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 preferred; 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 in building the Enablement function with manager’s direction and protecting its reputation as a strategic partner to Sales
• Excellent interpretation skills to build rapport within Sales, Customer Success and other stakeholders throughout the business
• Strong communication skills

Total Rewards 

Job Level: 30 

Target Base Compensation Range for Job Level: $80,000 - 100,000

The cash compensation above includes base salary only. Certain roles are eligible for additional cash incentives such as commission, annual bonus targets, overtime pay or other variable incentives.

HealthJoy maintains a comprehensive strategy to determine rewarding and competitive packages for individual compensation for new hires, internal promotions and internal job changes. This strategy is based on several factors unique to each individual, including: 1) the skills, experience and qualifications of the individual; 2) the responsibilities and demands of the role; 3) analysis of external market data; and 4) company budget and financial performance. 

HealthJoy is a remote-first employer. The disclosed range estimate has not been adjusted for the applicable geographic differential associated with the location at which the position may be filled. 

At HealthJoy, it is not typical for an individual to be hired at or near the top of the range for their role, and compensation decisions are dependent on the facts and circumstances of each role and individual. 

In addition to cash compensation, HealthJoy offers a rich “Total Rewards” package that includes:

• Medical, Dental and vision insurance packages
• HSA contribution match
• Stock options for eligible roles
• 401k match
• Paid parental leave
• Company sponsored Short Term and Long Term Disability coverage
• Flexible PTO 

Commitment to Equal Pay

At HealthJoy, we are committed to creating a diverse and inclusive workplace where everyone has the opportunity to succeed and thrive.

We believe that everyone should be paid based on their qualifications, experience, and the work that they do, and not on their gender, race, or any other personal characteristic. Our compensation practices are essential to fostering a diverse and inclusive culture where we value the contributions of all our employees. 

We conduct thorough annual reviews of employee pay and our pay practices to ensure we reward the right behaviors and are providing equal pay for equal work. 

Additionally, we assess the external market and internal equity across like roles. As part of our regular review of pay practices, HealthJoy examines employee pay for potential disparities between persons of different genders, races and ethnicities that are not explainable by objective factors such as performance, experience level, credentials, or location, and are committed to correcting any issues and reviewing practices from unintended outcomes.