Join Upland

At Upland Specialty Insurance, we take pride in building a dedicated team of “we entrepreneurs” where you can focus your experience, skills, and creativity to craft solutions for the long-term success of the company, and you as individual team member. 

Are you a “we entrepreneur”? Do you value the individual freedom to practice your craft while enjoying the benefits of working as a team? Do you like to have fun at work while being challenged? Upland may be the company for you.
Current Open Positions:
Sr. Business Development Analyst - Insurance
Remote
$80,000 - $90,000
The role of Senior Business Development Analyst will support the growth of Upland’s underwriting business as an operational service expert and advocate for the ongoing and developing needs of our underwriting teams. In this role, you will be expected to possess knowledge on existing business workflows as you will be an integral player in the development and prioritization of business initiatives. The Senior Business Development Analyst will act as a subject matter expert in their assigned lines of business and guide other Business Development Analysts and new team members in the operational procedures of the department. The Senior Business Development Analyst will support the development of requirements for Upland’s policy forms and product enhancements, rater updates and other process enhancements. In addition, the position will support established Underwriting teams and participate in the launch of new business units. This role will also act as the product owner and subject matter expert on assigned vendor products that enhance company operations.
Actuarial Analyst Intern
Remote
$20 - $22 per hour
We are seeking a motivated and detail-oriented Actuarial Intern to join our Risk, Analytics and Data team. This internship offers a unique opportunity to gain hands-on experience in actuarial reserving, working closely with seasoned professionals in the insurance industry. The successful candidate will support key reserving activities, including financial reporting, data analysis, and process improvements, while developing technical and analytical skills.
Senior Product Analyst - Risk, Analytics, and Data
Remote
$100,000 ‒ $130,000
We are looking for a Senior Product Analyst to join our Risk, Analytics and Data (RAD) team to support data, analytics, and technology initiatives involving high levels of collaboration across the organization. This role will report to the Director, Analytics Product Management.
Senior, Internal Controls
Remote
$110,000 - $130,000
The Senior, Internal Controls is responsible for helping to establish a robust Internal Audit team, including the implementation of an audit software solution, performing the annual internal controls risk assessment, and executing controls testing, including maintaining testing evidence in support of external audit and regulatory requirements. The role helps ensure risk mitigation through testing of internal controls, supports regulatory and audit readiness, and consults with SOX Director who works with business and technology partners on control design and remediation. This position is both strategic and operational, acting as a critical liaison between Finance, Risk, Governance, and Compliance functions, and plays a central role in control maturity, policy alignment, and process improvement efforts.
Director, Information Technology
Remote
$150,000 - $170,000
The Director of IT is accountable for the strategy, delivery, and continuous improvement of enterprise IT services with a primary emphasis on IT Support, asset management, identity and access management (IAM), SaaS/application administration, and third-party service delivery. This role leads IT service management practices (ITSM) practices, oversees Managed Service Providers (MSPs) and key vendors, and ensures high-quality secure, and compliant IT operations aligned to business objectives. The Director will overhaul and own operational excellence across the IT support ecosystem including incident / problem management, employee lifecycle enablement (onboarding / offboarding), asset lifecycle, and the optimization of cloud and application spend. The role partners closely with Security Operations, with Upland’s distributed IT staff across multiple departments, and business leaders to drive adoption of enterprise-grade technologies, strengthen security controls (including SSO and identity federation), and deliver a consistently exceptional end-user experience. This leader sets standards, establishes repeatable processes, and communicates clearly, producing and maintaining high-quality technical documentation and executive-ready materials that improve reliability, auditability, and stakeholder confidence.
Senior Project Manager - Insurance Data and Analytical Solutions
Remote
$100,000 - $130,000
Within our Risk, Analytics, and Data team, we focus on Actuarial, Data Science, Data and Model Engineering, and Enterprise Risk Management functions. Our vision is to build highly automated and efficient processes to build, test, and deploy our models and products for enhancing actuarial, underwriting, and claim insights with timely and relevant data-driven analytics and technology. We look to create solutions requiring creative problem solving and close collaboration with stakeholders across the organization, not limited by a ‘one size fits all’ mindset. This vision requires a high level of organization and collaboration to ensure our goals and objectives are met.