7 Health Insurance Startups to Watch in 2025

The health insurance landscape, long dominated by legacy giants, is undergoing a seismic shift. A new wave of technology-driven health insurance startups is rewriting the rules, focusing on user experience, transparency, and data-driven personalization. These innovators are tackling deeply entrenched problems, from simplifying the convoluted process of enrolling in an ACA plan to providing more responsive and tailored coverage for small businesses and Medicare recipients. For example, the average consumer has to navigate complex jargon and opaque pricing, leading to a Net Promoter Score (NPS) for the health insurance industry that often lags far behind other sectors. These startups are building a more accessible and efficient system from the ground up to fix that.

This article provides a strategic deep dive into the key players making waves. For each company, we analyze critical business intelligence to give you a competitive edge. You will find a comprehensive breakdown of:

• Funding & Valuation: The latest investment rounds and financial standing. For instance, Oscar Health raised over $1.6 billion before its IPO, signaling massive investor confidence.
• Growth Signals: Actionable data on hiring trends, website traffic, and ad spend. A practical insight is that a spike in hiring for "sales development representatives" often precedes a new market launch.
• Core Product: A clear look at their primary use case and target market.
• Tech Stack: Indicators of the technologies powering their platforms.
• Outreach Triggers: Specific insights for agencies, recruiters, and investors.

The new guard of health insurance heavily relies on advanced IT services driving healthcare transformation to modernize outdated systems and deliver better care. This listicle is your roadmap to understanding who is leading this charge. We provide the essential data, direct links, and tactical insights you need to identify opportunities, understand the competitive landscape, and engage with the startups defining the future of healthcare coverage.

1. Oscar Health: The Tech-Forward Challenger

Oscar Health has firmly positioned itself as one of the most recognizable tech-first players in the individual insurance market. Unlike legacy insurers burdened by outdated systems, Oscar built its platform from the ground up with a singular focus on the member experience. This approach directly challenges the traditionally opaque and complex nature of health insurance by delivering a consumer-grade digital interface. The core of their service is an app-centric model that empowers members to manage their health journey seamlessly. As of early 2024, the company serves approximately 1 million members, demonstrating significant market penetration.

This digital-first strategy makes Oscar a standout among health insurance startups, appealing to a generation of consumers who expect on-demand services and intuitive design. The company primarily offers ACA-compliant individual and family plans, directly integrating with the Health Insurance Marketplace for enrollment. Availability, however, is a key consideration; Oscar operates in specific counties across approximately 18 states, meaning potential members must verify coverage in their exact geographic location.

Product, User Experience, and Market Position

Oscar's platform shines in its usability. Members are assigned a dedicated 'Care Team' accessible via secure messaging, providing a consistent point of contact for questions about benefits, claims, or finding care. This concierge-style service is a significant differentiator from the call-center lottery common with traditional carriers, where a member might speak to a different agent every time they call.

Key features that define the Oscar experience include:

• Integrated Virtual Care: The app provides easy access to virtual primary care and urgent care, often with $0 co-pays. For example, a member can book a same-day virtual appointment with a doctor for a minor illness directly through the app, avoiding a trip to an urgent care clinic.
• Transparent Prescription Tools: Members can search for prescriptions, view costs at different pharmacies, and manage refills directly within the app, demystifying drug pricing.
• Step Tracking Rewards: In many plans, Oscar integrates with fitness trackers like Google Fit and Apple Health, rewarding members with up to $100 in Amazon gift cards per year for meeting daily step goals.

Outreach Triggers and Strategic Insights

Oscar's aggressive growth, significant venture backing, and status as a publicly traded company (NYSE: OSCR) create multiple entry points for strategic partners. Their continuous investment in technology and member acquisition presents clear opportunities. For more details on their financial journey, which includes over $1.6 billion in funding before their 2021 IPO, you can explore the history of Oscar Health's funding rounds.

For Agencies & Investors:

• Marketing & Ad Spend: Oscar maintains a high-visibility marketing presence during the annual Open Enrollment period (Nov 1 – Jan 15). Performance marketing and creative agencies could find opportunities by analyzing their campaign performance and offering strategies to boost conversion rates in competitive markets like Florida and Texas.
• Tech & Automation: As Oscar scales, the need for sophisticated automation in member support, claims processing, and data analytics grows. For example, a tech consultancy could propose an AI-powered chatbot to handle common member inquiries, freeing up the human Care Team for more complex issues.
• Recruitment: The company is consistently hiring for roles in engineering, product management, data science, and marketing, reflecting its focus on technological innovation. Recruiters specializing in tech and healthcare talent have a prime target here.

2. HealthSherpa: The ACA Enrollment Engine

HealthSherpa has carved out a critical niche not as an insurance carrier, but as the leading technology platform for enrolling in Affordable Care Act (ACA) plans. It operates as a federally-approved Enhanced Direct Enrollment (EDE) partner, which means it offers a faster, more intuitive interface for the exact same plans, subsidies, and prices found on HealthCare.gov. To date, HealthSherpa has helped over 12 million people enroll in coverage. This focus on simplifying the often-baffling enrollment process has made it an indispensable tool for consumers and, most notably, for insurance agents and brokers.

By streamlining the application and comparison workflow, HealthSherpa directly addresses the friction points of the public marketplace. The platform is completely free for consumers and is available in all states served by the federal HealthCare.gov marketplace. This singular focus on enrollment technology makes it a unique and powerful player among health insurance startups, acting as a critical middleware layer between consumers, agents, and government infrastructure. Its primary value is not in creating new insurance products, but in making existing ones dramatically more accessible.

Product, User Experience, and Market Position

HealthSherpa’s platform is designed for speed and clarity. Where the official government portal can be cumbersome, HealthSherpa presents a clean, guided flow that allows users to compare plans, check for their specific doctors and prescriptions, and complete an entire application in an average of 15 minutes or less. Its business model heavily relies on its agent-facing platform, which provides brokers with a sophisticated toolkit to manage their entire book of business, from client applications to post-enrollment support like document uploads and binder payments.

Key features that define the HealthSherpa experience include:

• Enhanced Direct Enrollment (EDE): This full integration with HealthCare.gov allows for a complete end-to-end enrollment process without ever leaving the HealthSherpa site, a significant UX improvement.
• Integrated Provider & Rx Search: Before committing to a plan, users can search for their specific doctors, hospitals, and prescription drugs to see which plans cover them, preventing post-enrollment surprises. A practical example is a user searching for their oncologist to ensure they remain in-network.
• Broker-Centric Tools: The platform offers a free, powerful CRM for agents to track applications, manage client communication, and streamline their Open Enrollment workflow, cementing its B2B market leadership.

Outreach Triggers and Strategic Insights

HealthSherpa's position as the dominant ACA enrollment platform for the agent channel presents clear opportunities for B2B-focused partners. The company's growth is directly tied to the performance of the ACA marketplace and its ability to equip agents with the best technology. Its acquisition by GoodRx in 2021 for $150 million underscores its value and integration into the broader digital health ecosystem.

For Agencies & Investors:

• Agent & Broker Marketing: As HealthSherpa’s primary user base is insurance agents, marketing agencies specializing in B2B lead generation and professional services could find significant opportunities. A practical example would be running a LinkedIn ad campaign targeting users with "Insurance Broker" in their job title.
• API & Tech Integration: Companies offering complementary services, such as E&O insurance for agents, advanced CRM features, or commission tracking software, could explore partnership and API integration opportunities to tap into HealthSherpa's vast agent network of over 60,000 brokers.
• Recruitment: HealthSherpa consistently seeks talent in software engineering (particularly Ruby on Rails), partner success, and B2B marketing. Recruiters with experience in SaaS and insurtech can find a strong target for placing specialized roles.

3. Stride Health: The Benefits Platform for the Gig Economy

Stride Health has carved out a distinct and critical niche within the health insurance landscape by focusing exclusively on the needs of independent workers. This includes freelancers, gig economy participants, and 1099 contractors who lack traditional employer-sponsored benefits. Stride operates not as a carrier, but as an enhanced enrollment partner for the Affordable Care Act (ACA) marketplace, simplifying the process of finding and enrolling in individual health plans. Its platform aggregates on-exchange plans, ensuring users see the same options and pricing as they would on HealthCare.gov. It has helped over 3 million workers save a collective $4 billion on their taxes and insurance.

The company’s unique value proposition is its ecosystem of tools built around the core insurance offering, all tailored to the self-employed professional. This specialized focus makes Stride a go-to resource and a vital partner for companies like Uber, DoorDash, and Amazon Flex, who offer it as a benefits solution to their vast networks of independent contractors. By addressing the specific financial and administrative pain points of this workforce, Stride has cemented its position as one of the most practical health insurance startups for the modern economy.

Product, User Experience, and Market Position

Stride’s user experience is designed for simplicity and speed, guiding users through the complex process of estimating income—a major challenge for gig workers—and qualifying for subsidies. The platform provides personalized plan recommendations based on an individual's specific health needs, preferred doctors, and prescription drug requirements. A human support team is available to provide guidance, a crucial feature for those navigating the insurance market for the first time.

Key features that define the Stride experience include:

• Integrated Financial Tools: Beyond insurance, Stride offers a free app to help users track mileage and business expenses, simplifying tax preparation and maximizing deductions. For example, a rideshare driver can automatically log their miles to claim a significant tax write-off at the end of the year.
• Official Marketplace Integration: As a recognized partner of HealthCare.gov, Stride offers the same plans, subsidies, and consumer protections, but with a more user-friendly interface. In some states, users are seamlessly redirected to their state’s exchange to finalize enrollment.
• Powerful Partner Ecosystem: Stride’s primary go-to-market strategy involves co-branded partnerships with major gig economy platforms, providing it with direct access to millions of potential users.

Outreach Triggers and Strategic Insights

Stride's deep integration with the gig economy and its status as a venture-backed entity (having raised over $96 million) create numerous opportunities for collaboration. The company’s B2B2C model means it is constantly seeking to add value for both its enterprise partners and end-users. You can discover more about Stride Health's profile and its market traction.

For Agencies & Investors:

• Partnership & Business Development: Companies providing services to independent workers (e.g., financial planning, accounting software, legal services) could explore co-marketing or integration partnerships. For instance, a neobank could partner with Stride to offer its users a business checking account.
• Content & SEO: Stride's business relies on being a trusted educational resource. Content agencies specializing in finance, tax law, and healthcare can propose strategies to create guides and tools—like an "Ultimate Guide to 1099 Taxes"—that attract and engage independent professionals.
• Recruitment: As Stride expands its product offerings and partner network, it frequently hires for roles in business development, partner management, engineering, and member experience. Recruiters with expertise in these areas will find consistent opportunities.

4. Oscar Health: The Tech-Forward Challenger

Oscar Health has firmly positioned itself as one of the most recognizable tech-first players in the individual insurance market. Unlike legacy insurers burdened by outdated systems, Oscar built its platform from the ground up with a singular focus on the member experience. This approach directly challenges the traditionally opaque and complex nature of health insurance by delivering a consumer-grade digital interface. The core of their service is an app-centric model that empowers members to manage their health journey seamlessly.

This digital-first strategy makes Oscar a standout among health insurance startups, appealing to a generation of consumers who expect on-demand services and intuitive design. The company primarily offers ACA-compliant individual and family plans, directly integrating with the Health Insurance Marketplace for enrollment. Availability, however, is a key consideration; Oscar operates in specific counties across approximately 18 states, meaning potential members must verify coverage in their exact geographic location.

Product, User Experience, and Market Position

Oscar's platform shines in its usability. Members are assigned a dedicated 'Care Team' accessible via secure messaging, providing a consistent point of contact for questions about benefits, claims, or finding care. This concierge-style service is a significant differentiator from the call-center lottery common with traditional carriers.

Key features that define the Oscar experience include:

• Integrated Virtual Care: The app provides easy access to virtual primary care and urgent care, often with low or no co-pays, encouraging proactive and convenient health management.
• Transparent Prescription Tools: Members can search for prescriptions, view costs at different pharmacies, and manage refills directly within the app, demystifying drug pricing.
• Step Tracking Rewards: In many plans, Oscar integrates with fitness trackers like Google Fit and Apple Health, rewarding members with Amazon gift cards for meeting daily step goals.

Outreach Triggers and Strategic Insights

Oscar's aggressive growth, significant venture backing, and status as a publicly traded company (NYSE: OSCR) create multiple entry points for strategic partners. Their continuous investment in technology and member acquisition presents clear opportunities. For more details on their financial journey, you can explore the history of Oscar Health's funding rounds.

For Agencies & Investors:

• Marketing & Ad Spend: Oscar maintains a high-visibility marketing presence during the annual Open Enrollment period. Performance marketing and creative agencies could find opportunities by analyzing their campaign performance and offering strategies to boost conversion rates in competitive markets.
• Tech & Automation: As Oscar scales, the need for sophisticated automation in member support, claims processing, and data analytics grows. Tech consultants specializing in AI-driven customer service or data infrastructure could provide significant value.
• Recruitment: The company is consistently hiring for roles in engineering, product management, data science, and marketing, reflecting its focus on technological innovation. Recruiters specializing in tech and healthcare talent have a prime target here.

5. Devoted Health: The High-Touch Medicare Advantage Innovator

Devoted Health is a fast-growing player focused exclusively on the Medicare Advantage (MA) market, a segment ripe for disruption with over 30 million enrollees nationwide. Founded by veterans of Athenahealth, the company combines technology with a high-touch, concierge-style service model to support seniors. Instead of a broad insurance play, Devoted has zeroed in on providing a more integrated and supportive experience for Medicare beneficiaries, aiming to deliver healthcare that feels like it’s being managed by family.

This focused strategy makes Devoted Health one of the most compelling health insurance startups in the senior care space. They offer a range of Medicare Advantage HMO and PPO plans, many with $0 monthly premiums and robust supplemental benefits. As with all MA plans, availability is highly localized; Devoted operates in specific counties across states like Florida, Texas, Arizona, and Ohio, requiring prospective members to verify eligibility by ZIP code directly on their website.

Product, User Experience, and Market Position

Devoted Health’s core differentiator is its "Devoted Guide" program. Each member is connected with a dedicated guide who acts as a single point of contact for all their healthcare needs, from answering benefit questions and scheduling appointments to coordinating care with doctors. This personal touch is designed to simplify the often-confusing world of Medicare for its members.

Key features that define the Devoted Health experience include:

• Concierge-Style Member Support: The U.S.-based Devoted Guides provide personalized, proactive support. A practical example is a guide proactively calling a member to remind them to schedule their annual wellness visit.
• Rich Supplemental Benefits: Many Devoted plans include valuable extras not covered by Original Medicare, such as dental and vision coverage, hearing aid allowances, and quarterly stipends of up to $150 for over-the-counter (OTC) products.
• Seamless Online Enrollment: The website features a straightforward ZIP code lookup and a clean, guided online enrollment flow, making it easy for seniors or their caregivers to compare plans and sign up.

Outreach Triggers and Strategic Insights

Devoted Health’s significant venture capital backing and rapid expansion into new geographic markets signal a company in an aggressive growth phase. Their success has attracted over $2 billion in funding, highlighting strong investor confidence. For a deeper look into the financial trends powering companies like Devoted, you can explore venture capital investment trends in health-tech.

For Agencies & Investors:

• Targeted Senior Marketing: Devoted's marketing is heavily concentrated around the Medicare Annual Enrollment Period (AEP), from October 15 to December 7. Agencies specializing in direct mail, local media, and digital marketing for the 65+ demographic could offer hyper-targeted campaigns to boost member acquisition in specific counties.
• Member Engagement Tech: As they scale, Devoted needs technology to maintain its high-touch service model. Companies offering solutions for personalized member communication, remote patient monitoring, or telehealth platforms tailored for seniors could find a receptive partner.
• Talent Acquisition: Devoted is frequently hiring for clinical roles, member service (Devoted Guides), and technology positions to support its growth. Recruiters with expertise in healthcare operations and patient-facing roles have a clear opportunity to source talent.

6. Alignment Health: The Senior-Focused Care Concierge

Alignment Health is carving out a significant niche in the highly competitive Medicare Advantage (MA) market by building its entire model around a high-touch, concierge-style experience for seniors. Rather than competing broadly, the company focuses exclusively on delivering feature-rich MA plans designed to simplify healthcare for older adults. This strategy directly addresses a key pain point for seniors: navigating a complex system while managing chronic conditions. Serving over 100,000 members, the core of their offering is combining robust medical coverage with personalized, 24/7 support.

This senior-centric approach makes Alignment a compelling player among health insurance startups targeting specific demographics. The company offers Medicare Advantage (Part C) plans, which bundle hospital, medical, and often prescription drug coverage. A major consideration is its limited geographic footprint; Alignment Health is currently available only in select counties across Arizona, California, Nevada, North Carolina, and Texas, making ZIP code verification the first step for any potential member.

Product, User Experience, and Market Position

Alignment’s platform is designed for clarity and accessibility, a critical factor for its target audience. The member experience is anchored by a 24/7 on-demand concierge team, providing a single, reliable point of contact for everything from finding a specialist to understanding a bill. This emphasis on support is a powerful differentiator in a market often perceived as impersonal.

Key features that define the Alignment Health experience include:

• ACCESS On-Demand Concierge: A dedicated team available around the clock via phone to help members navigate their benefits, schedule appointments, and coordinate care. For example, a member can call at 10 PM to find an in-network urgent care clinic.
• The Alignment Health Card: Many plans include a pre-loaded debit card (e.g., with a $500 annual allowance) that members can use for eligible over-the-counter items, groceries, and utilities, simplifying access to supplemental benefits.
• User-Friendly Digital Tools: The website provides straightforward tools to search for in-network providers, check prescription drug coverage, and compare plan benefits based on a user's specific location.

Outreach Triggers and Strategic Insights

As a publicly traded company (NASDAQ: ALHC) focused on the rapidly growing Medicare Advantage population, Alignment Health presents numerous opportunities for strategic partners. Their consistent focus on member growth in targeted regions and investment in supplemental benefits creates clear entry points for collaboration.

For Agencies & Investors:

• Direct Mail & Local Marketing: Given its senior demographic, Alignment heavily relies on localized and direct response marketing, especially during the Annual Enrollment Period. Agencies specializing in direct mail, community events, and targeted digital ads for the 65+ audience are well-positioned to offer value.
• Benefit & Service Partnerships: The company's model is built on rich supplemental benefits. A practical example would be a non-emergency medical transportation service partnering with Alignment to become a preferred provider for members needing rides to appointments.
• Recruitment: Alignment is frequently hiring for clinical roles (like nurses and case managers), member services representatives, and market-specific sales agents. Recruiters with expertise in healthcare and insurance have a strong target for placing talent in key operational positions.

7. Sana Benefits: Modernizing Group Health for SMBs

Sana Benefits is carving out a niche by focusing on a historically underserved market: small and mid-sized businesses (SMBs). This VC-backed insurtech company, which has raised over $107 million, provides level-funded group health plans, directly challenging the expensive and complex offerings that legacy carriers typically reserve for large enterprises. Sana’s core value proposition is combining transparent, often more affordable, health plans with a modern, all-in-one administration platform for employers.

This approach makes Sana a compelling choice among health insurance startups for businesses with 2 to 500 employees who are frustrated with annual double-digit rate hikes and cumbersome administrative processes. By building its own TPA (Third-Party Administrator) and provider network relationships, Sana gains control over the member experience and cost structure. However, this focused strategy means their availability is limited to specific states, and they do not offer plans for individuals or families outside of an employer group.

Product, User Experience, and Market Position

Sana's platform is designed to alleviate the administrative burden on HR managers and business owners. The employer admin portal simplifies everything from enrollment and billing to adding or terminating employees, tasks that might otherwise require hours of paperwork and phone calls. For members, the experience is centered on accessibility and proactive care, often featuring plans with $0 virtual care options for primary, urgent, and mental health needs.

Key features that define the Sana Benefits experience include:

• All-in-One Employer Admin: A single dashboard for managing employee enrollment, billing, analytics, and member changes in real-time. An HR manager can add a new hire to the plan in minutes.
• Integrated Virtual & Low-Cost Care: Many plans include access to $0 virtual care services and partnerships with curated, low-cost labs and imaging centers. For example, members can get an MRI at a partner facility for a fraction of the typical hospital cost.
• Direct Primary Care (DPC) Access: In supported markets, Sana offers access to DPC providers, a model that fosters a stronger patient-doctor relationship outside of the traditional fee-for-service system.

Outreach Triggers and Strategic Insights

Sana's consistent funding and targeted expansion into new state markets signal a strong growth trajectory. Their focus on the SMB segment, a massive and often dissatisfied market, creates specific entry points for partners who understand the unique needs of smaller businesses. You can learn more about their growth and offerings at www.sanabenefits.com.

For Agencies & Investors:

• Broker & PEO Partnerships: Sana relies heavily on partnerships with insurance brokers and Professional Employer Organizations (PEOs) for distribution. Agencies specializing in B2B channel marketing could offer to create co-branded marketing materials and run joint webinars to educate the broker community.
• Content & Lead Generation: As they enter new markets, Sana needs to educate SMB owners on the benefits of level-funding and their unique model. Content marketing agencies can create targeted campaigns, webinars, and white papers to drive qualified leads.
• Recruitment: Sana is actively hiring for roles in sales, operations, engineering, and provider relations to support its geographic expansion. Recruiters with expertise in insurtech and B2B SaaS have a clear opportunity.

Top 7 Health Insurance Startups — Comparison

Connecting with the Insurtech Vanguard

The landscape of health insurance is undergoing a seismic shift, driven by the innovative health insurance startups we've explored. From the government-led modernization of HealthCare.gov to the gig-economy focus of Stride Health and the SMB-centric solutions from Sana Benefits, a clear pattern emerges. These companies are not merely selling policies; they are building technology-first platforms designed to enhance user experience, increase price transparency, and simplify access to care.

The profiles of Oscar Health, Devoted Health, and Alignment Health underscore a crucial trend: the consumerization of healthcare. By leveraging data analytics, AI-driven personalization, and user-friendly mobile applications, they are transforming complex, often frustrating, processes into streamlined, intuitive digital journeys. This focus on the end-user is what separates them from legacy incumbents and creates a wealth of opportunities for savvy partners. To better understand the landscape these innovators operate in, it's helpful to explore the fundamental question: What is Insurtech? This technological infusion is the core driver of the disruption we're witnessing.

Key Takeaways and Actionable Next Steps

For our audience of agencies, investors, and talent professionals, the key is to move from observation to action. The data points provided for each startup, from funding rounds to hiring velocity and ad spend, are not just trivia; they are strategic triggers.

• For Agencies (Marketing, Creative, PR): A significant funding round often precedes a major marketing push. A startup like Sana Benefits, fresh off a Series B, is likely evaluating its brand messaging, performance marketing channels, and content strategy. This is the ideal moment to present a targeted proposal showcasing your agency's expertise in scaling B2B SaaS or health-tech brands. Use their recent funding as the primary reason for your outreach.
• For Recruiters and Talent Scouts: Rapid hiring across engineering and sales departments, as seen with companies like Alignment Health, signals aggressive growth plans. This is your cue to engage. Focus your pitch on how you can help them scale their teams efficiently, highlighting your network of pre-vetted candidates in their specific tech stack (e.g., Python, React, AWS) or your track record placing enterprise sales executives.
• For Investors and VCs: While many of these companies are well-funded, tracking their early-stage competitors is crucial. Look for startups solving similar problems but for niche, underserved markets. The success of these established players validates the market need, de-risking investment in the next wave of innovators. Monitor their strategic partnerships and product expansions as indicators of future M&A activity.

Turning Insights into Opportunities

The most critical takeaway is the importance of timing. Approaching a startup with a generic pitch is ineffective. However, reaching out with a specific, data-informed solution precisely when they need it can be a game-changer. For example, noticing a spike in a company's digital ad spend could be a trigger for a performance marketing agency to offer optimization services. Observing a series of senior leadership hires on LinkedIn might be the perfect prompt for a leadership coaching or team development firm to connect.

Ultimately, the health insurance startups featured in this roundup represent the vanguard of a new era. They are well-funded, technologically sophisticated, and aggressively pursuing market share. By understanding their unique value propositions, tracking their growth signals, and aligning your outreach with their strategic needs, you can effectively partner with these market leaders and capitalize on the immense opportunities within the evolving insurtech ecosystem.

Ready to turn these insights into a pipeline of high-growth clients? FundedIQ provides the real-time funding data, hiring signals, and technology stack information you need to connect with scaling health insurance startups at the perfect moment. Stop guessing and start engaging with precision by visiting FundedIQ today.