Vice President of Medicare Sales
4 days ago
Chicago
Introduction At Gallagher Benefit Services, you’re a trusted partner to organizations navigating some of their most important people decisions. We help clients build better workplaces, where people feel supported, empowered, and inspired to thrive. Whether it’s shaping benefit strategies, designing wellbeing programs, or advising on workforce challenges, the work you do here creates meaningful change for businesses and the people who power them. We’re a community of bold explorers, trusted experts, and compassionate partners; working side by side to solve problems, and shape the future of work. Here, curiosity is encouraged, collaboration is second nature, and your ideas have room to grow. If you’re looking for a place where your contribution matters and where you can help build a better world of work; think of Gallagher. Overview Your Way Insurance is a people-first organization built on compassion, integrity, and service. Our greatest strength lies in our talented and driven team, dedicated to helping seniors find Medicare plans that truly fit their needs, the right way. Through our one-stop shopping experience, we make it easy to compare top national health insurance carriers and choose coverage with confidence. Now part of Gallagher, a global leader in insurance, risk management, and consulting, you’ll join a network of professionals committed to empowering individuals, businesses, and communities to thrive. Whether you're supporting clients directly or contributing behind the scenes, you'll be part of a culture defined Your Way: shared values, excellence, and a passion for doing what's right. We believe every candidate brings something unique to the table, including you! This is a fully remote role. An application with us takes only 3 minutes! How you'll make an impact • Own overall sales performance and business outcomes across a 300–400-person sales organization, including revenue, conversion, effectuation, CAC, and profitability, with direct accountability for results., • Lead, coach, and develop 4–6 Sales Directors, ensuring strong leadership coverage, clear ownership, and consistent execution across all teams and regions., • Set and drive the sales strategy and operating plan, translating company goals into clear initiatives, targets, and execution rhythms across a large, complex organization., • Own and drive major sales initiatives end‑to‑end, including growth programs, productivity improvements, organizational changes, and culture‑shaping initiatives that reinforce accountability, performance, and leadership expectations—without reliance on escalation., • Establish and enforce performance management rigor across the organization, including KPI inspection, forecasting, leadership reviews, and corrective action through Directors., • Partner closely with Strategy, Training, WFM, Finance, Compliance, Recruiting, and HR to align strategy, remove friction, and ensure initiatives and cultural expectations scale effectively at every employee level., • Build, reinforce, and protect a strong sales culture focused on ownership, accountability, development, and continuous improvement, holding leaders responsible for both results and how results are achieved., • Act as the senior decision-maker for sales execution, solving complex, cross‑team problems and making clear tradeoffs in fast‑moving and ambiguous environments., • Active Resident Health Insurance License, • Proven experience in a leadership role leading leaders of teams, preferably within the Medicare or insurance industry., • In-depth knowledge of Medicare regulations, plan options, and sales processes., • Strong coaching and mentoring skills with the ability to motivate and develop a high-performing team of leaders., • Excellent communication and interpersonal skills to build effective relationships with team members and stakeholders., • Results-oriented mindset with a track record of achieving sales targets and driving team success. We offer a competitive and comprehensive compensation package. The base salary range represents the anticipated low end and high end of the range for this position. The actual compensation will be influenced by a wide range of factors including, but not limited to previous experience, education, pay market/geography, complexity or scope, specialized skill set, lines of business/practice area, supply/demand, and scheduled hours. On top of a competitive salary, great teams and exciting career opportunities, we also offer a wide range of benefits. Below are the minimum core benefits you’ll get, depending on your job level these benefits may improve: • Medical/dental/vision plans, which start from day one!, • Life and accident insurance, • 401(K) and Roth options, • Tax-advantaged accounts (HSA, FSA), • Educational expense reimbursement, • Digital mental health services (Talkspace), • Flexible work hours (availability varies by office and job function), • Training programs, • Gallagher Thrive program – elevating your health through challenges, workshops and digital fitness programs for your overall wellbeing, • Charitable matching gift program We value inclusion and diversity Click Here to review our U.S. Eligibility Requirements Inclusion and diversity (I&D) is a core part of our business, and it’s embedded into the fabric of our organization. For more than 95 years, Gallagher has led with a commitment to sustainability and to support the communities where we live and work. Gallagher embraces our employees’ diverse identities, experiences and talents, allowing us to better serve our clients and communities. We see inclusion as a conscious commitment and diversity as a vital strength. By embracing diversity in all its forms, we live out The Gallagher Way to its fullest. Gallagher believes that all persons are entitled to equal employment opportunity and prohibits any form of discrimination by its managers, employees, vendors or customers based on race, color, religion, creed, gender (including pregnancy status), sexual orientation, gender identity (which includes transgender and other gender non-conforming individuals), gender expression, hair expression, marital status, parental status, age, national origin, ancestry, disability, medical condition, genetic information, veteran or military status, citizenship status, or any other characteristic protected (herein referred to as “protected characteristics”) by applicable federal, state, or local laws. Equal employment opportunity will be extended in all aspects of the employer-employee relationship, including, but not limited to, recruitment, hiring, training, promotion, transfer, demotion, compensation, benefits, layoff, and termination. In addition, Gallagher will make reasonable accommodations to known physical or mental limitations of an otherwise qualified person with a disability, unless the accommodation would impose an undue hardship on the operation of our business.