About CharterUP. CharterUP is transforming the $30 billion group transportation industry with cutting-edge technology and innovative SaaS software, delivering an industry-leading experience for both customers and operators. Trusted by most Fortune 500 companies, our platform connects users to thousands of charter bus and minibus operators nationwide. In just 60 seconds, customers can access real-time availability, transparent pricing, and detailed vehicle options—whether organizing a corporate event, a company shuttle, or a wedding. By streamlining what was once a fragmented and stressful process, CharterUP brings transparency, accountability, and efficiency to an industry overdue for innovation
With CharterUP, group transportation is no longer a hassle but an elevated, reliable experience. Join us as we lead the future of group travel.
Why Join Us
- Innovative Impact: Be part of the team that's revolutionizing group travel, setting new standards in an industry overdue for change.
- Growth Opportunities: As a hyper growth company and one of the fastest-growing companies recognized by Inc., there’s no better time to join our dynamic, growth-stage organization.
- Driven Team: Collaborate with some of the most driven minds in tech, all while working in a remote-first environment with a tech hub in Austin, TX.
- Funding and Stability: Our $60 million Series A funding was just the start—we’re poised for even greater expansion, and you can be part of this exciting journey. CharterUp has achieved this growth profitability and efficiently, ensuring long-term stability.
About the Role
Title: Head of New Product (Insurance)
Reports to: President
Location: Remote, US (Hybrid in Miami, Austin, Atlanta, or Denver Preferred)
CharterUP is hiring a high-impact operator to lead the launch of our first major product expansion: a captive insurance offering for our network of charter bus operators. Reporting directly to our President, you’ll take full ownership of the product from strategy through execution—building a business that directly improves the economics for hundreds of small transportation companies. This is a zero-to-one leadership role for someone who thrives on building from scratch, navigating ambiguity, and delivering outcomes. You’ll define the playbook, launch in key markets, and scale the product across our growing supply base. If you’re looking to build something that matters—with full executive backing—this is it.
What You’ll Do
- Design and launch a captive insurance product that lowers premiums and improves access for CharterUP’s operator network.
- Define the product architecture: pricing model, risk approach, distribution strategy, carrier/broker relationships, and compliance framework.
- Own go-to-market strategy: test in initial markets, iterate quickly, and scale adoption with clear traction goals in the first 6–12 months.
- Deeply understand the customer using data, interviews, and behavioral insights to validate product-market fit and iterate the offering.
- Navigate state-level licensing and regulatory requirements: obtain (or be willing to obtain) an insurance broker license.
- Operate like a founder: set goals, make fast decisions, and own every piece of execution from concept to growth.
- Build the foundation for future value-added products for operators, such as fuel cards or financing solutions.
What You’ll Bring
- Master of Business Administration (MBA) with 2–4 years of experience working with a top-tier consulting firm or investment bank.
- A strategic generalist with strong business judgment and a bias for action—you bring structure to complexity and move fast.
- Resourceful and tenacious—you break down walls, solve tough problems, and take ownership without waiting for permission.
- Comfortable navigating regulated industries—able to manage legal, compliance, and external partner dynamics.
- Experience in insurance, fintech, marketplaces, or mobility is a plus—but not required.
- Willing to pursue and obtain an insurance broker license (CharterUP will sponsor the training).
- Motivated to launch a financially impactful product that directly supports small business owners.
- Willingness to travel.
Recruiting Process
- Step 1 - Video call: Talent Acquisition interview
- Step 2 - Video call: Hiring Manager interview
- Step 3 - Video call: Team interviews
- Step 4 - Offer & reference check
- Welcome aboard!
Benefits & Perks
We take care of our team so you can focus on doing your best work. At CharterUP, you'll get:
- Remote Flexibility – Work from any of our 19 live/work states, with role-dependent exceptions
- Full Health & Wellness Coverage – 100% of premiums paid for medical, dental, and vision plans for employees - including mental health resources, Teledoc, gym discounts, and family planning benefits
- Time to Recharge – 15 days PTO (increases to 20 after 2yrs) + 8 paid holidays so you can actually unplug
- Financial Security – Company-provided life insurance, as well as short-term and long-term disability for employees who qualify
- Winning Culture – Join a high-performing, fast-paced, and supportive team that wins together
- Referral Bonuses – Get rewarded for bringing top talent to the team
- Future Planning – 401(k) retirement plan to help you invest in what’s next
- Tech Setup – Your choice of Mac or PC laptop, plus monitor, keyboard, and mouse.
CharterUP is an Equal Opportunity/Affirmative Action Employer. We make all employment decisions including hiring, evaluation, termination, promotional and training opportunities, without regard to race, religion, color, sex, age, national origin, ancestry, veteran status, sexual orientation, physical handicap, mental disability, medical condition, disability, gender or identity or expression, pregnancy or pregnancy-related condition, marital status, height and/or weight.
CharterUP candidates and employees must reside in any of the following states; Arizona, California, Colorado, Florida, Georgia, Hawaii, Mississippi, Missouri, North Carolina, New Hampshire, Nevada, New York, Oklahoma, South Dakota, Tennessee, Texas, Utah, Washington, and Wyoming.
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