The Mission: Eliminate Fear

Health insurance is complicated, expensive, and intimidating. At SimplyInsured, we are on a mission to eliminate that fear. We empower small business owners—the backbone of the economy—by making the enormous task of providing health insurance transparent, accessible, and dead-simple.

Born in Y-Combinator and backed by top-tier investors like Polaris Partners and Bessemer Venture Partners, we are disrupting a convoluted industry through massive partnerships with NetSuite, Toast, and Square.

The Role: The Growth Engine

As our Senior Strategic Partnerships Manager, you will report directly to the CEO and serve as the face of SimplyInsured to our most valuable allies. You aren't just "managing accounts"; you are an architect of revenue. You will be responsible for nurturing our existing ecosystem—including major platforms like Toast and Square—while identifying and unlocking new revenue streams through creative co-marketing and deep-funnel integrations.

This is a high-visibility role for a proactive relationship-builder who thrives on hitting growth targets and building long-term value.

How You’ll Make an Impact

• Drive Revenue & Growth: Own the commercial success of our key partnerships. You’ll develop and execute strategic account plans designed to increase user acquisition and maximize the value of every partnership.
• Be the Primary Envoy: Act as the main point of contact for executive stakeholders at our partner companies, ensuring SimplyInsured is their "top-of-mind" health insurance solution.
• Full Lifecycle Ownership: Manage the journey from initial onboarding and technical integration to post-launch optimization and long-term scaling.
• Strategic Co-Marketing: Partner with marketing teams to design and launch high-impact campaigns (webinars, email journeys, landing pages) that resonate with small business owners.
• Data-Driven Strategy: Track KPIs, conduct quarterly business reviews (QBRs), and synthesize partner feedback into actionable insights for our Product and CEO.
• Spot Opportunities: Identify "white space" within existing accounts to expand our footprint within their ecosystem.

What You’ll Bring

• The Track Record: 5+ years of experience in Strategic Partnerships with a proven history of hitting revenue targets in an early-stage startup or high-growth SaaS environment.
• The "Hustle" Factor: You are a self-starter who doesn't wait for a playbook—you write it.
• The Communicator: Exceptional presentation skills. You can take the "convoluted world of insurance" and make it sound simple and exciting to a partner.
• Analytical Rigor: You are comfortable with data and can use it to tell a story that justifies a new experiment or resource allocation.
• Insurtech/Fintech Knowledge: (Preferred) Experience navigating the complexities of regulated industries.

What We Offer

• Equity Stake: Generous stock option packages—you should benefit from the growth you drive.
• Competitive Pay: Strong base salary plus an annual performance bonus up to 25% of your annual base salary based on partner retention and revenue growth. 
• Comprehensive Benefits: 100% Company-paid Medical, Dental, and Vision for you and your family members.
• Freedom & Trust: "Take what you need" time off and a remote-first culture that values results over "clocking in."
• Direct Impact: A reporting line to the CEO and a culture that values "the obligation to dissent."

Compensation

Starting Base Salary Range: $110,000 - $150,000  ($130-$190,000 OTE) 

A Note on Our Inclusive Culture

SimplyInsured is driven by the diversity of our backgrounds. Statistics in the tech industry show that underrepresented groups—including women and people of color—often hesitate to apply unless they meet 100% of the qualifications.

If you are passionate about our mission and have the "startup grit" we're looking for, please apply. We value unique perspectives and are looking for someone to amplify our team, not just fit into it.

#LI-Remote  #LI-HS1

At SimplyInsured we are on a mission to eliminate fear in health insurance.

Health insurance is complicated, expensive, and really important - so it tends to create fear for most people; our goal is to reduce that fear as much as possible. 

We specifically work with small business owners who have the enormous task of purchasing the right type of insurance for their employees and their families. With more than 20,000 customers and several major partnerships, including NetSuite, Toast, and Square, we're growing quickly and disrupting this convoluted and confusing industry by making it more transparent and fully accessible to everyone. We got our start in the Y-Combinator incubator, and have been funded by top-tier investors at Polaris Partners, Bessemer Venture Partners, New York Life Ventures and AltaIR Capital. 

Job Summary: 

As a Client Outreach Coordinator you will work with our Client Operations team to ensure all of SimplyInsured’s customers are properly submitted and enrolled with their requested Insurance Carrier and the SimplyInsured platform. This role is integral to providing outstanding service to our customers and ensuring a smooth onboarding process. 

What you’ll do:

• Support the onboarding process of new groups from application through to successful enrollment 
• Work with customers on their annual benefits renewal process and any coverage or carrier changes
• Utilize phone, text, and email to provide proactive onboarding support and reconcile issues for customers 
• Partner with internal team members in revenue operations and support to ensure a smooth, high-satisfaction experience for customers 
• Keep detailed notes/records in Salesforce regarding customer accounts and interactions

What you’ll bring:

• 1-2 years of experience in customer service or sales role
• A Life and Health Insurance license or the ability to obtain one within 3 months of employment. 
• Positive and optimistic personality and strong customer empathy and focus 
• Highly productive with good multitasking skills
• Able to work in a high-volume work across channels and tasks 
• Previous experience with Salesforce a plus! 
• Fantastic oral and written communication skills
• Strong desire to help businesses maximize their healthcare

What we offer:

• Generous stock option packages
• Hourly pay plus a quarterly performance bonus opportunity of $625
• “Take what you need” time off plan
• 100% Medical, Dental, and Vision Insurance coverage options for employees and dependents
• 401k 
• Fully remote environment 
• Flexible schedule options between the hours of 7am-6pm CST Monday-Friday. 
• A values-based culture that invests in employee success

Compensation:

The base salary range for this position is $16 for those who are unlicensed and $17 once you are licensed or if you already have your Life and Health insurance license. 

Our Culture:

We value radical 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. Research shows that candidates from underrepresented backgrounds often don't apply for roles if they don't meet all the criteria. We strongly encourage you to apply if you're interested; we'd love to learn how you can amplify our team with your unique experience!

We are an equal-opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

#LI-Remote

The Mission: Eliminate Fear

Health insurance is complicated, expensive, and intimidating. At SimplyInsured, we are on a mission to eliminate that fear. We empower small business owners—the backbone of the economy—by making the enormous task of providing health insurance transparent, accessible, and dead-simple.

Born in Y-Combinator and backed by top-tier investors such as Polaris Partners and Bessemer Venture Partners, we are disrupting a convoluted industry through major partnerships with NetSuite, Toast, and Square. We aren't just building a tool; we’re building the infrastructure for the future of health benefits.

As our Lead Product Manager, you will report directly to the CEO. You aren't just managing a backlog; you are the architect of our next phase of growth. You will lead the "0-1" charge for new integrated partnerships and innovative product lines that will define SimplyInsured for the next decade.

This is a high-leverage role for a veteran PM who wants the autonomy to own product strategy and solve complex problems. 

What You’ll Do

• Architect the Roadmap: Define the vision and strategy for new integrated partnerships (e.g., embedding our engine into the world's largest B2B platforms).
• Lead 0-1 Initiatives: Take raw ideas from the CEO or market feedback and turn them into validated, scalable products.
• Bridge the Gap: Act as the strategic glue between Engineering, Operations, and our high-profile external partners.
• Translate Complexity: Turn the "black box" of insurance regulations into an elegant, intuitive end-user experience that builds trust and removes fear. 
• Build the Engine: Beyond shipping features, you will refine our product discovery processes, mentorship culture, and data-driven experimentation frameworks.
• Evangelize the "Why": Present actionable insights from competitive intel and industry data to the executive team to pivot or double down on key bets.

What You’ll Bring

• The Experience: 7+ years in Product Management, specifically within early-stage Silicon Valley environments (Fintech, Healthtech, or Insurtech preferred).
• The "Founding" Spirit: Proven track record of taking a product from concept to launch (0-1) and scaling it to significant user/revenue milestones.
• Technical & Analytical Prowess: You are comfortable diving into API documentation one hour and SQL dashboards the next.
• High-Stakes Communication: Experience managing relationships with C-level stakeholders, both internally and at Fortune 500 partner companies.
• UX Obsession: A deep empathy for the small business owner and their employees; you understand that for our users, "simple" is a feature, not an aesthetic.

What We Offer

• True Ownership: A generous stock option package that reflects your impact as a leader in the company.
• Executive Access: A direct reporting line to the CEO and a seat at the table for major strategic decisions.
• Total Wellness: 100% Company-paid Medical, Dental, and Vision for you and your family.
• Flexibility: A remote-first environment with a "Take what you need" time off plan.
• Future-Proofing: 401k plan and a values-based culture that invests in your long-term career growth.

Compensation

Starting Base Salary Range: $170,000 - $200,000 Note: This is just one part of total compensation, which includes performance bonuses and significant equity upside.

Our Culture

We value radical transparency, a bias for action, and the obligation to dissent. We hold each other to extremely high standards because our mission—protecting families' health and finances—demands it.

SimplyInsured is an equal opportunity employer. We strongly encourage candidates from underrepresented backgrounds to apply. If you’re excited about the mission but don’t check every single box, apply anyway—we want to hear how your unique perspective can amplify our team.

The Mission: Eliminate Fear

Health insurance is complicated, expensive, and intimidating. At SimplyInsured, we are on a mission to eliminate that fear. We empower small business owners—the backbone of the economy—by making the enormous task of providing health insurance transparent, accessible, and dead-simple.

Born in Y-Combinator and backed by top-tier investors like Bessemer Venture Partners, we are disrupting a convoluted industry. We aren’t just a platform; we are a lifeline for over 20,000 customers.

The Role: The Face of the Mission

As a Customer Support Representative, you are on the front lines of our mission. You are the voice of calm in a confusing industry. You won't just be "processing tickets"—you will be guiding real people through some of the most important decisions they make for their families and employees.

This is a multi-channel role (Phone, Chat, Email) where your empathy, speed, and problem-solving skills will directly impact our growth and customer loyalty.

How You’ll Make an Impact

• Be a Trusted Guide: Help potential customers navigate our online shopping experience, helping them find the perfect health insurance quotes for their teams.
• Solve Real Problems: Resolve administrative and billing questions with urgency and clarity. Your goal is to turn a "stressful question" into a "seamless resolution."
• Master the Stack: Use industry-leading support tools and CRMs to document interactions and ensure no customer is left behind.
• Advocate for Change: You have a front-row seat to our customers’ challenges. You are empowered to propose product and process improvements directly to our leadership team.
• Deliver "Delight": Maintain high productivity in a fast-paced, high-volume environment while keeping a "people-first" attitude.

What You’ll Bring

• Experience: 1-2 years in a customer-facing role (Support, Retail, or Sales) in a remote, startup environment. 
• Communication: Exceptional oral and written skills. You can explain complex topics in a way that is easy to understand.
• Tech-Savvy: Familiarity with support ticketing systems (like Zendesk, Freshdesk, or Salesforce) and the ability to multitask across several tabs and tools.
• Empathy: A genuine passion for helping people and a desire to support small business owners.
• Reliability: Ability to work a consistent schedule of 8:30 am – 5:00 pm CST, Monday through Friday.

What We Offer

• World-Class Benefits: 100% Company-paid Medical, Dental, and Vision coverage for you and your dependents. This is a rare benefit that ensures your family is as protected as our customers.
• Work from Anywhere: This is a 100% remote position (must be based in the U.S.).
• Generous Time Off: "Take what you need" vacation policy to ensure you stay refreshed.
• Growth Culture: A values-based environment where your "obligation to dissent" and your ideas for improvement are actually heard.

Compensation

Starting Base Salary: $15.00 per hour Note: This is the base hourly rate. We offer a robust benefits package that significantly increases the total value of your compensation.

Our Commitment to Diversity

We are driven by the diversity of our backgrounds. Research shows that candidates from underrepresented backgrounds—including women and people of color—often apply only if they meet 100% of the criteria.

At SimplyInsured, we want to change that. If you are passionate about our mission and have a heart for service, we want to hear from you—even if you don't check every single box.

SimplyInsured is an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.