Come for the mission. Stay for the experience.

Let’s keep things simple: we are an unbelievably talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us - even you! 

Healthcare benefits are complex, underutilized and a mystery for most users. We’re removing that complexity. Now more than ever, employers are adding value to their employees’ benefits like telemedicine and mental health services. HealthJoy’s industry-changing tech platform consolidates those benefits into a simplified benefits experience, saving users time and money.  

With over $100M in fundraising to date, and the successful closing of our recent Series D, HealthJoy has garnered workplace awards for Inc.’s Fastest Growing Startups and Built In Chicago’s Best Places to Work while growing globally to nearly 400 team members. We’re continuing down the path of high growth and high impact, and this role is a key member of the Go-to-Market Teams making that happen.

Reporting to the Manager, Revenue Enablement, The Senior Revenue Enablement Specialist collaborates with cross-functional teams to execute revenue initiatives that align with company goals as they evolve. They work closely with sales, marketing and customer success managers to increase efficiency and productivity, enhance sales performance, and ultimately drive revenue and help managers grow their business. With ongoing support and coaching from their manager, this includes:

Your impact. 

• Lead the design, roll-out and optimization sales technologies like Highspot, Gong, and Outreach, and internal campaigns to support adoption and usage
• Design and implement enablement activities to influence NDR (net dollar retention) and Net New Revenue
• Regularly score and coach pre- and post-sales on Consultative Selling best practices using Gong and effective communication skills to promote positive behavior changes
• Develop regular sequences in Outreach to increase outbound conversion rates
• Monitor enablement-specific metrics (like time-to-ramp, time-to-value, content-to-opportunity, win/loss trends) to provide proactive and reactive sales support
• With autonomy, project manage large and time-sensitive request for proposals (RFPs) through an iterative process and assist with the maintenance of RFP software (Loopio)
• Design courses and sales playbooks, roll-out coaching plans for “everboarding” program to help ensure adoption of effective sales skills and behaviors
• Develop trainings, activities and internal campaigns to promote excellence in Consultative Selling sales methodology
• Develop learning content in online learning platform Udemy and monitor completion
• Project manage and help design fun, innovative and inspiring annual sales kick-offs
• Collect, interpret, and report on data with manager to inform programs and leadership
• Support the iterative sales onboarding programs and product training modules for pre- and post-sales, tailored to each sales role, help with scheduling, course creation, and tracking KPIs
• Identify and share opportunities for process improvement
• Project manage and fulfill the occasional sales request
• Assist with end-to-end evaluation of and feedback on sales programs
• Contribute to a “think-tank” and inventive culture within the larger Marketing Team

About You.

• 4-7 years of experience with sales training/enablement (previous sales or customer success experience is a plus)
• You know the difference between “task-based enablement” and “performance-based enablement” and embrace the latter
• Experience working in the benefits industry; broker experience is desirable
• Motivated self-starter who can multitask and manage multiple deadlines and is comfortable working independently
• Knowledge of sales metrics such as ramp, conversion, sales velocity, win rates, NDR, etc.
• You bring creativity and fun ways to train and engage revenue teams
• You thrive on solving problems and are often the first to suggest solutions
• Experience supporting both pre- and post-sales teams
• Appreciation for data and using it to gauge program effectiveness
• Proven experience confidently driving projects to completion
• You take pride and joy in the work you own, striving for quality at all stages of development from initial drafts to completion
• Comfortable in a fast-paced environment and working independently
• You have an interest in growing your career in Sales Enablement and enjoy ongoing mentorship, coaching and challenges from your manager to continuously grow
• Experience in a sales-facing role, enablement or comparable such as sales ops, RevOps analyst, sales support, product marketing
• Takes a vested interest