Director of Operations | SimplyInsured | Remote (United States)
Posted 2025-09-08
Remote, USA
Full Time
Immediate Start
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">At SimplyInsured we are on a mission to eliminate fear in health insurance.</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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 Intuit 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.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Job Summary:</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">We’re hiring a Director of Operations who can efficiently engage and manage our amazing team of managers, team leaders, and team members and provide an exceptional experience for our customers. With thousands of interactions with customers on a monthly basis, it is critical to ensure the team is performing at the highest level of quality and productivity.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">This position will require a strong bias to action to resolve issues with urgency, the ability to leverage data to make decisions and improve processes, and exceptional leadership experience. The role will work closely with and report to the Chief Operating Officer. As the leader of the front-line team, you will use your experience in motivation, coaching, and data analysis to keep the team focused on the targets and producing at a high level, matched with high quality.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">What You’ll Do:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Continuously evaluate and improve operational processes to enhance efficiency and quality, with a specific emphasis on optimizing the customer journey to improve conversion and retention rates and to deliver outstanding customer satisfaction</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Utilize data-driven insights to inform decision-making and identify opportunities to optimize conversion funnels and reduce churn rates</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Build customer loyalty by assessing and driving strong net promoter and customer satisfaction scores across the customer experience</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Develop and execute strategies to reduce customer churn rates, including implementing proactive customer success initiatives and addressing root causes of churn</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Build and lead a high-performing team of digital operations professionals, providing mentorship, guidance, and support for their career development</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Collaborate closely with departments such as Product and Partnerships to ensure seamless integration and alignment of digital operations with overall business functions.</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">What You’ll Bring:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">8+ years of experience as a leader of operational teams in a fast-paced digital environment</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">2+ years as a manager in an operations role at at early-stage startup</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Strong problem-solving and leadership to motivate teams to solve problems with pace and urgency</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Skilled with Customer Service platforms and technologies (eg. Salesforce)</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Strong leadership and people management skills</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Process and efficiency expert with a knack for identifying bottlenecks and finding shortcuts</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">A self-motivated and proactive team player, working quickly and accurately under pressure and time constraints, with minimal supervision</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Passion for helping people – especially when it comes to their health</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Clear communicator, thoughtful listener, and highly perceptive</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Analytical skills, including expertise with spreadsheet analysis</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">High attention to detail and orientation toward building repeatable and measurable processes</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">If you’re excited to play a pivotal role in steering a cutting-edge platform’s evolution, driving collaboration across diverse teams, and employing your prowess in frontend and backend technologies, we encourage you to apply. Your expertise will directly contribute to our mission of delivering an exceptional consumer-facing product in a dynamic startup environment.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">What we offer:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Generous stock option packages</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Competitive compensation</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">“Take what you need” time off plan</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">100% Medical, Dental, and Vision Insurance coverage</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">FSA plan</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">401k</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">A values-based culture that invests in employee success</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Compensation:</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">The base salary range for this position is $140,500 to $160,000.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">We have a market-based compensation structure. The salary for this position may vary based on a candidate’s experience, industry expertise, technical skills, and location. The range provided is just one component of total compensation including, but not limited to bonus eligibility based upon the achievement of performance objectives and company stock options.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Our Culture:</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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!</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><em>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.</em></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><em>#LI-Remote</em></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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 Intuit 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.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Job Summary:</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">We’re hiring a Director of Operations who can efficiently engage and manage our amazing team of managers, team leaders, and team members and provide an exceptional experience for our customers. With thousands of interactions with customers on a monthly basis, it is critical to ensure the team is performing at the highest level of quality and productivity.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">This position will require a strong bias to action to resolve issues with urgency, the ability to leverage data to make decisions and improve processes, and exceptional leadership experience. The role will work closely with and report to the Chief Operating Officer. As the leader of the front-line team, you will use your experience in motivation, coaching, and data analysis to keep the team focused on the targets and producing at a high level, matched with high quality.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">What You’ll Do:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Continuously evaluate and improve operational processes to enhance efficiency and quality, with a specific emphasis on optimizing the customer journey to improve conversion and retention rates and to deliver outstanding customer satisfaction</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Utilize data-driven insights to inform decision-making and identify opportunities to optimize conversion funnels and reduce churn rates</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Build customer loyalty by assessing and driving strong net promoter and customer satisfaction scores across the customer experience</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Develop and execute strategies to reduce customer churn rates, including implementing proactive customer success initiatives and addressing root causes of churn</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Build and lead a high-performing team of digital operations professionals, providing mentorship, guidance, and support for their career development</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Collaborate closely with departments such as Product and Partnerships to ensure seamless integration and alignment of digital operations with overall business functions.</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">What You’ll Bring:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">8+ years of experience as a leader of operational teams in a fast-paced digital environment</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">2+ years as a manager in an operations role at at early-stage startup</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Strong problem-solving and leadership to motivate teams to solve problems with pace and urgency</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Skilled with Customer Service platforms and technologies (eg. Salesforce)</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Strong leadership and people management skills</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Process and efficiency expert with a knack for identifying bottlenecks and finding shortcuts</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">A self-motivated and proactive team player, working quickly and accurately under pressure and time constraints, with minimal supervision</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Passion for helping people – especially when it comes to their health</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Clear communicator, thoughtful listener, and highly perceptive</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Analytical skills, including expertise with spreadsheet analysis</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">High attention to detail and orientation toward building repeatable and measurable processes</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">If you’re excited to play a pivotal role in steering a cutting-edge platform’s evolution, driving collaboration across diverse teams, and employing your prowess in frontend and backend technologies, we encourage you to apply. Your expertise will directly contribute to our mission of delivering an exceptional consumer-facing product in a dynamic startup environment.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">What we offer:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Generous stock option packages</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Competitive compensation</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">“Take what you need” time off plan</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">100% Medical, Dental, and Vision Insurance coverage</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">FSA plan</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">401k</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">A values-based culture that invests in employee success</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Compensation:</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">The base salary range for this position is $140,500 to $160,000.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">We have a market-based compensation structure. The salary for this position may vary based on a candidate’s experience, industry expertise, technical skills, and location. The range provided is just one component of total compensation including, but not limited to bonus eligibility based upon the achievement of performance objectives and company stock options.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Our Culture:</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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!</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><em>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.</em></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><em>#LI-Remote</em></p>