Senior Marketing Specialist

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.

Upside is growing fast across three lines of business — Medicaid, Medicare Advantage, and Employer — and we need a marketing operator who can move at the same pace. This is the first dedicated marketing hire supporting our sales and GTM team, which means you won't inherit a playbook.

You'll work directly with the VP of Marketing and a seasoned team of healthcare sales executives who have deep industry relationships and active pipelines. Your job is to help them move faster and close more deals with sharp collateral, smart campaigns, and content that gets Upside in front of the right people. The role is interdisciplinary by design: you'll touch content, events, client success, and operations depending on where the need is.

• Full-time, fully remote (must be based in the United States)
• Eastern time zone strongly preferred; Central is an option
• Schedule is Monday–Friday, with flexibility based on business needs and campaign cycles

• Build and maintain a sales collateral library — one-pagers, executive summaries, presentation decks — across Medicaid, Medicare Advantage, and Employer lines of business
• Partner directly with sales leaders to develop campaigns for specific clients, events, and trade shows
• Execute content strategy across owned channels — LinkedIn, blog, email — to expand Upside's reach as the leading housing resource in healthcare
• Draft and refine web copy, email marketing, and outreach sequences that support pipeline development
• Support account-based marketing (ABM) efforts, including prospect research and personalized campaign assets
• Manage and update the Upside website via WordPress, including landing pages, blog posts, and program pages
• Build and design presentation decks, one-pagers, and branded documents using Canva, PowerPoint, and Google Slides
• Use AI tools — including Claude, ChatGPT, Gamma, and Gemini — to accelerate content production and iterate quickly across campaigns
• Coordinate logistics and asset prep for conferences and trade shows, including pre-event materials and post-event follow-up
• Support client success and operations teams with marketing assets when needed
• Track campaign performance and surface insights to inform what's working and where to double down
• Complete additional duties as needed to support team and business outcomes as Upside scales

• 3+ years of marketing experience, with demonstrated ability to own work independently from brief to execution
• Proven track record creating sales enablement materials — one-pagers, decks, email copy — that help move deals forward
• Experience supporting a sales or GTM team in a fast-moving environment where priorities shift quickly
• Confident writer who can adapt tone by audience — formal and evidence-first for health plan buyers, business-first for employer buyers
• Hands-on proficiency with Canva, PowerPoint, and document design tools
• Comfortable building and publishing content in WordPress or a comparable CMS
• Strong organizational instincts — you track what's in-flight, follow through without reminders, and flag problems before they become fires
• High comfort with AI tools as part of your daily workflow, not just occasional use
• Accountability-first mindset — you take ownership of outcomes, not just tasks

• Experience in healthcare, health plans, or benefits — particularly Medicaid, Medicare Advantage, or employer benefits
• Background in or exposure to account-based marketing (ABM)
• Agency experience, especially supporting multiple clients or business lines simultaneously
• Familiarity with Salesforce or a comparable CRM
• Experience working across multiple lines of business or audience segments within a single marketing role