Two Chicks With A Side Hustle

🧾 About the Role
Transamerica is seeking an experienced Underwriting Trainer II to design, deliver, and manage specialized training in life, annuity, and health underwriting. You’ll lead programs that build technical expertise, enhance career development, and boost employee engagement—all while working remotely for a respected leader in financial services.


Position Highlights
• Salary: $88,000 – $110,000 annually (plus 12.5% annual bonus eligibility)
• Full-time, 100% remote
• Comprehensive benefits including medical, dental, vision, 401(k) match, pension, tuition reimbursement, and paid parental leave
• Paid Time Off starting at 160 hours in the first year, plus 10 paid holidays


📋 What You’ll Own
• Design and deliver engaging underwriting training programs using best practices in curriculum design
• Develop measurable learning criteria for various levels of underwriting expertise
• Stay current on regulations, products, and technology; share updates in group and one-on-one training
• Evaluate training effectiveness, identify skill gaps, and recommend improvements
• Create and lead career development and engagement initiatives for underwriting staff
• Collaborate on cross-functional projects that require underwriting input


🎯 Must-Have Traits
• 6+ years of underwriting experience in insurance or financial services
• Experience in underwriting training or corporate project/process management
• Exceptional written, verbal, and presentation skills
• Ability to explain technical information in an accessible way
• Strong documentation and editing skills
• Creative and collaborative approach to learning program design
• Proficiency with Microsoft Office
• Preferred: Bachelor’s in business/finance, FLMI, FALU, or CLU certification


💻 Remote Requirements
• Dedicated home office setup with reliable high-speed internet
• Ability to facilitate virtual training sessions and collaborate with distributed teams
• Availability to work a standard full-time schedule in a remote environment


💡 Why It’s a Win for Remote Job Seekers
• High-impact leadership role with a six-figure salary and generous bonus potential
• Fully remote with opportunities to shape career development programs for a national team
• Inclusive culture with employee resource groups and diversity programs
• Comprehensive health, financial, and work-life balance benefits
• Career stability at a company with over 100 years of history and global reach


✍️ Call to Action
If you’re a skilled underwriting professional ready to inspire and develop the next generation of talent, join Transamerica’s mission to help people create the financial freedom to live life on their terms. Apply today to make your mark—without leaving your home office.


Happy Hunting,

~ 2 Chicks

APPLY HERE