Full-Time

Senior Training Manager

OneDigital

OneDigital

1,001-5,000 employees

Employee benefits, retirement, wealth, HR services

Compensation Overview

$70k - $90k/yr

+ Variable compensation + Commission + Annual bonus

No H1B Sponsorship

Chicago, IL, USA

In Person

Bachelor's

Category
People & HR (1)
Required Skills
Sales
Quality Assurance (QA)
Customer Service

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Requirements
  • Curriculum development, instructional design, and content creation are required.
  • Strong facilitation and presentation skills are required, with the ability to engage audiences of all sizes.
  • The ability to translate complex concepts into clear, engaging, and actionable learning experiences is required.
  • Strong interpersonal skills are required to build trust, credibility, and influence at all levels of the organization.
  • Excellent written, verbal, and presentation communication skills are required.
  • Proven leadership, coaching, and team development skills are required.
  • Strong organizational and project management skills are required, with the ability to manage multiple priorities and deadlines.
  • The candidate must be adaptable and able to thrive in a fast-paced, changing environment.
  • A high degree of professionalism, accountability, and attention to detail is required.
  • A bachelor's degree or equivalent experience is required.
  • At least one year of leadership or people management experience is required.
  • Demonstrated experience delivering presentations and facilitating training for audiences of varying sizes and organizational levels is required.
  • The candidate must be able to manage multiple training programs, projects, and competing priorities in a fast-paced environment.
  • The candidate must be eligible to work in the United States without work visa or residency sponsorship.
Responsibilities
  • Design, develop, and maintain comprehensive company training programs, onboarding, curricula, and learning content that align with business objectives, organizational priorities, and employee development needs.
  • Lead curriculum strategy and program design, ensuring training content remains current, effective, and aligned with company goals and industry best practice.
  • Partner with executive leadership, operations, quality assurance, sales, and human resources to identify performance gaps and implement learning solutions.
  • Utilize a variety of training methodologies, techniques, concepts, learning tools, and practices to ensure maximum effectiveness of training programs.
  • Monitor and measure the effectiveness of all training programs.
  • Lead, mentor, and develop a team of training managers and training leads.
  • Relay training effectiveness to OneDigital Advanced Health senior leadership.
Desired Qualifications
  • Experience in the Medicare or health insurance industry.
  • Experience leading training operations within a high-volume contact center or customer service environment.

OneDigital provides employee benefits and broader financial and HR solutions for employers. It began by offering online benefits for small and mid-sized employers, focusing on health, life, and disability insurance, and it grew by partnering with brokers to manage small-group clients and gain leverage with carriers. It now operates as a platform that combines insurance, retirement and wealth services, and HR consulting, expanding nationwide through the acquisition of more than 200 firms. Its goal is to help employers optimize benefits, financial well-being, and HR support at scale, backed by private ownership and large recapitalizations, including a 2025 majority investment by Stone Point Capital and CPP Investments.

Company Size

1,001-5,000

Company Stage

Acquired

Total Funding

$960M

Headquarters

Atlanta, Georgia

Founded

2000

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Simplify Jobs

Simplify's Take

What believers are saying

  • April 16, 2026 MP Wired for HR adds payroll and HCM technology.
  • February 2026 wealth deals added $1.73 billion AUA and Silicon Valley reach.
  • January 22, 2026 promotions of Bill Carew and Camry Blaising strengthen execution.

What critics are saying

  • April 2026 Salesforce breach exposed 28,414 client records, including Social Security numbers.
  • Class-action lawyers are targeting OneDigital Investment Advisors over the 2026 breach.
  • Acquisition-heavy growth strains integration; one failed control lapse can damage trust across all verticals.

What makes OneDigital unique

  • Stone Point and CPP bought OneDigital at over $7 billion on Sept. 19, 2025.
  • OneDigital bundles benefits, PEO, retirement, wealth, and HR into one platform.
  • Eleven PEO acquisitions since 2022 built localized scale across 18 offices.

Help us improve and share your feedback! Did you find this helpful?

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Disability Insurance

401(k) Retirement Plan

Paid Vacation

Paid Sick Leave

Performance Bonus

Professional Development Budget

Phone/Internet Stipend

Growth & Insights and Company News

Headcount

6 month growth

4%

1 year growth

4%

2 year growth

4%
TechRseries
Jul 23rd, 2026
OneDigital selects JIFFYAI to modernize investor onboarding and accelerate growth.

OneDigital selects JIFFYAI to modernize investor onboarding and accelerate growth. AI-powered Unified Onboarding solution will help OneDigital deliver a seamless, integrated onboarding experience aligned with its vision for holistic wealth management. JIFFYAI, a provider of AI-powered solutions for Wealth Management, announced that OneDigital, national insurance and financial services firm, has selected JIFFYAI's Unified Onboarding solution to transform its wealth management client onboarding experience. JIFFYAI's Unified Onboarding solution will empower OneDigital to onboard investors faster, improve conversion rates, lower onboarding costs, and scale efficiently without increasing dependence on operations and IT teams. As wealth firms grow, onboarding has increasingly become a critical differentiator. Yet many firms continue to struggle with fragmented systems, manual processes, lengthy account opening cycles, and disconnected client experiences that create operational bottlenecks and slow growth. OneDigital selected JIFFYAI's AI-powered Unified Onboarding solution to create a streamlined, digital-first onboarding journey that can support its integrated approach to wealth management and deliver a seamless experience for both clients and advisors. The solution will streamline complex multi-custodial onboarding processes, including integrations with custodial platforms such as Schwab and IWS, while synchronizing data with Salesforce to create a more connected and collaborative operating environment. By reducing operational complexity and eliminating data silos, the solution will empower OneDigital to onboard investors faster, improve conversion rates, lower onboarding costs, and scale efficiently without increasing dependence on operations and IT teams. "At OneDigital, we believe the future of wealth management lies in connecting every aspect of a client's financial life," said Chris Conyers, Vice President of Wealth Management Operations at OneDigital. "JIFFYAI gives us the ability to simplify complex onboarding journeys, create a more intuitive experience for clients and advisors, and establish greater consistency across the systems our teams rely on every day. This will help us operate more efficiently, collaborate better across our ecosystem, and build the operational foundation needed to support our continued growth." JIFFYAI's solution is uniquely differentiated by its ability to unify onboarding experiences across wealth, banking, and insurance businesses while leveraging data and Agentic AI to drive contextual decision-making. It comes pre-integrated with leading custodians, CRMs, and processing systems, enabling wealth firms to accelerate implementation and scale quickly. The onboarding solution unifies document digitization, workflow automation, compliance processes, account opening, funding, and data orchestration into a single intelligent experience. It also enables multi-product and multi-account onboarding, advisor transitions, and large-scale client migrations while integrating seamlessly with the firm's technology ecosystem. "Across the industry, firms are being held back by onboarding processes that were never designed for today's digital-first clients," said Babu Sivadasan, CEO of JIFFYAI. "Manual handoffs, fragmented systems, and compliance complexity are creating friction at the very moment firms should be building trust and deepening relationships. We're excited to work with OneDigital as they continue executing their growth vision. Our Unified Onboarding solution has helped leading financial institutions transform onboarding from an operational bottleneck into a strategic advantage, enabling them to deliver exceptional experiences at scale while creating capacity for future growth." This engagement further strengthens JIFFYAI's position as a trusted AI transformation partner for wealth management organizations seeking to modernize client journeys, unify operations, and build scalable foundations for long-term growth. [To share your insights with us, please write to [email protected]]

Yahoo Finance
Jul 16th, 2026
OneDigital Draws $1.8B Wealth Team from IBD Cetera

The eight-advisor team will bolster OneDigital’s presence in the Mid-Atlantic.

Captive Insurance Times
Jun 16th, 2026
Alliant appoints Searcy to employee benefits team

Alliant appoints Searcy to employee benefits team. Alliant Insurance Services appoints Kristin Searcy as senior vice president within its Employee Benefits Group, expanding the firm's strategic advisory capabilities across the Southeast. Searcy joins in May 2026, bringing more than two decades of experience advising executives and organisations on workforce strategy. Searcy's focus spans employee benefits, HR consulting, technology and process transformation, insurance strategy, employee engagement, and organisational development. A licensed benefit and property and casualty advisor, Searcy has guided organisations through challenges involving growth, culture, compliance, cost containment, and workforce experience. Searcy's background also includes experience in professional employer organisation (PEO) consulting. Searcy joins from OneDigital, where Searcy spent more than four years as a workforce strategy advisor and insurance broker. Earlier roles include an advisory position at HUB International and sales roles at Paycor and Paychex. Kevin Overbey, president of Alliant Employee Benefits, says: "Kristin is a rare blend of strategist, connector, and catalyst who provides transformative solutions to her clients amid a complex business landscape. Her diverse experience and deep connections will provide a powerful strategic advantage to clients from a range of industries." Searcy says: "I am here to help leaders create workplaces where people feel supported, energised, and aligned. My mission is to bring clarity to complexity, challenge outdated thinking, and design strategies that move organisations, and the people within them, forward." Alliant Insurance Services is among the largest insurance brokerage and consulting firms in the US. The firm's specialty operations include a captive insurance practice offering captive consulting and feasibility studies, domicile selection, captive formation and structuring, and reinsurance negotiation and placement.

PR Newswire
May 7th, 2026
OneDigital acquires South Carolina PEO Propel HR in first state market entry

Silva Capital Solutions has advised Propel HR on its acquisition by OneDigital PEO, a transaction that closed in January 2026. Silva Capital served as exclusive sell-side advisor in the deal. Founded in 1996 and based in Greenville, South Carolina, Propel HR is an IRS-certified professional employer organisation providing PEO, payroll and HR solutions to small and mid-sized employers across 49 states. The acquisition marks OneDigital's first PEO presence in South Carolina. Silva Capital Solutions, founded in 1998, specialises in mergers and acquisitions advisory within the PEO and HR outsourcing industries. The Atlanta-based firm has completed over 72 transactions and more than 2,000 advisory projects over 28 years. OneDigital, founded in 2000, is an insurance brokerage and HR solutions firm serving over 100,000 employers nationwide.

Citybiz
Apr 17th, 2026
OneDigital Acquires MP Wired for HR in Payroll and HR Tech Expansion

OneDigital has acquired Massachusetts-based MP Wired for HR, adding payroll and human capital management capabilities as the insurance brokerage and... Read More