Director of B2B Marketing & Sales Enablement

Job description

## 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: