Senior Onboarding Specialist

About the role

We are adding a Senior Onboarding Specialist to our Customer Success team. Building on a strong foundation in client enablement, the Senior Onboarding Specialist takes ownership of the most complex and high-value client onboarding engagements, while also playing a leadership role in shaping the onboarding function itself.

Responsibilities

• Own the end-to-end onboarding experience for complex, high-priority, or enterprise-level advisor clients, from kickoff through full platform activation.
• Design, deliver, and continuously refine structured onboarding programs, training curricula, and client-facing resources.
• Act as a senior platform subject matter expert, providing in-depth guidance on RPAG features, workflows, and best practices.
• Develop a deep understanding of each client’s business model and goals, and tailor the onboarding experience accordingly to drive meaningful adoption.
• Monitor and analyze client adoption and engagement data; proactively identify risk and develop mitigation strategies to ensure successful platform utilization.
• Mentor and support junior Onboarding Specialists, serving as a resource for escalated questions and providing coaching on best practices.
• Lead the development and maintenance of onboarding playbooks, scalable training materials, and knowledge base content.
• Collaborate cross-functionally with Sales, Product, Marketing, and Customer Support to align on client messaging, drive feedback loops, and improve the overall client experience.
• Represent the onboarding team in product roadmap discussions, contributing the client perspective to feature prioritization.
• Maintain accurate and detailed records of client engagement and onboarding progress in Salesforce.
• Travel to client sites, company events, and industry conferences to deliver training and deepen relationships (travel expected approximately 4–6 weeks per year).

Qualifications & Experience

• Bachelor’s degree and 5+ years of experience in client onboarding, customer success, training, or a related client-facing discipline, preferably in financial services, fintech, or SaaS.
• Demonstrated track record of managing complex, high-value client relationships and delivering measurable adoption outcomes.
• Experience with adult learning principles, instructional design, or formal training program development.
• Deep familiarity with the retirement planning or wealth management industry strongly preferred.
• Exceptional presentation, facilitation, and communication skills; able to engage and influence audiences ranging from end users to C-suite stakeholders.
• Experience working cross-functionally and influencing without direct authority.
• Proficient in Salesforce or comparable CRM; experience with LMS or digital training platforms is a plus.
• Strong analytical mindset with the ability to interpret adoption data and translate insights into action.
• Experience mentoring or informally leading peers; prior team lead or senior individual contributor experience preferred.
• Able to thrive in a fast-paced, dynamic environment and manage multiple priorities effectively.
• Comfortable navigating ambiguity.
• Entrepreneurial mindset to bring best practice ideas to the team.

Company Background

We have a comprehensive and competitive benefits package at Great Gray. Some of the highlights are:

• Be an integral part of a high-growth organization!
• Competitive compensation package
• Group medical, dental and vision insurance
• Employer-paid life and disability insurance
• Annual well-being stipend
• Eligible employees may also contribute to a 401(k) plan with an advantageous employer contribution model, upholding our mission to support our employees in retirement

Equal Employment Opportunity Policy

Great Gray Group, LLC is an Equal Opportunity Employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, disability status or other non-merit factor.