Openly is rebuilding insurance from the ground up. We are re-envisioning and enhancing every aspect of the customer experience. Doing this requires a rapidly growing team of exceptional, curious, empathetic people with a wide range of skill sets, spanning technology, data science, product, marketing, sales, service, claims handling, finance, etc.

Now is the perfect time to join the journey. Here’s why

It’s working. We’re in multiple states and on our way to operating countrywide. We have thousands of agents selling our product and millions of dollars of annual customer premiums.
We’re well-backed & stable. We closed our $100M Series D fundraise. We are supported by some of the top investors globally, including Google’s “Gradient” AI-focused fund, Obvious Ventures, Advance Venture Partners, Eden Global Partners, and Clocktower Technology Ventures.
It’s not too late! Despite this traction and stability, we’re still early enough in the journey that there’s time to make a real difference during Openly’s formative period.

If you’d like to understand more about Openly’s mission, consider checking out this video (https://vimeo.com/267654520) from a company pitch we gave several years ago at Techstars.

Job Details

Openly is seeking an experienced Senior Director of Countrywide Insurance Product to lead our insurance product development and strategic country-wide initiatives. Reporting to the Vice President of Insurance Product Management, this pivotal role will inherit a growing highly skilled team of individuals who have driven numerous value-add initiatives to completion.

In the role, this individual will develop and scale the existing department to bring a deeper focus on the strategic direction of insurance products, develop and deliver new product features, provide analytic insights on existing in-market products, and collaborate to ensure that all product features remain in compliance with regulatory standards.

This influential position offers a unique opportunity to shape the future of our insurance products and make a significant impact on our business growth, profitability, and market position. The ideal candidate will be a visionary leader with a passion for innovation, a deep understanding of the insurance industry, and the ability to drive transformational change in a dynamic market environment.

Key Responsibilities

Product Strategy and Development: Formulate and execute a comprehensive product strategy aligned with market trends and company objectives. Lead the end-to-end development process for new insurance product features, from concept to launch.
Strategic Initiatives: Spearhead high-impact projects that drive business growth, improve operational efficiency, and enhance customer experience. Collaborate with cross-functional teams to ensure successful implementation.
Data Analytics and Insights: Oversee the insurance product analytics team in leveraging advanced data analysis techniques to inform product decisions and risk assessment models. Translate complex data into actionable business insights.
Regulatory Compliance: Ensure all insurance products and processes adhere to evolving regulatory requirements across different jurisdictions. Stay abreast of industry regulations and implement necessary changes proactively.
Coverage Forms and Documentation: Direct the development and maintenance of comprehensive, clear, and legally sound coverage forms and policy documentation. Ensure all materials effectively communicate terms, conditions, and benefits to policyholders.
Team Leadership and Development: Manage and mentor a diverse team of product managers, analysts, and specialists. Foster a culture of innovation, collaboration, and continuous improvement.
Stakeholder Management: Build and maintain strong relationships with internal stakeholders (e.g., sales, marketing, claims) and external partners (e.g., reinsurers, regulators) to ensure alignment and support for product initiatives.

Requirements

12+ years of progressive experience in insurance product development and management
A minimum of 5 years in a leadership role managing teams larger than 5-10 people and experience leading people managers
Masters degree in Business Administration, Finance, Insurance, or related field; MBA strongly preferred
Advanced analytical and problem-solving capabilities, with a data-driven approach to decision-making
Excellent leadership skills with experience managing and scaling high-performing teams
Outstanding communication and interpersonal skills, with the ability to influence at all levels of the organization
Strategic thinking with a proven ability to drive transformational change
Proven track record of successfully developing and launching innovative insurance products
Deep understanding of insurance industry trends, emerging technologies, and regulatory landscape
Strong business acumen with the ability to balance product innovation with profitability

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Compensation & Benefits:

The target salary range represents the budgeted salary range for this position. Actual compensation for this position will be determined based on the successful candidates experience and skills. We are committed to providing a compensation package that not only reflects the responsibilities and requirements of the role, but also the unique expertise that the chosen candidate will bring to our team.

Target Salary Range

$188,000—$223,250 USD

The full salary range shows the min to max salary range for this position. Actual compensation will be commensurate with experience and qualifications and determined based on various factors including the candidates qualifications, skills, and experience.

Full Salary Range

$176,250—$293,750 USD

Benefits & Perks

Remote-First Culture - We supported ## remotelife long before it was a given. Well keep promoting it.
Competitive Salary & Equity
Comprehensive Medical, Dental, and Vision Plan Offerings
Life and disability coverage including voluntary options
Competitive PTO - 20 days and 11 paid holidays (including floating holidays) per year under the Company’s vacation and holiday policies.
Parental Leave - up to 8 weeks (320 hours) of paid parental leave based on meeting eligibility requirements
(Birthing parents may be eligible for additional leave through STD)
401K Company Contribution - Openly contributes 3% of the employees gross income, even if the employee does not contribute.
Work-from-home stipend - We provide a $1,500 allowance to spend on setting up your home workplace
Annual Professional Development Fund: Each employee has $2,000 in professional development (PD) funds to spend on activities or resources annually. We want each Openly employee to achieve personal and professional success and to feel supported, confident, and informed about improving their efficiency and productivity.
Be Well Program - Employees receive $50 per month to use towards your overall well-being
Paid Volunteer Service Hours
Referral Program and Reward

Depending on position, Employees generally are eligible for cash incentive compensation, including commissions for sales eligible roles. In all cases, eligibility for compensation and benefits is subject to applicable plan and policy terms in effect from time to time.

U.S. Citizens, Green Card Holders, and those authorized to work in the U.S. for any employer and currently residing in the US will be considered.

Openly is committed to equal employment opportunity and non-discrimination for all employees and qualified applicants without regard to a persons race, color, sex, gender identity or expression, age, religion, national origin, ancestry, ethnicity, disability, veteran status, genetic information, sexual orientation, marital status, or any characteristic protected under applicable law. Openly is an E-Verify Employer in the United States. Openly will make reasonable accommodations for qualified individuals with known disabilities under applicable law.

We strive to provide an exceptional applicant and candidate journey when you engage with us. In an effort to respond to applicants in a timely manner, we leverage AI to organize applications and resumes based on required and applicable skills and experience. To allow our applicants to drive their initial interview experience with us, we may leverage an AI-supported scheduling tool so you can choose when to meet with our team. While AI assists with efficiency, all hiring decisions are made by our team members. Rest assured, your data is protected according to privacy laws and company policies. Contact our recruitment team with any questions about our AI-assisted hiring process.