• Provide executive leadership for Funding and Dealer Support, ensuring alignment with organizational objectives and dealer experience standards. • Develop and execute strategic plans, including departmental KPIs, performance metrics, and incentive programs. • Lead, mentor, and develop managers and people leaders, fostering a culture of accountability, engagement, and professional growth. • Serve as a catalyst for modernization and continuous improvement, ensuring processes remain efficient, scalable, and aligned with industry best practices. • Ensure timely, accurate, and compliant processing of funding documents from receipt through loan purchase. • Establish and enforce policies and procedures to maintain operational consistency and regulatory compliance. • Drive process improvement initiatives and efficiency gains across departments and through cross-functional collaboration. • Lead dealer support operations, ensuring a centralized, one-stop support model and delivery of a white-glove dealer experience. • Assess and continuously improve dealer support practices, verification processes, and service metrics to enhance dealer satisfaction and operational performance. • Resolve complex or escalated funding and dealer-related issues, ensuring timely and effective outcomes while reinforcing strong dealer relationships.

Position Summary: The Regional Vice President (RVP) of Sales, reporting directly to the Vice President of Sales (East/West Region), is responsible for developing and executing regional territory strategies to drive the sale of Ameriflex products and services. This role involves strategic planning, forecasting, and managing all sales activities to expand sales revenue in an assigned territory. The RVP of Sales will oversee established customer relationships and proactively develop and manage a regional network of brokers while promoting Ameriflex's solutions. The RVP of Sales will play a critical role in driving the growth of Ameriflex by developing effective sales strategies, fostering strong client relationships, and leading the regional sales efforts. The ideal candidate will be a strategic thinker with a proven ability to execute sales plans and achieve revenue goals in a dynamic environment. Principal Duties & Responsibilities: - Strategic Planning & Territory Management: - Develop and execute a strategic sales plan for the assigned territory, including annual business plans with revenue and product goals. (Advanced) - Identify prospective client sources and develop growth strategies using a variety of communication methods, including direct contact, client seminars, and virtual or in-person presentations. (Advanced) - Stay current on industry trends, market conditions, and competitor activities to refine sales strategies. (Advanced) - Sales Leadership & Client Engagement: - Deliver customized presentations and position new services, marketing ideas, and concepts to assigned brokers, ensuring a tailored approach for different audience needs. (Advanced) - Build and maintain strong relationships with brokers and clients, proactively identifying opportunities to drive additional sales and strengthen partnerships. (Advanced) - Represent the company at national broker conferences, marketing meetings, and other industry events to enhance brand visibility and network with key stakeholders. (Advanced) - Performance Tracking & Reporting: - Meet or exceed annual sales objectives, continuously monitoring progress and adjusting strategies as needed. (Advanced) - Maintain accurate and up-to-date records of sales activities and account interactions using Salesforce, ensuring all data is captured for tracking and reporting purposes. (Advanced) - Participate in weekly sales meetings and regular CRO conference calls to review territory development, broker engagement, and the status of pending cases. (Intermediate) - Team Collaboration & Cross-Functional Support: - Collaborate with the CRO and other executive leaders to align territory strategies with the overall company sales plan and organizational objectives. (Advanced) - Coordinate with internal departments, including Marketing and Revenue Operations, to support sales initiatives and ensure resources are available to execute sales plans effectively. (Intermediate) - Provide input and feedback on product development, service enhancements, and marketing strategies based on market insights and client feedback. (Intermediate)

At UnitedHealthcare, we’re simplifying the health care experience, creating healthier communities and removing barriers to quality care. The work you do here impacts the lives of millions of people for the better. Come build the health care system of tomorrow, making it more responsive, affordable and optimized. Ready to make a difference? Join us to start Caring. Connecting. Growing together. The Vice President Sales, Labor & Trust position is accountable for achieving membership sales targets. This role is responsible for developing a strategic sales plan based on the assigned goals, which promotes a sustainable qualified sales pipeline leading to membership and revenue growth, and strategic consultant and stakeholder relationships. You’ll enjoy the flexibility to work remotely * from anywhere within the U.S. as you take on some tough challenges. Primary Responsibilities: - Achieve new business sales membership goals on an annual basis, focusing primarily on Labor & Trust Funds - Demonstrate strategic thinking and innovation based on knowledge of the market, competitors and solutions - Drive Labor & Trust/complex Sales and Business Planning and Membership Forecasting - Define sales processes that drive desired sales outcomes and identify improvements where and when needed - Demonstrate solid leadership qualities and organizational skills in directing the efforts of the sales or project team throughout the sales cycle - Manage consultant and customer expectations and contribute to a high level of customer satisfaction (NPS) - Understand and evaluate competitive activity and keep leadership and marketing apprised - Maintain a highly credible professional profile within the industry - Represent the organization in meetings, seminars, trade shows and networking events - Provide input to region and national teams for product enhancement & new product development - Communicate issues, concerns and problems in a solution-oriented manner - Provide management with timely reporting as required and requested - Successfully implement a direct prospecting strategy for Region and Markets - Work collaboratively with the client management team and national/regional resources to maximize results - Ensure accurate and timely entry of sales opportunity information using our sales tracking tools - Be a positive force and a team leader You’ll be rewarded and recognized for your performance in an environment that will challenge you and give you clear direction on what it takes to succeed in your role as well as provide development for other roles you may be interested in. Required Qualifications: - 7+ years of successful sales and/or sales management experience in Health Insurance - 7+ years of successful sales experience in large and complex sales negotiations - Consistent track record meeting/exceeding Sales Goals - ASO / Self-Funded Insurance Plans and Sales - Demonstrated success with Pipeline Opportunity Development and Management - Experience with CRM / Sales Tools and Methodology (i.e., SalesForce) - Experience with successful Negotiations skills and techniques - Extensive experience in advanced Health Insurance solutions sales with large Payer organizations - Knowledge of Taft-Hartley Multi-Employer Trust Funds; both Labor & Management Side - Successful consultative sales experience calling on Trustees, Fund Professionals, Consultants - Leadership in both hierarchical and team situations, within a highly matrixed organization - Clearly demonstrated strengths in persuasion, oral/written communications, analytical skills and sales production - History of building and maintaining solid positive business relationships at all decision levels - Driver’s License and access to a reliable transportation Preferred Qualifications: - Experience with Labor Sales Process - Experience working with Unions (particularly Labor Unions) - Experience working with Lobbyists and Governmental Affairs - Experience working in a highly matrixed organization Preferred Core Competencies: - Solid Drive for Results - Ability to Deal with Ambiguity - Versed at Conflict Management - Possess Organizational Agility and is Politically Savvy - Skilled at Managing and Communicating Vision and Purpose *All employees working remotely will be required to adhere to UnitedHealth Group’s Telecommuter Policy Pay is based on several factors including but not limited to local labor markets, education, work experience, certifications, etc. In addition to your salary, we offer benefits such as, a comprehensive benefits package, incentive and recognition programs, equity stock purchase and 401k contribution (all benefits are subject to eligibility requirements). No matter where or when you begin a career with us, you’ll find a far-reaching choice of benefits and incentives. The salary for this role will range from $75,000 to $160,000 annually based on full-time employment. We comply with all minimum wage laws as applicable. Application Deadline: This will be posted for a minimum of 2 business days or until a sufficient candidate pool has been collected. Job posting may come down early due to volume of applicants. At UnitedHealth Group, our mission is to help people live healthier lives and make the health system work better for everyone. We believe everyone–of every race, gender, sexuality, age, location and income–deserves the opportunity to live their healthiest life. Today, however, there are still far too many barriers to good health which are disproportionately experienced by people of color, historically marginalized groups and those with lower incomes. We are committed to mitigating our impact on the environment and enabling and delivering equitable care that addresses health disparities and improves health outcomes - an enterprise priority reflected in our mission. UnitedHealth Group is an Equal Employment Opportunity employer under applicable law and qualified applicants will receive consideration for employment without regard to race, national origin, religion, age, color, sex, sexual orientation, gender identity, disability, or protected veteran status, or any other characteristic protected by local, state, or federal laws, rules, or regulations. UnitedHealth Group is a drug - free workplace. Candidates are required to pass a drug test before beginning employment. #UHCPJ

About League Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart. Position Summary League is seeking a Director / AVP, Delivery Enablement, Operations & Excellence to build and lead a new function responsible for delivery infrastructure, governance, operational excellence, and organizational transformation across the entire Delivery organization. This is a senior leadership and transformation role. You will own the systems, standards, and capabilities that enable League’s delivery teams to operate with consistency, predictability, and quality at scale. Your mandate spans four interconnected pillars: Delivery Enablement (methodology, training, knowledge management, and tooling), Delivery Operations (capacity planning, utilization, metrics, quality assurance, and vendor/offshore excellence), Financial Performance (delivery P&L, margin analysis, and resource supply/demand modeling), and Excellence & Transformation (talent development, competency frameworks, Centers of Excellence, and strategic transformation programs). You will take League’s delivery organization from reliance on individual heroics to a systematic, scalable, and repeatable operating model. This requires building a dedicated team from scratch, defining the standard delivery playbook, and driving organization-wide adoption through deliberate change management. The role has a direct and measurable impact on League’s margin improvement trajectory from 15% to 25%. Reporting to the Chief Delivery Officer with a dotted line to the CTO for technical standards, you will sit on the Executive Delivery Council alongside the VP Program Management, SVP Solutions Engineering & Delivery, VP, Client Solutions and SVP Member & Employer Services. You will also lead the Delivery Operations Review and Talent & Development Council governance forums. In this role, you will: PILLAR 1: DELIVERY ENABLEMENT 1. Delivery Methodology & Standards - Define, implement, and continuously refine the Standard Delivery Playbook covering the end-to-end delivery lifecycle from discovery through deployment and post-implementation optimization. - Establish scalable intake, planning, estimation, and release governance processes. - Drive consistency in Agile practices, sprint hygiene, dependency management, and release readiness across all delivery teams. - Develop playbooks, templates, checklists, and documentation to enable repeatable execution across squads, client programs, and external partners. 2. Training, Onboarding & Certification - Own onboarding and continuous training programs for all delivery staff including engineers, project managers, product managers, designers, and QA testers. - Develop and deliver role-based training on product and business context, scoping and discovery, technical standards, project management methodology, and client communications. - Build a tiered certification program (Associate, Professional, Expert) to formalize competency development across the delivery organization. - Reduce time-to-productivity for new hires (target: 30 days to 60% productivity). - Extend enablement programs to SI partners and Developer Program customers to ensure consistent operational standards. 3. Tooling, Knowledge Management & AI - Own the standard Jira process: define the desired workflow, then configure the tool to match delivery needs. Drive 100% adoption. - Build and maintain a centralized platform knowledge repository organized by audience (engineer, PM, customer developer) with tiered content. - Own and maintain shared code libraries and design component libraries to promote reusability and consistency. - Drive adoption of AI tooling and workflows within the delivery organization; develop an AI-native delivery framework. 4. R&D Partnership & Release Enablement - Establish and manage a formal operating agreement with R&D covering platform documentation, dedicated SME access, and release readiness commitments. - Translate R&D documentation into delivery-focused training materials and maintain feedback loops on common implementation challenges. - Implement a Release Enablement gate in the R&D release process ensuring training materials, documentation, team briefings, and customer communications are ready before GA. PILLAR 2: DELIVERY OPERATIONS 5. Capacity Planning & Utilization Management - Own resource capacity planning and allocation across the delivery organization. - Manage utilization and billability targets (target: 75%+ sustainable utilization with quality maintained). - Identify systemic bottlenecks impacting velocity, throughput, or quality and implement structural improvements. - Drive resource supply/demand modeling to support pipeline forecasting and hiring decisions. 6. Quality Assurance & Delivery Governance - Establish clear delivery health indicators and stage-gate governance where appropriate. - Standardize release readiness criteria and go-live controls. - Conduct delivery audits to ensure process compliance and identify improvement opportunities. - Lead post-implementation retrospectives and systemic improvement loops. - Own offshore/nearshore operations excellence and vendor management for delivery partners. 7. Metrics, Reporting & Analytics - Define and maintain standardized reporting dashboards for leadership visibility into delivery health, risks, and trade-offs. - Develop executive-ready reporting for the CDO and senior leadership team, including Board-level materials. - Improve traceability from business requirements to engineering execution and drive automation of reporting. - Support strategic planning by surfacing trends across squads and initiatives. PILLAR 3: FINANCIAL PERFORMANCE 8. Delivery P&L & Margin Optimization - Own delivery P&L management and forecasting in partnership with Finance. - Conduct project margin analysis and drive optimization initiatives toward the 25% target. - Quantify expected impact of enablement initiatives on utilization efficiency, rework reduction, and delivery velocity. - Support commercial model development, pricing discipline, and cost management. PILLAR 4: EXCELLENCE & TRANSFORMATION 9. Talent Development & Organization Design - Develop delivery competency frameworks and career pathing for all delivery roles. - Partner with VPs and SVPs on hiring plans, performance management, and team capability building. - Lead the Talent & Development Council governance forum with all Delivery VPs. - Drive employee engagement and retention within the delivery organization. 10. Transformation Program Management - Own the strategic transformation program to move the delivery organization from current state to target operating model. - Establish and evolve Centers of Excellence for specialized domains. - Manage Board reporting and strategic communications related to delivery transformation progress. - Design and execute a change management strategy (ADKAR framework) to drive adoption of new processes and standards. - Build a coalition of champions across Engineering, PM, Design, and QA to evangelize new approaches. - Implement a graduated adoption approach—voluntary to strongly encouraged to mandatory—with documented exceptions. 11. Growth & Commercial Operations (Shared) - New customer implementation methodology development. - Onboarding playbooks and acceleration frameworks. - Commercial delivery strategy including packaging/pricing models and service catalog development. - Partner ecosystem development for delivery models. About you: - 10+ years in delivery operations, program management, or engineering operations within a SaaS or digital platform environment, with progressive leadership responsibility. - Proven track record building delivery organizations “from chaos to order”—demonstrated success standing up new functions, defining standard operating models, and driving large-scale process transformation and adoption. - P&L management experience: ownership of or significant contribution to delivery financial performance, margin analysis, and resource planning. - Proven experience working closely with Software Engineering teams and credibly engaging with technical audiences on architecture, SDLC, and tooling decisions. - Experience operating in complex, multi-client or multi-workstream environments with both onshore and offshore delivery teams. - Enablement and training experience: ability to build and deliver scalable training materials, onboarding programs, and certification curricula. - Organizational change management expertise with demonstrated success driving adoption across cross-functional teams at scale. - Experience building and managing high-performing teams as well as coordinating matrixed resources across multiple functions. - Prior experience in digital health, health tech, or highly regulated environments is a strong asset. Security-Related Responsibilities: - Ensure access management is performed in compliance with the employee's role and responsibilities - Responsibility and accountability for executing League's policies and procedures within the department/ team - Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations - Compliance with Information Security Policies US APPLICANTS ONLY: The US-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all US locations. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process. Compensation range for USA applicants only $212,200—$259,400 USD Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. If you are an individual in need of assistance at any time during our recruitment process, please contact us at recruitinginfo@league.com. Our Application Process: Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps - You should receive a confirmation email after submitting your application. - A recruiter (not a computer) reviews all applications at League. - If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring. - The final step is an offer, which we hope you will accept! - Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring. Here are some additional resources to learn more about League: - Learn about our platform, leadership team and partners - Highmark Health, Google Cloud, League: new digital front door to seamless care - Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors - League raises $95 million USD in Series C to build world’s leading healthcare CX platform - Forbes x League: The Platformization Of Healthcare Is Here - Fast Company x League: If we want better innovations in healthtech, we need more competition Work Location: We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. Regardless of the role’s posted location, all Toronto-area Leaguers (living within 65 km of our downtown HQ) collaborate in-office Monday through Thursday. Depending on your distance to the office, you’ll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep-work time. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location. Recognize and Avoid Employment scams. Practice safe job searching. Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here. Use of AI Notice We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here. Privacy Policy Review our Privacy Policy for information on how League is protecting personal data.