Upland Capital Group, Inc. is an AM Best rated “A-” VIII specialty property/casualty insurer headquartered in Dallas, Texas. Through its wholly owned insurance carrier, Upland Specialty Insurance Company, the company markets, underwrites and services specialty insurance products in select markets to include excess transportation, construction casualty, excess casualty, primary general liability, excess public entity, professional liability errors and omissions as well as excess cyber liability.  

We focus on “old school” underwriting as a craft, add “new school” analytics and technology, and encourage a gritty, growth mindset among people called “we entrepreneurs.”

Within our Risk, Analytics, and Data (RA&D) 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.

As an Excess and Surplus (E&S) carrier, we face unique and interesting problems every day. We are seeking a Senior Project Manager to join our Risk, Analytics & Data team.

Duties and Responsibilities:

• Work directly with actuarial, underwriting, operations, and claims to manage individual projects or sub projects of larger initiatives
• Work across the organization to build strong working relationships, deliver project results, and improve existing or create efficient work processes

Tooling and Process Governance

• Project Management (PM) Tools – serve as dept expert (Monday.com, Jira, Confluence)
• Develop RAD best practices and collaborate with UW Ops for potential input
• Help structure PM tools for best results rolling up to OKRs
• Form consultative relationships with teams to assist in ensuring work and process in PM tools is followed
• Ensure work is flowing properly to other tools
• Ensure PM tool process is defined and followed
• Ensure business process is documented, easy to follow, and RAD knows where located and how to utilize

OKRs

• Co-develop straightforward OKR process for RAD
• Ensure business process is documented, easy to follow, and RAD knows where located and how to utilize
• Assist in drafting OKR ppts, scheduling team sessions for follow up, ensure ppts are done in advance

Artificial Intelligence

• Basic understanding or exposure to AI tools, including ChatGPT and Claude Anthropic. This role will help develop automation to reduce administrative work in the context of managing projects

Support the overall execution of the Rating Platform effort, focusing on 3 areas:

Planning and coordination

• Coordinate quarterly planning logistics and ensure all teams enter planning with ready backlogs and clear capacity inputs
• Facilitate alignment on objectives, scope, dependencies, and risks before and during quarterly planning
• Support Product Owner in sequencing work by providing visibility into delivery constraints, integration needs, and team readiness
• Drive creation of milestones, feature timelines, and dependency maps for the Rating Platform

Cross-team alignment

• Lead weekly execution syncs to ensure the rating platform teams remain aligned on progress, risks, and blockers
• Maintain a unified delivery view ensuring Product, BA, and Engineering have shared visibility
• Track commitments, sprint progress, release timelines, and integration points to ensure on-time delivery
• Manage escalation of cross-team issues and ensure fast resolution with stakeholders

Risk and dependency tracking

• Identify technical, data, and process dependencies early and coordinate resolution with the appropriate stakeholders
• Maintain a structured risk log that captures delivery risks, mitigation plans, and accountability owners
• Facilitate conversations between SMEs, engineering teams, and product lines to unblock feature delivery
• Support the execution of various department projects and strategies when needed
• Other duties as assigned

Experience, Education, Special Skills Required:

• Bachelor's degree preferred but not required (5 years of experience required in lieu of degree)
• 3+ years of project management experience, ideally within the P&C insurance industry or related fields
• Proficient with workflow and PM tools (e.g., Jira, Monday.com) and documentation tools (e.g., Confluence)
• Exposure or working knowledge of AI tools and understanding tool capabilities
• Experience working with data, analytics, and model engineering teams
• Experience working cross-functionally across business and technical teams, including very strong ability to build solid working relationships and deliver results
• Excellent verbal and written communication skills, especially with non-technical users
• Strong critical thinking and structured problem-solving skills
• High attention to detail, organization, and follow-through
• Self-starter, quick learner, and creative problem solver that thrives in a flexible, fast paced, and remote work environment 

Disclosures:

Pay Estimate: $100,000 - $130,000/year

Other compensation: annual incentive program

Benefits: health insurance including FSA and HSA options and free access to Teladoc, vision, dental, disability and life insurance, parental leave, responsible time off (unlimited vacation days without an accrual system), paid sick time as required by law, 401(k), tuition reimbursement and employee assistance program.

Anticipated close date: January 30, 2026