Customer Success Manager

HealthJoy•Chicago, IL

13d•Remote

About The Position

Let’s keep things simple: we’re a talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us. Our path to success is paved with our proprietary technology, demanding team members who are naturally AI-forward and data-driven to accelerate our impact. Healthcare benefits are complex, underutilized, and a mystery for most people. That’s why it’s our vision to remove the complexity from being healthy and well. HealthJoy guides employees to affordable, high-quality healthcare by consolidating our clients’ health and wellness strategies into the HealthJoy Benefits OS - a simple, unified digital experience. This leads to healthier employees and a healthier bottom line. With over $100M in fundraising to date, HealthJoy has garnered workplace awards for Inc.'s Fastest Growing Startups and Built In Chicago’s Best Places to Work while growing globally to over 300 team members. We’re continuing down the path of high growth and high impact, and this role is a key member of the Customer Success team making that happen. Your impact. HealthJoy’s Customer Success Team is leading the charge at HealthJoy to deliver industry-leading outcomes to our customers, with the ultimate goal of driving customer retention and growth. As a Customer Success Manager, you’ll lead a designated book of business aligned to HealthJoy’s most strategic broker partners This is a unique opportunity for a high-energy benefits industry professional who is passionate about delivering customer value, and excited to pivot to a dynamic, fast-paced environment. You will be a key driver of HealthJoy’s revenue goals through proactive account management, strategic expansion, and world-class retention efforts.

Requirements

Benefits experience required. Experience working directly as an HR team member and/or as a benefit consultant is a great background for this role!
Minimum 4-5 years of customer-facing account leadership or related experience demonstrating a high degree of skill in serving as a trusted advisor.
Strategic and results-oriented approach to partnering with customers at all levels of an organization (individual contributor through C-Suite) to achieve desired outcomes.
Demonstrated success managing customer retention and account growth within a book of business, or related experience negotiating contracts that would demonstrate proficiency managing commercial negotiations with limited oversight.
Commercial Acumen: Proven ability to navigate a sales process, including overcoming objections, managing procurement/legal hurdles, and a "hunter" mindset for identifying expansion opportunities within a "farmer" role.
Highly collaborative and influential with your teammates and business partners across the organization to drive results and innovation.
Exceptional executive presence and ability to present complex or detailed information in a digestible and actionable manner.
Willingness to travel approximately 15-20% to support client book of business, as well as at a minimum quarterly to Chicago headquarters for internal team meetings as needed. We encourage local team members to come into the office on Wednesdays for shared work and collaboration time.

Responsibilities

Strategic Book Management: Confidently and independently own key outcomes for your book of business, including product adoption, utilization, Net Dollar Retention (NDR), and overall customer health.
Full-Cycle Revenue Ownership: Lead the end-to-end renewal and expansion sales process. You will identify, negotiate, and close upsell opportunities by aligning HealthJoy’s marketplace solutions with customer needs.
Sales Cycle Execution: Demonstrate mastery of the full sales cycle within your book of business. You will partner with Product Solutions Consultants and other senior leaders to conduct deep discovery to uncover pain points, map those challenges to HealthJoy solutions, and move deals forward by confidently asking for the close and defining clear, actionable next steps.
Executive Presence: Build strong, consultative relationships across all levels of a customer organization—from day-to-day champions to C-Suite stakeholders. You must be comfortable having direct, high-stakes conversations to drive alignment and value.
Crisis Management & Poise: Act as the primary external point of contact for escalations. You remain poised under pressure, resolving complex issues with a sense of urgency and a calm, solution-oriented mindset.
Strategic Advisement: Serve as main point of contact for your customers on strategies to optimize adoption across their members, drawing upon your extensive knowledge of HealthJoy’s product and services, benefit industry domain knowledge, and best practices; and partner effectively with HealthJoy’s Product Solution Consultant team to effectively position marketplace solutions and ultimately expand account value;
Data-Driven Leadership: Leverage AI (Claude, Gemini) and best-in-class software to proactively dive deep into the performance across your book of business, enabling you not only to provide better thought leadership to your book of business, but also socialize the voice of your customers across internal HealthJoy stakeholders.
Meticulous Execution: Maintain a high level of attention to detail regarding customer contracts, health scores, and stakeholder updates, ensuring no risk goes unnoticed.
On-the-Road Partnership: Travel to meet with customers and their brokers throughout the year to conduct business reviews, deepen relationships, and solidify HealthJoy’s position as a long-term strategic partner.