Director of B2B Marketing & Sales Enablement

About this role

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…