Money Coach - Retirement Plan Specialist

Would you like to take ownership in a dynamic, high-growth business that truly walks the talk?

Oswald Companies seeks goal-driven professionals ready to take their career to the next level.

Job Title: Money Coach – Retirement Plan Specialist

Job Summary

As a Money Coach, you’ll serve as a key financial wellness resource for retirement plan participants, offering one-on-one guidance and group education to help them confidently plan for the future. You'll empower individuals to improve retirement readiness while uncovering broader financial needs and collaborating with senior financial advisors to ensure holistic support. This role blends coaching, travel, and referral management to support our mission of improving financial outcomes at scale.

Key Responsibilities

Participant Coaching & Education

• Conduct one-on-one and group coaching sessions focused on retirement readiness, budgeting, debt management, and investment basics.
• Provide guidance on plan features (e.g., contribution limits, employer match, Roth vs. Traditional).
• Help participants understand their retirement income gap and strategies to close it.

Needs Assessment & Opportunity Identification

• Use discovery conversations and financial wellness assessments to uncover broader financial planning needs (e.g., estate planning, tax strategies, insurance).
• Document and escalate qualified leads to senior financial advisors using a structured referral process.
• Refer at least $100k referral opportunities annually
• Participant in prospective meetings, representing the Money Coach Program
• Participant in annual client meetings to review Money Coach Program successes

Referral Management

• Collaborate with senior advisors to ensure smooth handoff and follow-through on referred opportunities.
• Track referral outcomes and maintain a feedback loop to improve lead quality and conversion.

Content & Resource Development

• Host webinars, workshops, and office hours to increase engagement and awareness.
• Collaborate with marketing to create any applicable materials.

Data & Reporting

• Maintain records of coaching sessions, participant progress, and referral metrics.
• Analyze trends to inform plan sponsors and internal teams about participant needs and engagement levels.

What You'll Need

• 3+ years of experience in financial coaching, retirement planning, or related client-facing roles.
• Understanding retirement plans and basic financial planning principles.
• Strong interpersonal skills and ability to build trust across diverse audiences.
• Organized, data-driven, and confident presentation to both individuals and groups.
• Willingness to travel 50–75%, mostly within Northeast Ohio and surrounding regions (15% overnight).
• Industry certifications a plus (e.g., CFP®, CRPC®, AFC®, or similar).

Who You Are

• A natural coach and educator who thrives on helping others make confident financial decisions.
• Passionate about improving retirement outcomes and promoting financial wellness.
• Self-starter who excels in fast-paced, client-focused environments.
• Collaborative and curious, with a desire to grow and evolve with the program.
• Skilled at balancing empathy with action, guiding conversations while driving results.

Success Metrics:

• Number of coaching sessions completed
• Participant satisfaction scores via surveys, feedback to Plan Sponsors
• Volume and quality of referrals to senior advisors
• Improvement in participant retirement readiness scores
• Engagement rates in educational programs

Travel Expectations:

50-75%, primarily in NEO or under 2hr distance; about 15% travel overnight locations (unless hired in central Ohio market).

Physical and Environmental Demands

This role involves typical duties performed in an office environment. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of the job. To request a disability-related reasonable accommodation to assist you in your job search, application, or interview process, please us at [email protected] to discuss your specific need.

• Physical Requirements: Primarily sedentary work involving sitting, typing, and handling office equipment. Occasional walking, standing, and lifting up to 10 pounds may be required.
• Manual Dexterity & Vision: Requires sufficient manual dexterity and visual acuity for computer use, data analysis, and document preparation.
• Work Environment: Standard indoor office setting with moderate noise levels and climate control.

Work Schedule & Hours 

Full-time hours: Core business hours of Monday through Friday from 8:00 AM to 5:00 PM and/or occasional weekend hours totaling 40 or more hours per week; no overtime payable.  (FLSA Status: Exempt) 

Who is Oswald?

Oswald is a 129-year-old company that creates a world of protection around the lives and businesses of our clients.

We are an independent, employee-owned company. So, essentially, you own your own success in a personally and financially rewarding opportunity.

Inclusivity is a priority. We foster an environment of collaboration and belonging where our Employee-Owners thrive on their unique path. Our diverse talent reflects the communities and clients we serve, while driving unmatched risk and insurance innovations.  

Our people-first culture and client service excellence have built our reputation of integrity, resourcefulness, and a relentless care for our clients and employees. Don’t believe us? Ask your friends, colleagues, and mentors about Oswald. There’s a reason Oswald has been named a Top Workplace for nine consecutive years.

What you’ll get...

At Oswald, you will have the opportunity to build a long-term career with unlimited growth potential. Aim high, work hard and we’ll help you achieve your goals. 

At Oswald, you will experience our caring work environment. We care about our Employee-Owners, we care about our customers, and we care about the world around us. Our caring personality comes to life in the form of volunteering in the community. We even give employees paid time off to volunteer with an organization of their choice.

At Oswald, you will achieve a work-life balance. We care about your physical and emotional well-being, so work-life balance is encouraged and practiced. We understand you have a life outside of work, and we want you to live it.

At Oswald, you will have access to a world-class Total Rewards package. We truly value our people, which shows in our compensation, benefits, and perks.

• In addition to competitive pay, we have designed a performance-based annual incentive program. All employees are eligible to earn a bonus by meeting performance objectives. 

• Comprehensive medical, dental and vision plans and numerous supplemental benefit offerings.

• Paid time off annually and a sabbatical at every 10-year service anniversary.

• Ownership in the company in the form of company stock (discretionary profit-sharing and 401(k) match contribution)

• Assistance with parking expenses, discount programs for area services/experiences, and financial support for professional development and licensure/designations

• Access to specialized leadership development programming designed to take your career to the next level.

• And so much more!

To learn more about Oswald, our culture and everything we have to offer, visit us on LinkedIn.

Oswald, a Unison Risk Advisors company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic.