About the role:

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.

You will operate as a player-coach: setting vision and standards, while also rolling up your sleeves to build programs, analyze impact, and refine based on data. You will lead a small, high-impact team that includes dedicated functions for training and learning experience design, events, and B2B marketing.

Key responsibilities:

Enablement Strategy & Leadership

• Define and own a multi-year sales enablement strategy aligned to Health-E Commerce's growth plan, sales team KPI’s, and channel strategy.
• Create the enablement playbook (what we do / don't do), operating model, intake, and prioritization framework for requests from Sales, Marketing, and Product.
• Build, lead, and develop a small but high-impact enablement team.
• Establish clear KPIs for enablement (ramp time, win rate, partner activation, sales cycle, content utilization, AOV, conversion lift) and report regularly to senior leadership

Onboarding, Training, and Certifications

• Design and own role-based onboarding for B2B Sale and partner success / account management.
• Build curricula that cover FSA/HSA and tax-advantaged health account fundamentals, Health-E Commerce product and brand portfolio, buyer personas and value messaging, and sales process and methodology.
• Implement a certification framework that validates both knowledge and field application and ties to manager coaching.

Content, Playbooks, and Tools

• Own the strategy, creation, and governance of sales and partner-facing content: messaging frameworks, pitch decks, one-pagers, solution overviews; vertical/segment playbooks for TPA’s- benefits admins, employers, payers, and brands; discovery guides, talk tracks, objection-handling guides, email templates; ROI/value calculators; competitive analysis and case studies and proof points.
• Ensure all content is accurate, compliant, and consistent with brand standards across Health-E Commerce, FSA Store®, HSA Store®, Patiently and Caring Mill.
• Define "what good looks like" for usage and embed content directly into seller workflows (working with B2B2C marketing to maintain consistency).

Sales Process, Methodology, and Coaching

• Partner with Sales to standardize sales processes for different motions (new partners, new integrations, new products etc.).
• Integrate chosen sales methodology into pipeline reviews, QBR calls, and deal strategy sessions.
• Enable front-line managers with coaching frameworks, scorecards, and call-listening guides.
• Use call recordings, win/loss analysis, and field feedback to continuously refine process and coaching.

Insights, Analytics, and Optimization

• Partner with business intelligence / finance to link enablement programs to commercial outcomes: new partner acquisition, activation, and revenue; cross-sell/upsell of new categories and brands; utilization and repeat-purchase behavior.
• Maintain dashboards and reporting that show training and certification completion, content engagement and effectiveness, and pre/post-program performance trends.
• Conduct regular field listening (roundtables, interviews, surveys) to understand where sales and partner teams are winning, losing, or getting blocked, and feed insights into the enablement roadmap.

Cross-Functional Collaboration and GTM Support

• Collaborate with Marketing on partner launch kits and campaigns, co-branded materials, and benefit education content for employers and members.
• Work with Product and Category Management to translate new offerings into compelling sales narratives and use cases, and equip sellers with "why this matters now" stories for each release.
• Support big rocks (e.g., new benefits admin partnerships, platform integrations, major category launches) with focused enablement sprints.
• Lead and develop the Marketing Manager, Events & B2B Marketing, ensuring field activations, partner-facing social and content strategy, and the partner feedback program are tightly integrated with the broader enablement roadmap.
• Lead and develop the Senior Manager, Training & LXD, ensuring learning experience design, internal training content, and partner-facing materials are aligned to sales priorities and continuously improving.

What you'll need:

• 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.
• Experience in healthcare, health benefits, digital health, or closely related domains (e.g., HSAs/FSAs, benefits administration, employer benefits).
• Track record building or scaling enablement in a high-growth, investor-backed environment (PE or VC), with demonstrable impact on sales productivity and revenue.
• Strong understanding of complex, multi-stakeholder sales cycles (e.g., employers, TPAs, payers, HR and finance leaders, procurement).
• Demonstrated ability to design, implement, and measure end-to-end enablement programs (onboarding, ongoing training, certifications, manager coaching).
• Hands-on experience with modern sales and enablement tools (CRM, LMS/LXP, content management, sales engagement, conversation intelligence).
• Excellent communication, storytelling, and facilitation skills; able to translate regulatory/tax and product complexity into simple, compelling value propositions.
• Strong analytical skills and fluency with data; comfortable working with business intelligence and Finance to tie enablement initiatives to business outcomes.
• Experience in e-commerce, marketplace, or retail-adjacent environments with a focus on category management and enablement.
• 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.

Core Competencies

• Strategic, systems-level thinking with a strong bias to action.
• Leadership and talent development in lean, high-ownership teams.
• Customer, partner, and consumer-centric mindset rooted in empathy.
• Operational excellence and project management rigor.
• Change management and stakeholder influence from front-line to C-suite.
• Continuous improvement orientation and comfort with experimentation.

Travel

Willingness to travel periodically up to 10% for partner meetings, field observations, sales kickoffs, and leadership offsites.

Note for Current Employees:

Please use the internal job board in Greenhouse to apply. Applications submitted through this external link will not be tagged as internal.

Compensation, Benefits, & Additional Details:

Health-E Commerce's compensation philosophy is grounded in market data and internal equity to ensure fairness and consistency across the team. Individuals new to the company should generally expect offers to fall between the entry point and midpoint of the salary range. Our goal is to provide an offer that supports growth potential within the role and allows for future salary progression.

• Compensation: $130,000 - 160,000
• Discretionary Annual Bonus Eligibility: Up to 20%
• 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
• Must be able to work EST hours

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