Sales Enablement Manager - Benepass

About Us

At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce.

Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.

Our Mission

Helping companies reimagine how companies take care of their people.

Team & Role

We’re looking for a Sales Enablement Manager to help our commercial team sell with greater confidence, consistency, and impact. You’ll turn our product knowledge, market insights, and sales strategy into practical resources and learning experiences that help the team move opportunities forward.

Our sales involve complex benefits decisions and multiple stakeholders, including employers, brokers, and consultants. You’ll help our team explain our value clearly to each audience, handle common objections, and connect our solutions to the outcomes buyers care about.

You’ll report to the Head of Sales and partner closely with the Director of Sales Operations. You’ll own sales readiness, content, and training; Sales Operations will remain a key partner on sales process, systems, reporting, and workflow.

What You'll Do

• Build and improve onboarding and ramp programs for new sales hires, including product, market, process, and selling skills.
• Create and maintain practical sales resources, such as discovery guides, talk tracks, pitch decks, one-pagers, FAQs, objection handling, case studies, and competitive guidance.
• Develop role- and audience-specific materials for conversations with employers, brokers, consultants, and other partners.
• Lead ongoing training and reinforcement on sales skills, product updates, messaging, competitive positioning, and sales process changes.
• Partner with the Head of Sales and frontline managers to identify skill gaps and focus enablement on current business priorities.
• Work with Marketing and Product to turn product capabilities, launches, and market changes into clear, accurate guidance for the field.
• Gather feedback from sellers and managers, and review customer conversations, win/loss themes, and deal outcomes to identify what the team needs.
• Coordinate with Sales Operations on CRM workflows, sales tools, process adoption, and reporting so that training and systems support one another.
• Organize sales content so the team can find the right, current resource quickly; establish a regular process for reviewing and updating it.
• Measure whether enablement is helping, using indicators such as ramp time, training completion, content use, rep confidence, process adoption, and relevant sales performance trends.

About You

• 3+ years of experience in sales enablement, sales training, sales, sales operations, product marketing, or a related commercial role.
• Experience supporting a B2B sales team with a consultative or multi-stakeholder sales process.
• Strong writing and presentation skills, with the ability to make complex products and ideas clear for different audiences.
• Experience creating sales materials and delivering training or coaching that sellers can use in real customer conversations.
• Strong project management skills and the ability to coordinate work across Sales, Marketing, Product, and Operations.
• A practical, feedback-driven approach to improving programs, content, and workflows.
• Familiarity with CRM and sales tools such as Salesforce, Gong, Seismic, or similar platforms.
• Experience in employee benefits, healthcare, HR technology, fintech, or another complex B2B solution is a plus.

How Success Will Be Measured

• New sales hires ramp effectively and understand our product, buyers, and sales process.
• Reps can explain our value clearly and adapt their approach to employers, brokers, and consultants.
• Sales resources are current, easy to find, and used in the field.
• Training and enablement programs improve targeted skills and support adoption of agreed sales practices.
• Field feedback and sales performance data lead to useful, visible improvements in enablement.

Compensation & Benefits

• Base Salary: $120,000 to $140,000 + equity
• 95% coverage of medical, dental, and vision insurance
• $250 one-time work-from-home setup stipend
• $500/year Learning & Development benefit
• $150/month cell phone and internet stipend
• $100/month Wellness benefit
• $100/month Co-working and Commuter benefit
• Flexible PTO
• Several team onsites per year