility for delivery.

• Practical Thinking — You build training and tools people can apply in their daily work.

• Customer Focus — You listen to customer conversations and connect learning to real customer needs.

• Adaptability — You adjust programs when evidence shows that something is not working.

• Clear Communication — You make complex information understandable and keep teams aligned on expectations.

What we offer

• Competitive compensation.

• Medical, dental, vision, and additional health insurance options.

• Paid parental leave.

• Generous PTO and paid company-observed holidays.

• A remote work environment with occasional travel.

• Ownership of enablement across three customer-facing teams, with significant autonomy over program design and structure.

• Close collaboration with leadership, Product, and RevOps, with a direct opportunity to see your work improve team performance.

Our interview process

1. Recruiter Call — Discuss your experience, expectations, and interest in the role, and learn more about Sweed.

2. Interview with our VP of Growth & RevOps — Explore the programs you’ve personally built and scaled, your approach to Sales enablement, and how you measure results.

3. Interview with the VP of CS — Discuss CX and Support enablement, product education, LMS experience, and how you would address the needs of different customer-facing roles.