Job Description

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.”

As an Excess and Surplus (E&S) carrier, we face unique and interesting problems every day. We are seeking an experienced HR Generalist to join our growing organization.

Primary Function:

We are seeking an experienced Senior HR Generalist to join our dynamic, remote first rapidly growing organization. Our workforce is distributed across multiple U.S. states, and we have a growing international footprint. The ideal candidate has strong generalist skills, is highly adaptable, and thrives in a virtual environment.

This is a hybrid role, working three days onsite at our office in Westwood, two days remote.

Duties and Responsibilities:

• Serve as primary HR point of contact for remote employees across several states, advising on local, state, and federal employment regulations
• Support all aspects of the employee lifecycle, including onboarding, benefits administration, performance management, employee relations, and offboarding
• Ensure compliance with multi-state employment laws and company policies
• Partner with managers and leaders to resolve employee issues and support a positive work culture in a remote setting
• Process and track documentation for international hiring, including work visa applications (H-1B, L-1, O-1, etc.) and support global mobility initiatives
• Collaborate with payroll, legal, and external vendors to execute cross-border employment processes
• Assist in developing and implementing HR programs that enhance employee engagement and support organizational objectives
• Maintain records in HRIS consistent with compliance standards for U.S. and international employees
• Other duties as assigned by leadership

Experience, Education, Special Skills Required:

• Bachelor’s degree in Human Resources, Business Administration, or related field
• Minimum 5 years’ experience in HR generalist roles within medium to large organizations with diverse workforce in multi-state platform and international presence
• Demonstrate knowledge of multi-state employment law, HR compliance, and remote workforce management
• Experience supporting international employees and managing work visa processes (e.g., H-1B, L-1, O-1)
• Strong interpersonal, organizational, and communication skills with the ability to work effectively across virtual teams
• Proficient in HRIS systems, MS Office Suite, and collaboration tools (Teams, etc.)
• High level of discretion, confidentiality and professionalism

Preferred Qualifications:

• PHR, SPHR, or SHRM-CP/SCP certification
• Experience in international mobility, expatriate support, and global HR operations
• Advanced proficiency in HR analytics and remote onboarding tools

Disclosures:

Pay Estimate: $80,000 - $95,000/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: September 19, 2025

Hybrid work schedule

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