Head of Sales (B2B) (Remote)

Our secure, intuitive technology helps employers bring humanity, certainty, and efficiency to some of the most complex moments in the workplace. The Sales Enablement Manager is responsible for designing, developing, and executing the programs that help AbsenceSoft's go-to-market teams sell, onboard, train, and execute with consistency. The role owns core enablement and new-hire training, and works extensively in Highspot, AbsenceSoft's single system for sales content, owned by Product Marketing. This is a standalone, senior individual contributor role on the Revenue Operations team, reporting to the Director of Revenue Operations, with significant autonomy to build the enablement function.
Own and operationalize the core sales playbook covering the full deal cycle (prospecting, discovery, demo, negotiation, close), keeping it current as messaging and positioning evolve from Product Marketing and process evolves with Revenue Operations.
Analyze Gong call recordings to identify patterns from top performers and translate findings into scripts, snippets, and coaching content.
Assess and prioritize content and training needs across the sales organization based on call reviews, pipeline trends, and manager and sales representative feedback, in partnership with Product Marketing.
Design and manage a comprehensive onboarding program for new sales representatives, including ramp milestones, certification checkpoints, and manager sign-off criteria.
Build interactive curricula and continuous coaching modules for new and experienced sales representatives, grounded in the scripts, playbooks, and content housed in Highspot.
Run live training and coaching sessions in both group settings (kickoffs, ramp cohorts) and individual sessions with sales representatives and managers.
Partner with front-line sales managers to reinforce enablement in the flow of work, equipping them to coach on plays, scripts, and playbook so training sticks beyond the classroom.
Track ramp progress, certification completion, and time-to-productivity for new hires, adjusting programs based on data-driven insights.
Align enablement programs with go-to-market initiatives alongside Sales leadership, Revenue Operations, and Product Marketing.
Support sales kickoffs, quarterly business reviews, and off-site meetings with training content and facilitation.
3-6+ years in sales enablement, sales training, sales operations, or a related revenue-facing role in B2B SaaS.

• Track record of building sales content repositories, scripts/playbooks, or training programs without existing frameworks or infrastructure.
• Hands-on experience with Salesforce, Gong, and a sales enablement platform such as Highspot.
• Excellent documentation skills with ability to turn ambiguous input into clear playbooks, scripts, and training content.
• Familiarity with sales coaching and performance platforms such as Ambition or Fullcast.

Instructional design background or certification.
Strong facilitator and communicator, able to turn ambiguous input into clear, usable scripts, playbooks, and training content.
Data-informed, using call reviews, pipeline trends, and ramp metrics to prioritize content and training investments.
Collaborative across Sales, Revenue Operations, and Product Marketing, with the credibility to get manager and rep buy-in on new programs.
Lead with Innovation - We create meaningful change through intelligence, focus and passion. We embrace curiosity, data, and insight to shape the future of our industry. We listen, learn, and build a culture where diversity of thought and experience drives better solutions and smarter decisions.
Achieve Together - The customer fuels everything we do. Drive Outcome - Every action we take delivers measurable value to our teams, our customers, and the employees they support. We're remote-first and results driven. We offer comprehensive benefits, a performance-based bonus program, and equity opportunities - because when we grow, you should too.
Recharge and reconnect with flexible time off, paid holidays, and flexible leave programs designed to support every season of life.
We're building an inclusive culture where every voice is valued, collaboration is celebrated, and success is shared.

We're committed to building a team as diverse as the customers we serve. This position is also eligible for annual bonus.