Full-Time

Lead Sales Trainer

Retirement Plans

Updated on 8/1/2026

Transamerica

Transamerica

10,001+ employees

Financial services and longevity planning

Compensation Overview

$100k - $120k/yr

+ 12.5% annual bonus

Philadelphia, PA, USA + 3 more

More locations: Denver, CO, USA | Cedar Rapids, IA, USA | Baltimore, MD, USA

Hybrid

Three days in the office per week are required; occasional travel is less than 10%.

Category
Training
Required Skills
SharePoint
Microsoft Office
Word/Pages/Docs
Quality Assurance (QA)
Excel/Numbers/Sheets
Microsoft Outlook
PowerPoint/Keynote/Slides

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Requirements
  • A bachelor's degree in a business field or equivalent experience is required.
  • Seven years of learning and development experience are required.
  • Deep industry and product knowledge in specialty areas based on business need, such as retirement, mutual funds, annuities, life insurance, and employee benefits, is required.
  • Knowledge of adult learning principles is required.
  • Advanced documentation and technical writing skills are required.
  • Strong communication and interpersonal skills are required.
  • Excellent customer service skills and the ability to work both on a team and independently are required.
  • The ability to incorporate creative and innovative solutions in a learning environment is required.
  • Project management skills are required.
  • Advanced proficiency using Microsoft Office tools is required.
Responsibilities
  • Define, create, and deliver training programs to meet the learning and development needs of the business units, including developing instructor materials and assessments specific to training requirements.
  • Lead the design and development of new-hire training and facilitate program delivery to virtual and external regional vice presidents, internal wholesalers, sales desk assistants, account managers, and other sales personnel for each product.
  • Provide ongoing training in response to new products, systems, and processes, and provide supplementary and review training as needed.
  • Design, develop, and facilitate ongoing training for continual improvement of sales skills, including relationship selling, decision-making styles, and customer-centric language.
  • Design, develop, and facilitate leadership-development training for management across distribution channels.
  • Identify appropriate content to implement using learning management systems and evaluate existing content for development of e-learning modules and programs.
  • Mentor trainers to develop their skills, knowledge, and proficiency; conduct informal quality assurance through peer review and attendance at offered training programs; and share best practices, successes, and innovations to advance team performance.
  • Evaluate participant and manager evaluations to measure training effectiveness, focusing on long-term behavioral implementation and business impact.
  • Provide focused training to selected groups as requested.
  • Attend meetings with the Sales Desk team, assistant vice presidents, marketing partners, and vendors to develop sales strategies, materials, and messaging supporting products and services.
  • Support development of a learning and development bench of talent through training, coaching, and mentoring, primarily for candidates identified from the internal sales desk.
  • Work in a hybrid office environment with three days in the office and occasional travel of less than 10%.
Desired Qualifications
  • Training experience in the financial services industry, particularly qualified retirement plans.
  • Certified Professional in Learning and Performance or Certified Retirement Plan Specialist certification.
  • Instructional design experience.
  • Knowledge of computer application software such as Microsoft Office, Outlook, Word, Excel, PowerPoint, SharePoint, and Copilot.

Transamerica helps financial professionals, brokers, agents, advisors, and employers design and deliver financial plans that adapt to longer lifespans. It provides life and retirement solutions distributed through its network (Transamerica Capital, Inc.) to empower clients and employees to pursue their goals at every stage of life. Its products work by using advisor-led planning and tailored financial solutions to cover life events, retirement, and ongoing financial needs across multiple stages. The company differentiates itself by focusing on longevity planning and multi-stage life planning through a broad advisor and employer distribution network, and by offering a suite of products designed to help people take control of their financial future. Its goal is to help people live their best life by providing guidance and products that support financial security as life stages extend.

Company Size

10,001+

Company Stage

N/A

Total Funding

N/A

Headquarters

Baltimore, Maryland

Founded

1904

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Simplify Jobs

Simplify's Take

What believers are saying

  • Constructive GDP and earnings views support retirement and investment messaging.
  • Investment-grade credit and stocks benefit from Transamerica's favorable entry-point thesis.
  • Rate-cut expectations support demand for fixed-income and retirement guidance.

What critics are saying

  • Leadership turnover in investment management can unsettle clients during volatile markets.
  • Higher-for-longer rates pressure bond returns and fee-sensitive retirement assets.
  • A market drawdown would damage equities, credit marks, and retirement-plan sentiment.

What makes Transamerica unique

  • Transamerica pairs retirement products with CIO-led market outlook content and commentary.
  • Andrew Yorks became chief investment officer in October 2025.
  • The firm frames volatility around earnings, rates, and asset allocation, not panic.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

401(k) Company Match

Pension Plan

Employee Stock Purchase Plan

Tuition Reimbursement

Paid Vacation

Paid Sick Leave

Paid Holidays

Parental Leave

Adoption Assistance

Employee Assistance Program

Wellness Program

Flexible Work Hours

Paid Time Off

Employee Discounts

Career Training & Development Opportunities

Employee Matching Gifts Program

Referral Bonus Programs

Inclusion and Diversity Programs

Employee Resource Groups

Growth & Insights and Company News

Headcount

6 month growth

3%

1 year growth

3%

2 year growth

3%
Gray Media
Apr 9th, 2026
Fewer than 25 Iowa employees laid off from Transamerica.

Fewer than 25 Iowa employees laid off from Transamerica. Published: Apr. 9, 2026 at 10:20 AM PDT | Updated: 32 minutes ago CEDAR RAPIDS, Iowa (KCRG) - Transamerica said "fewer than 25 employees" were impacted by layoffs in Iowa, a media relations spokesperson told KCRG Thursday. Transamerica is a life insurance and financial services company with a location in Cedar Rapids. The company said the positions were eliminated as it is transitioning to a new retirement operations model. Transamerica said its Cedar Rapids location remains its largest office and a key hiring hub. The company is headquartered in Baltimore. KCRG reached back out requesting additional details about when the workers were notified, if any of them are still working and if any positions would be relocated. A Transamerica spokesperson replied that there is no additional information to share at this time.

401(k) Specialist
Mar 16th, 2026
Transamerica Launches AI-Powered 'Pearl' to Speed Retirement Plan Rollovers

Transamerica launches ai-powered 'Pearl' to speed retirement plan rollovers. New virtual assistant combines AI, data, and human support to help participants consolidate retirement accounts in days instead of weeks March 16, 2026 Consolidating retirement accounts in days instead of weeks is the goal of "Pearl, The Transamerica Virtual Assistant," introduced by the company today. Pearl is a new, purpose-built digital experience that brings together AI, data and human support in a single, continuous workflow - designed to help retirement plan participants move savings from other retirement accounts into Transamerica with greater speed, simplicity and support. By reducing friction, enabling intelligent orchestration and improving continuity, Transamerica says Pearl cuts the typical transition timeline by more than 50%, and participants using Pearl do not incur any additional fees. "At Transamerica, we're enhancing customer experiences and actively fulfilling our commitment to helping people save and invest for their future selves," said Oriana Freidenberg, head of Customer Experience and Marketing at Transamerica. "Pearl makes it easier for our retirement plan participants to take action with clear guidance and timely support - while ensuring a Transamerica representative is readily available if a personal conversation is their preferred choice or the best next step." In a press release today, Transamerica noted that consolidating retirement assets is an important financial decision, but the process has traditionally been fragmented - often involving paperwork, multiple steps, and uncertainty about what comes next. Pearl streamlines this experience by creating a single, persistent participant space where AI guidance, relevant data, and human support come together in one place, rather than across disconnected channels, which the company says helps participants stay informed and move forward with confidence from start to finish. Participants are guided through key action steps like account verification, document collection and secure transfer of funds. Pearl helps ensure participants know what to do at each stage - reducing confusion, limiting rework and supporting a smoother path to completion. Pearl is designed with strong safeguards to help protect participant information, including encryption and robust security controls to support privacy and security throughout the experience. Together, these capabilities reflect a platform built to meet the regulatory expectations of the financial services industry. For this initiative, Transamerica teamed up with Zingly, an enterprise AI-powered customer experience platform. Zingly provides the secure, multimodal AI technology layer powering Pearl's intelligent experience, supporting Transamerica's continued focus on delivering innovative experiences for clients, plan sponsors and participants. On-demand human support. While Pearl streamlines the end-to-end experience, participants are not limited to a digital-only path. At any time, they can connect with a Transamerica representative for one-on-one support - whether they want reassurance, have questions or simply prefer speaking with a person. Human assistance is available during business hours. If a participant reaches out after hours, a representative responds the next business day to help ensure timely follow-up and continuity. Pearl remains available around the clock to answer questions, maintain progress and preserve context, ensuring participants can keep moving forward even outside business hours. Baltimore-based Transamerica is a leading provider of life insurance, retirement, and investment solutions for more than 10 million Americans. Veteran financial services industry journalist Brian Anderson joined 401(k) Specialist as Managing Editor in January 2019. He has led editorial content for a variety of well-known properties including Insurance Forums, Life Insurance Selling, National Underwriter Life & Health, and Senior Market Advisor. He has always maintained a focus on providing readers with timely, useful information intended to help them build their business. October 14, 2022 In "401(k) Practice" November 16, 2021 In "401(k) Products" August 30, 2023 In "401(k) Practice"

PR Newswire
Mar 16th, 2026
Transamerica launches AI assistant Pearl to cut retirement account consolidation time by over 50%

Transamerica has launched Pearl, an AI-powered virtual assistant that reduces retirement account consolidation time from weeks to days. The tool combines artificial intelligence, data and human support in a unified workflow to help participants transfer savings from other retirement accounts. Pearl provides step-by-step guidance through account verification, document collection and fund transfers, whilst maintaining security through encryption and privacy controls. Participants can access human representatives at any point during business hours, with Pearl available round the clock to maintain progress. Developed in partnership with Zingly, an enterprise AI customer experience platform, Pearl has reduced typical transition timelines by over 50%. The service is included at no additional cost to participants. Transamerica serves over 10 million Americans with life insurance, retirement and investment solutions.

Insurance Innovation Reporter
Mar 16th, 2026
Transamerica Launches AI Assistant for Retirement Rollovers

Transamerica launches AI assistant for retirement rollovers. The tool combines artificial intelligence and human support to speed consolidation of retirement accounts. Anthony R. O'Donnell // March 16, 2026 (Image source: Transamerica homepage.) Transamerica (Cedar Rapids, Iowa) has launched a virtual assistant designed to simplify the process of consolidating retirement accounts.The assistant, called Pearl, combines artificial intelligence, data and human support within a single workflow to help retirement plan participants move assets from external retirement accounts into Transamerica plans, according to a statement from the insurer. "At Transamerica, we are enhancing customer experiences while supporting people saving and investing for their future," comments Oriana Freidenberg, Head, Customer Experience and Marketing, Transamerica. "Pearl provides participants with guidance and timely support while ensuring a Transamerica representative is available when personal assistance is needed." The platform guides participants through steps such as account verification, document collection and transfer of funds. Transamerica says the system provides a single interface that combines automated guidance with access to representatives for assistance. The tool was developed with support from Zingly (Norris Canyon, Calif.), an enterprise artificial intelligence platform that provides the underlying technology for the assistant. Participants can access human assistance during business hours while the digital assistant remains available at all times to provide guidance and maintain workflow continuity. Transamerica says the tool can reduce the typical retirement account consolidation timeline by more than 50 percent. Transamerica provides life insurance, retirement and investment products to more than 10 million customers in the United States and is part of Aegon.

The Associated Press
Jan 28th, 2026
Empathy partners with Transamerica to offer loss support and legacy planning to 10M customers

Empathy, a technology company specialising in end-of-life planning and support, has announced a collaboration with Transamerica, one of America's largest life insurance providers serving over 10 million customers. The partnership will provide eligible Transamerica policyholders access to Empathy's Loss Support and LifeVault platforms. The collaboration offers families comprehensive guidance through bereavement, including funeral planning, claims management and estate organisation. Empathy currently serves more than 45 million families through partnerships with leading North American life insurers and handles one in five US life insurance claims beyond the payout. To support the expansion, Empathy has appointed Seth Miller as chief distribution officer. The company has raised $162 million from investors including Index Ventures and General Catalyst.