
SimplyInsured
We sell health insurance to small businesses 100% online.
What SimplyInsured does
SimplyInsured was founded with one mission: to eliminate fear from health insurance. By changing the way small business owners purchase health insurance with our 100% online platform, we’re transforming a $20 billion dollar industry and delighting thousands of customers. Our unique values-based culture (and extremely talented team) is our core competitive advantage, and each person on our team makes a direct, immediate impact on our business. We value transparency, feedback, bias to action, growth, and an obligation to dissent. Every opinion is respected, we hold each other to extremely high standards, we’re driven by the diversity in our backgrounds, and unified by 100% alignment on our mission. What’s best for the customer is the heart of everything we do, and our customer stories prove it: by changing health insurance we’re literally saving lives. Based in San Francisco, SimplyInsured was founded in 2012 and is back by Bessemer Venture Partners, Polaris Ventures, and Y-Combinator. If you’re up for the challenge of improving health insurance for millions of Americans, we’re just getting started, and we’re growing!
5 open roles
What the role involves
About SimplyInsured SimplyInsured is on a mission to eliminate the fear from purchasing and navigating health insurance in the United States. We specifically work with small business owners who have the enormous task of purchasing the right type of insurance for their employees and families. With more than 10,000 customers and major partnerships with Intuit and Square, we're growing quickly and disrupting this convoluted, confusing industry by making it more transparent and fully accessible to everyone. Our team’s broad experience includes founding companies; scaling successful startups like Cardpool and Domo; working in established companies like Cisco Systems, Convergys, Dell EMC, and Yahoo; consulting at Bain, McKinsey and Deloitte; and venture capital investing. We got our start in the Y-Combinator incubator, and have been funded by top tier investors at Polaris Partners, New York Life Ventures, Bessemer Venture Partners, and AltaIR Capital. We are a Series A company and have raised $10M+ in venture capital. We value radical transparency, feedback, bias to action, growth, and an obligation to dissent. Every perspective is respected and supported. We are motivated by the diversity in our backgrounds, and unified by 100% alignment on our mission. The Role We’re hiring a Senior Product Manager to join our product team and assist in taking our platform to the next level. This is an opportunity to get in at the ground level, make an impact on the product roadmap, and bridge together team members with a cross-collaborative function. This role will report to the CEO. The Senior Product Manager will work closely with our engineering, design, and operations teams to establish the direction for the future of our platform and help us serve small businesses with their insurance needs. You'll be responsible for gathering, structuring, and prioritizing product requirements from internal and external stakeholders. Execute the roadmap across our technology stack to deliver industry-leading service at scale. Serving our mission of making it effortless to understand, navigate, and pay for care. A successful person in this role will have a customer-first mindset with immense empathy and curiosity for the customer experience. They are expected to: Take customer insights and translate them into actionable requirements that our engineering team can rally behind Lead in cross-functional collaboration Gain results by utilizing influence as well as information leadership skills becoming a trust member of the company Use clear communication and advocate for the customer Operate in ambiguity and take risks to improve the overall product and customer experience Responsibilities Own the key conversion metrics for the company’s primary health insurance marketplace product Own and drive the product roadmap for our suite of member experience products Prioritize feature requests, enhancements, backlog, and opportunities based on company goals and objectives Create a deep understanding of our small business customers - who they are, how they work, and what their needs and requirements are Explore, build, and own new product lines and features - including our expansion to individual and large group health insurance Partner with sales, client success, customer experience and carrier teams to deeply understand each member needs, and deliver the best technology-driven solution to meet those needs Mentor team members by adopting our best practices Become the health insurance market expert, digging in deep with our carriers Your skills include 5 - 7 years of experience in product management or software engineering Bachelor's degree Excellent organizational skills with the ability to keep track of multiple projects simultaneously Demonstrated success in leading development of products and customer-facing features from inception to delivery. Experience with confusing customer feedback interviews and turn those into insights Excellent problem-solving, project-manag
What the role involves
We are looking for hackers and generalists who like using software to improve lives and make an impact, while tackling difficult technical problems. We are built on Ruby on Rails and React, but what's most important is solving problems and getting stuff done. As a Senior Engineer, you will have the chance to mentor less experienced engineers on the team and helping us grow. Reporting to our Head of Engineering and working closely with our Head of Product, our engineers build customer-facing tools with significant autonomy and product ownership. Our engineers are the key to our growth, and their opinions valued. SimplyInsured is a 100% online platform to buy small business health insurance. We are revolutionizing the $20B health insurance brokerage market and improving our customers' lives. We have thousands of delighted customers, grow in double digits every month, and are backed by YCombinator and some of Silicon Valley’s top entrepreneurs and investors.
What the role involves
About SimplyInsured SimplyInsured is on a mission to eliminate the fear from purchasing and navigating health insurance in the United States. We specifically work with small business owners who have the enormous task of purchasing the right type of insurance for their employees and families. With more than 17,000 customers and major partnerships with Intuit and Square, we're growing quickly and disrupting this convoluted, confusing industry by making it more transparent and fully accessible to everyone. Our team’s broad experience includes founding companies, scaling successful startups like Cardpool and Domo; working in established companies like Cisco Systems, Convergys, Dell EMC, and Yahoo; consulting at Bain, McKinsey, and Deloitte capital investing. We got our start in the Y-Combinator incubator and have been funded by top-tier investors at Polaris Partners, New York Life Ventures, Bessemer Venture Partners, and AltaIR Capital. We are a Series A company and have raised $10M+ in venture capital. We value radical transparency, feedback, bias to action, growth, and an obligation to dissent. Every perspective is respected and supported. We are motivated by the diversity in our backgrounds and unified by 100% alignment on our mission. The Role SimplyInsured is looking for a full-time quality assurance engineer who will work closely with our engineering and product teams to help drive the quality assurance process and support our release cycles. In this hands-on role, you will be the go-to person for testing to ensure we consistently deliver a high-quality product to our community of small businesses. Responsibilities Oversee planning and the implementation of well thought out and scalable quality assurance strategies Create new test cases/test plans, and keep existing test documentation up to date Execute manual quality assurance processes throughout various development phases (regression, exploratory testing, new feature testing, etc.) to ensure delivery of predictable, high-quality product releases Work with a close-knit team to identify trends, bugs, and triage priorities Build out our automated testing suite to identify regressions and verify the correctness of our apps Collaborate with Product to gain expert knowledge about our user experience and domain Enhance developer productivity and efficiency as we scale to support many more customers and functions Create detailed, reproducible bug reports Influence key go/no go decisions on mobile and web releases Be a champion of quality in every phase of the development process Your skills include At least 2 years of experience in a quality assurance role Ability to create test cases, define testing strategies, and identify high-risk areas Ability to identify and prioritize bugs Proficiency in Atlassian Jira /ConfluenceObsessive attention to detail and product quality Self-motivation and a deep sense of pride in your work Passion for problem-solving and the right attitude/aptitude for learning new technology in a fast-paced environment Excellent written and verbal skills Benefits and Perks We're currently working from home due to Covid-19, and the following don't apply until we're safely back in the office: Team Outings (in-person), Offsite Retreats Every 6 months (in-person), Dog-Friendly Offices, Collaborative Office Space, and Stocked Kitchen Competitive compensation Generous stock option packages Take what you need - time off plan 100% Medical, Dental, and Vision Insurance coverage FSA plan 401k A values-based culture that invests in employee success Regarding COVID-19 With the spread of COVID-19, SimplyInsured offices will remain closed until further notice with the exception of employees who require access. Our primary concern is for the health and well-being of our employees as well as candidates. We have transitioned all interviews and onboarding to be conducted virtually. We are an equal opportunity employer and value diversity at our company. We do not disc
What the role involves
About SimplyInsured SimplyInsured is on a mission to eliminate the fear from purchasing and navigating health insurance in the United States. We specifically work with small business owners who have the enormous task of purchasing the right type of insurance for their employees and families. With more than 17,000 customers and major partnerships with Intuit and Square, we're growing quickly and disrupting this convoluted, confusing industry by making it more transparent and fully accessible to everyone. Our team’s broad experience includes founding companies, scaling successful startups like Cardpool and Domo; working in established companies like Cisco Systems, Convergys, Dell EMC, and Yahoo; consulting at Bain, McKinsey, and Deloitte capital investing. We got our start in the Y-Combinator incubator and have been funded by top-tier investors at Polaris Partners, New York Life Ventures, Bessemer Venture Partners, and AltaIR Capital. We are a Series A company and have raised $10M+ in venture capital. We value radical transparency, feedback, bias to action, growth, and an obligation to dissent. Every perspective is respected and supported. We are motivated by the diversity in our backgrounds and unified by 100% alignment on our mission. The Role SimplyInsured is looking for a full-time quality assurance engineer who will work closely with our engineering and product teams to help drive the quality assurance process and support our release cycles. In this hands-on role, you will be the go-to person for testing to ensure we consistently deliver a high-quality product to our community of small businesses. Responsibilities Oversee planning and the implementation of well thought out and scalable quality assurance strategies Create new test cases/test plans, and keep existing test documentation up to date Execute manual quality assurance processes throughout various development phases (regression, exploratory testing, new feature testing, etc.) to ensure delivery of predictable, high-quality product releases Work with a close-knit team to identify trends, bugs, and triage priorities Build out our automated testing suite to identify regressions and verify the correctness of our apps Collaborate with Product to gain expert knowledge about our user experience and domain Enhance developer productivity and efficiency as we scale to support many more customers and functions Create detailed, reproducible bug reports Influence key go/no go decisions on mobile and web releases Be a champion of quality in every phase of the development process Your skills include At least 2 years of experience in a quality assurance role Ability to create test cases, define testing strategies, and identify high-risk areas Ability to identify and prioritize bugs Proficiency in Atlassian Jira /ConfluenceObsessive attention to detail and product quality Self-motivation and a deep sense of pride in your work Passion for problem-solving and the right attitude/aptitude for learning new technology in a fast-paced environment Excellent written and verbal skills Benefits and Perks We're currently working from home due to Covid-19, and the following don't apply until we're safely back in the office: Team Outings (in-person), Offsite Retreats Every 6 months (in-person), Dog-Friendly Offices, Collaborative Office Space, and Stocked Kitchen Competitive compensation Generous stock option packages Take what you need - time off plan 100% Medical, Dental, and Vision Insurance coverage FSA plan 401k A values-based culture that invests in employee success Regarding COVID-19 With the spread of COVID-19, SimplyInsured offices will remain closed until further notice with the exception of employees who require access. Our primary concern is for the health and well-being of our employees as well as candidates. We have transitioned all interviews and onboarding to be conducted virtually. We are an equal opportunity employer and value diversity at our company. We do not disc
What the role involves
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Company facts compiled from public sources and last refreshed 9 September 2026. Details change; treat the company’s own site as the authority.