Director of B2B Marketing & Sales Enablement

Role Overview

The Director of B2B Marketing and Sales Enablement will build and lead the enablement function that powers Health-E Commerce’s commercial growth across B2B and B2B2C channels. You will design the strategy, programs, content, and tools that make our sales and partner-facing teams the most credible, helpful experts in the FSA/HSA and pre-tax benefits space.

What You Will Do

Key responsibilities include enablement strategy & leadership, onboarding, training, and certifications, content, playbooks, and tools, sales process, methodology, and coaching, insights, analytics, and optimization, and cross-functional collaboration and GTM support.

Why It Might Be a Fit

The ideal candidate will have a minimum of 8+ years of experience in B2B or B2B2C sales enablement, commercial L&D, revenue operations, or closely related roles, with at least 4+ years leading teams, and experience in healthcare, health benefits, digital health, or closely related domains.

Requirements

• Minimum of 8+ years of experience in B2B or B2B2C sales enablement, commercial L&D, revenue operations, or closely related roles
• Experience in healthcare, health benefits, digital health, or closely related domains
• Track record building or scaling enablement in a high-growth, investor-backed environment
• Strong understanding of complex, multi-stakeholder sales cycles
• Demonstrated ability to design, implement, and measure end-to-end enablement programs
• Hands-on experience with modern sales and enablement tools
• Excellent communication, storytelling, and facilitation skills
• Strong analytical skills and fluency with data
• Experience in e-commerce, marketplace, or retail-adjacent environments
• Background in instructional design / learning experience design for adult learners
• Familiarity with AI-enabled tools for content creation, personalization, call analysis, and knowledge management
• Bachelor’s degree in Business, Marketing, Education, Healthcare Administration, or related field; MBA or relevant advanced degree a plus

Benefits

• Medical, Dental, Vision, and 401K with a company match
• Dependent Care, FSA & HSA accounts
• Paid Parental & Bonding Leave
• Flexible PTO & office closure on all major holidays
• Monthly wellness & internet reimbursements
• Professional development including certification support & leadership coaching
• Mental Health resources
• 100% remote within the United States