Lead, Revenue Enablement

We are seeking an exceptional enablement professional to join our team as the Lead, Revenue Enablement, where you will play a critical role in shaping the success of our Growth organization by equipping team members with the tools and training they need to excel. If you’re passionate about driving learning, facilitating impactful sessions, and working in a dynamic, fast-paced environment, this position is for you.

Reporting to the Manager of Revenue Enablement, you will collaborate closely with the entire Growth team and cross-functional stakeholders. As the Headway sales motion evolves, this role is pivotal in ensuring our team members are equipped with the necessary tools, knowledge, and skills to succeed. You will build Headway's continued education experiences for new Growth team members at varying levels, including our Provider Growth Associates (AEs), as well as any new sales-related teams we establish.

Key Responsibilities

• Facilitation Excellence: Bring top-tier facilitation skills to lead training sessions and drive attention, engagement, and adoption of enablement initiatives across the Growth organization.
• Drive Measurable Outcomes and Track Metrics: Establish and maintain a robust system to drive measurable outcomes by tracking key metrics related to learner engagement and effectiveness.
• Deliver Comprehensive Enablement Programs: Design and execute enablement programs that leverage multiple learning modalities, including pre-work, in-session activities, and post-session reinforcement, to create a true end-to-end learning experience.
• Develop Tailored Training Plans: Create and deliver an ongoing training program that includes large-group, small-group, and 1:1 coaching sessions.
• Develop Sales Playbooks and Leverage Sales Tools: Develop sales playbooks from 0-to-1 that encompass all aspects of our buyers and sales cycle.

Key Skills and Qualifications

• Strong Facilitation Skills: Proven ability to lead engaging and impactful training sessions that drive adoption and behavior change.
• Outcome-Oriented Program Design: Expertise in crafting end-to-end enablement programs with clear, measurable goals and deliverables.
• Adaptability: Comfortable navigating evolving sales motions and adjusting strategies to meet new challenges.
• Content Development Expertise: Skilled at creating and maintaining high-quality, actionable enablement resources, including playbooks, job aids, and training materials.

You Will Love This Role If:

• You have 4+ years of direct experience in Enablement and a strong understanding of what it takes to drive effective training programs.
• You have experience in a high-performance, startup-stage sales organization, where agility and innovation are key.
• You possess dynamic, engaging, and agile presentation and 1:1 coaching skills, with the ability to command a room and lead colleagues to moments of self-discovery while creating a safe environment for insightful feedback.
• You have a history of building cross-functional partnerships and alignment, contributing to a cohesive and collaborative work environment.

Compensation and Benefits:

The expected base pay range for this position is $89,760 - $132,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development