Fort Lauderdale, Florida, United States · Remote Solely
$175k–$200k/yr
About Upside: Upside is a housing-focused care partner helping people experiencing housing instability take the next step toward stability. We partner with health plans and care organizations to identify members at risk,…
Skills: Payer Sales, Enterprise Sales, Business Development, Medicaid MCO Partnerships, Medicare Advantage
Doral, Florida, United States · On-site
$15/hr–$19/hr
Be part of an amazing story Macy’s is more than just a store. We’re a story. One that’s captured the hearts and minds of America for more than 160 years. A story about innovations and traditions…about inspiring stores an…
Skills: Customer Engagement, Sales Techniques, Hospitality, Product Knowledge, Cash Handling
Gainesville, Florida, United States · Hybrid
$60k–$90k/yr
Benefits: Work close to home No cold calling Health and Retirement Benefits Pre-set appointments (new and repeat clients) Ongoing mentorship 1 week paid sales training Hybrid- Remote Position Direct track for Senior Sale…
Skills: Sales, Design, Communication, Customer Relationship Management, Problem Solving
Fort Myers, Florida, United States · On-site
What You Need To Know Shape a remarkable future with us. Build a career working for an industry leader that truly invests in their people – and equips them with leading technology, continuous learning, and the ability to…
Skills: Merchandising, Display Construction, Inventory Stocking, Relationship Management, Point-of-Sale Installation
East Lake-Orient Park, Florida, United States · On-site
Requisition Number: 229416 Job Description Cintas is offering an exciting Management Trainee program designed to kickstart your professional career. We are seeking a motivated and dynamic Management Trainee to join this …
Skills: Leadership, Outside Sales, Production Management, Warehouse Management, Office Management
Palm Bay, Florida, United States · On-site
$175k–$325k/yr
Job Title: Director, Business Development Job Code: 40351 Job Location: Washington DC. or Palm Bay FL. Schedule: 9/80- Employees work 9 out of every 14 days – totaling 80 hours worked, and have every other Friday off Job…
Skills: Business Development, Strategic Planning, Maritime Domain Expertise, International Sales, Relationship Management
Marco Island, Florida, United States · On-site
Job Summary The Cannabis Advisor is responsible for providing exceptional individualized customer service, educational consulting, and in some cases patient record management. Essential Duties and Responsibilities Posses…
Skills: Customer Service, Cannabis Education, Patient Record Management, POS Systems, Inventory Management
Bal Harbour, Florida, United States · On-site
Description We are looking for a dynamic and inspirational Store/Retail/Counter Manager to lead, coach and develop our team of Sales Associates to achieve all sales, customer service and operational targets. Candidates s…
Skills: Retail Management, Leadership, Coaching, Business Planning, Customer Relationship Management
Orlando, Florida, United States · On-site
Location: FL-Orlando-John Young Job Title: Media Consultant/Account Executive - Orlando Radio Position Overview Do you have a drive to win in a Sales environment? Do you have a passion for helping local businesses grow t…
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Hillsborough County, Florida, United States · On-site
Job Details Division: Trademark Metals Recycling LLC Location: Tampa, FL, United States Compensation: Average annual earnings: $67,000 (includes hourly base pay, weekly overtime opportunities, and bonuses) About Nucor We…
Skills: Inside Sales, Cold Calling, Customer Relationship Management, Pricing Quotation, Lead Generation
Bridgeport, Connecticut, United States · Remote OK
$115k–$165k/yr
Shape the Future with Us. At Lubrizol, we’re transforming the specialty chemicals industry through science, sustainability, and a culture of inclusion. As part of our global team, you’ll be empowered to make a real impac…
Skills: Product Management, Market Analysis, Go-To-Market Strategy, Business Development, Innovation Roadmap Development
Florida, United States · Remote Solely
Check us out here! https://careers.fisheragencies.com/?invite=cassidygriffin We are a growing organization dedicated to helping working families access valuable supplemental benefits and financial protection solutions. T…
Skills: Communication, Interpersonal Skills, Customer Service, Virtual Meeting Platforms, Leadership
Miami-Dade County, Florida, United States · On-site
$66k–$75k/yr
As the largest jewelery brand in the world, we a give a voice to millions of people’s loves every day. Our beautiful products empower people all around the world to express themselves. We are proud to be part of their st…
Skills: Store Management, Sales Leadership, KPI Management, Coaching, Recruiting
Miami, Florida, United States · On-site
$66k–$80k/yr
As the largest jewelery brand in the world, we a give a voice to millions of people’s loves every day. Our beautiful products empower people all around the world to express themselves. We are proud to be part of their st…
Skills: Store Management, Sales Leadership, KPI Management, Coaching, Recruiting
Aventura, Florida, United States · On-site
At a Glance As a Lead Store Advisor, you will leverage your leadership skills to drive sales performance, mentor Store Advisors, and maintain operational excellence. Your responsibilities will include supervising custome…
Skills: Team Leadership, Retail Operations, Inventory Management, Visual Merchandising, Customer Relationship Management
Aventura, Florida, United States · On-site
In Short As a Store Advisor, you will be a key player in driving a premium, individualized fan experience in-store. Your focus will be to master the fundamentals of our Cloud CX philosophy to deliver "wow" moments and en…
Skills: Customer Service, Retail Operations, Inventory Management, Communication Skills, Organizational Skills
Florida, United States · On-site
$175k–$298k/yr
Join the Future of Security at Netskope Netskope (NASDAQ: NTSK) is a leader in modern security and networking for the cloud and AI era. We secure and accelerate cloud, data, and AI in real time, everywhere. Thousands of …
Skills: Consultative Sales, Account Strategy, Channel Partner Management, Cybersecurity Sales, Enterprise Software Sales
Viera, Florida, United States · On-site
$30k–$200k/yr
Named America's #1 Premium Furniture Retailer by Newsweek, Ethan Allen is a leading interior design destination combining state-of-the-art technology with personal service. After more than 90 profitable years in business…
Skills: Interior design, Sales, Space planning, Fabric coordination, Product selection
Tampa, Florida, United States · Remote Solely
$80k–$115k/yr
Paradigm is an accountable specialty care management organization focused on improving the lives of people with complex injuries and diagnoses. The company has been a pioneer in value-based care since 1991 and has an exc…
Skills: Provider Marketing, Account Management, Sales, Workers Compensation, Healthcare
GIA Legacy PlanningClearwater, Florida, United States · Remote Solely
Location: Remote Position/ Work from Home Job Type: Full-Time/Part-Time Compensation: 100% Uncapped Commission-Based About Us: GIA Legacy Planning is a dynamic, client-focused insurance agency specializing in personalize…
Skills: Insurance sales, Lead generation, Client relationship management, Time management, Communication skills
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Lead growth and execute sales strategies for Medicaid MCOs and Medicare Advantage opportunities to drive housing stability partnerships. Manage the full sales cycle from prospecting and RFP responses to contract execution and implementation handoff.
Requires 10-15+ years of healthcare enterprise sales experience with a proven track record of closing large-scale payer contracts. Deep knowledge of Medicaid/Medicare managed care, SDOH, and value-based contracting models is essential.
About Upside:
Upside is a housing-focused care partner helping people experiencing housing instability take the next step toward stability. We partner with health plans and care organizations to identify members at risk, build a clear housing plan, and drive the work forward through placement and stabilization.
Upside owns the entire housing process from start to finish. Our team engages members, coordinates with local providers and community resources, manages logistics and documentation, and stays involved until the issue is resolved. Our approach is human-first and outcome-driven, measured by real results like stable housing, completed moves, safer living environments, and successful transitions.
About the Opportunity:
Upside is hiring a VP Sales, Health Plans to lead growth across Medicaid MCOs and emerging Medicare Advantage opportunities. This is a senior sales leadership role focused on building and closing large-scale partnerships with health plans that are looking for solutions around housing stability, SDOH, value-based care, member outcomes, and total cost of care.
This role reports to the EVP of Sales and GTM and will own a high-priority payer segment, including flagship account strategy, executive relationships, RFPs, pipeline development, pricing strategy, and contract execution. You’ll work closely with Marketing, BDR, Finance, Product, Clinical, and Client Success to move complex payer opportunities from first conversation through implementation handoff.
Work Location and Schedule:
Full-time, fully remote (must be based in the United States)
Coverage aligned to Eastern or Central time
Monday–Friday schedule, with travel as needed for payer meetings, state meetings, RFP-related meetings, and industry conferences
What You’ll Do:
Own and execute the sales strategy for Medicaid MCOs and emerging Medicare Advantage opportunities
Build and manage a qualified pipeline of high-value payer opportunities, with accountability for revenue targets
Lead flagship health plan opportunities from account mapping and outreach through proposal, negotiation, contracting, and close
Identify and convert high-priority payer opportunities across Medicaid managed care, Medicare Advantage, and adjacent government-funded healthcare programs
Build relationships with senior payer leaders across population health, clinical, quality, operations, finance, strategy, and executive leadership
Serve as a credible face of Upside in senior conversations with health plan executives, state stakeholders, industry groups, and market partners
Lead the strategy and execution of major payer RFP responses, ensuring Upside’s clinical, operational, and financial value proposition is clearly positioned
Tailor Upside’s housing stability and SDOH value proposition to each payer’s priorities, including quality, cost of care, member engagement, compliance, and outcomes
Partner with Finance and Product to structure pricing and deal models, including PMPM, shared savings, performance-based, or other payer-aligned arrangements
Work with Product and Clinical teams to ensure payer feedback, compliance needs, reporting requirements, and market expectations are reflected in future roadmap discussions
Provide competitive intelligence and market feedback to strengthen Upside’s positioning in housing, SDOH, value-based care, and payer partnerships
Build and maintain relationships with state health agencies, managed care associations, payer forums, and industry groups
Maintain strong CRM discipline, including pipeline updates, forecasting, next steps, deal risks, and executive-level reporting
Coordinate cross-functionally to ensure proposals include the latest outcomes data, ROI story, operational model, and implementation assumptions
Partner with Client Success and Implementation to ensure closed partnerships are handed off clearly and commercial commitments are operationalized well
Support broader GTM strategy, market expansion, and team growth as Upside scales its payer partnerships function
What We’re Looking For:
10–15+ years of payer sales, healthcare enterprise sales, business development, or payer partnerships experience
7+ years of experience selling to or partnering with Medicaid MCOs, Medicare Advantage plans, health plans, or government payer organizations
Proven track record personally closing large-scale payer contracts and managing high-value revenue targets
Experience owning a full sales cycle independently, from account mapping and prospecting through negotiation, contracting, and close
Deep understanding of Medicaid managed care, Medicare Advantage, payer priorities, government-funded healthcare programs, and health plan buying cycles
Experience navigating complex RFPs, procurement processes, legal review, compliance review, executive approvals, and multi-stakeholder decision-making
Strong understanding of SDOH, housing stability, value-based care, population health, quality improvement, member engagement, and total cost of care
Experience selling or positioning solutions related to housing, care management, care coordination, behavioral health, social care, complex populations, or adjacent healthcare services
Ability to engage credibly with C-suite and senior payer stakeholders, including clinical, finance, operations, quality, strategy, and population health leaders
Familiarity with PMPM, shared savings, value-based, performance-based, or other payer contracting models
Experience partnering with Product and Finance to shape pricing, deal structure, reporting expectations, and payer-specific contract terms
Strong written and verbal communication skills, including executive presentations, proposals, RFP responses, and internal deal strategy materials
Strong pipeline management and forecasting discipline, especially in long-cycle enterprise sales environments
Existing relationships with Medicaid MCOs, Medicare Advantage plans, state health agencies, managed care associations, or payer executives preferred
Experience with ACAP, MHPA, state Medicaid agencies, or managed care industry groups is a plus
Bachelor’s degree preferred; MBA, MPH, MHA, or related advanced degree is a plus
Ability to travel as needed for payer meetings, conferences, state meetings, and market development
Compensation and Benefits:
Base salary range: $175,000–$200,000
On-target earnings: $350,000–$400,000
Stock options
Medical, dental, and vision coverage
Paid time off and company holidays
Transforming Health Through Housing, Delivering Stability, Improved Outcomes, and Savings for Health Plans Nationwide.
Upside is a housing-focused care partner helping people experiencing housing instability take the next step toward stability. We partner with health plans and care organizations to identify members at risk, build a clear housing plan, and drive the work forward through placement and stabilization. Upside owns the entire housing process from start to finish. Our team engages members, coordinates with local providers and community resources, manages logistics and documentation, and stays involved until the issue is resolved. Our approach is human-first and outcome-driven, measured by real results like stable housing, completed moves, safer living environments, and successful transitions.
Offices: 200 E Las Olas Blvd 14th Floor, Fort Lauderdale, Florida 33301, US
View all jobs at UpsideBased on 3608 listings with disclosed salaries, most sales jobs in Florida pay between $54k–$150k per year. Individual offers vary with seniority, company size, and specialization.
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