The People Group is a fractional talent and support business focused on connecting exceptional professionals with growing founders and leadership teams. We pride ourselves on quality, consistency, and long term partnerships. We believe that when our contractors are treated with respect, clarity, and fairness, that standard naturally carries through to the clients they support. Clear expectations, open communication, and mutual accountability are central to how we work. We are currently seeking a highly skilled and tech savvy Executive Assistant with strong AI and automation experience to join our talent pool on a freelance basis. In this role, you will support founders and senior leaders by managing operations, optimizing workflows, and leveraging AI tools to drive efficiency and productivity. This is a fully remote, fractional role supporting clients across multiple time zones, ideal for someone who is proactive, detail oriented, and comfortable working independently in a fast paced environment. Responsibilities - Manage calendars, schedule meetings and appointments for clients - Coordinate travel arrangements and accommodations - Prepare and edit documents, reports, and presentations - Handle phone calls, emails, and other correspondence - Organize and maintain files, records, and databases - Assist in the preparation of meeting agendas and take minutes - Collaborate with other team members to ensure efficient workflow - Arrange and coordinate events and conferences - Perform ad-hoc administrative tasks as needed - Respond to and manage client requests, including ad hoc tasks, with professionalism and attention to detail

The People Group is a fractional talent and support business focused on connecting exceptional professionals with growing founders and leadership teams. We pride ourselves on quality, consistency, and long term partnerships. We believe that when our contractors are treated with respect, clarity, and fairness, that standard naturally carries through to the clients they support. Clear expectations, open communication, and mutual accountability are central to how we work. We are currently seeking a highly skilled and tech savvy Executive Assistant with strong AI and automation experience to join our talent pool on a freelance basis. In this role, you will support founders and senior leaders by managing operations, optimizing workflows, and leveraging AI tools to drive efficiency and productivity. This is a fully remote, fractional role supporting clients across multiple time zones, ideal for someone who is proactive, detail oriented, and comfortable working independently in a fast paced environment. Responsibilities - Manage calendars, schedule meetings and appointments for clients - Coordinate travel arrangements and accommodations - Prepare and edit documents, reports, and presentations - Handle phone calls, emails, and other correspondence - Organize and maintain files, records, and databases - Assist in the preparation of meeting agendas and take minutes - Collaborate with other team members to ensure efficient workflow - Arrange and coordinate events and conferences - Perform ad-hoc administrative tasks as needed - Respond to and manage client requests, including ad hoc tasks, with professionalism and attention to detail

Role Description The People Group is currently seeking a highly skilled and tech-savvy Executive Assistant with strong AI and automation experience to join our talent pool on a freelance basis. In this role, you will support founders and senior leaders by managing operations, optimizing workflows, and leveraging AI tools to drive efficiency and productivity. This is a fully remote, fractional role supporting clients across multiple time zones, ideal for someone who is proactive, detail-oriented, and comfortable working independently in a fast-paced environment. Responsibilities - Manage calendars, schedule meetings and appointments for clients - Coordinate travel arrangements and accommodations - Prepare and edit documents, reports, and presentations - Handle phone calls, emails, and other correspondence - Organize and maintain files, records, and databases - Assist in the preparation of meeting agendas and take minutes - Collaborate with other team members to ensure efficient workflow - Arrange and coordinate events and conferences - Perform ad-hoc administrative tasks as needed - Respond to and manage client requests, including ad hoc tasks, with professionalism and attention to detail - Experience using AI tools like ChatGPT, Claude, Gemini - Prompt writing and optimization - Ability to automate workflows (Zapier, Make, etc.) - Experience using AI for: - Research - Summarization - Email Drafting - Task Management Qualifications - Experience working in a fractional, freelance, or contract-based role - Exceptional organizational and time-management skills - Excellent communication and interpersonal abilities - Proficient in MS Office and Google Suite - Ability to multitask and prioritize tasks effectively - Strong attention to detail and accuracy - High degree of professionalism and confidentiality - Ability to work independently and remotely - Flexible schedule and availability - Demonstrated experience supporting multiple executives or clients simultaneously - Experience with project management tools - Familiarity with video conferencing and online collaboration tools - Knowledge of office management systems and procedures - Experience working with HNW individuals preferable but not essential - Experience working with Family Offices preferable but not essential - Experience working with Business Leaders preferable but not essential - Flexible with occasionally meeting clients in person if requested - Knowledgeable about emerging AI software, tools, models, and methodologies that challenge the conventional approach to executive assistance Benefits You will be working as a contractor under The People Group company name, therefore you are not a direct employee and only work as a contractor for our business. The benefit of this structure means all of our clients sign contracts directly with The People Group and not you as the Contractor, therefore you are protected as a remote contractor as The People Group takes care of the client service side of the function.

Title: Account Executive, Employee Benefits Location: Remote - Ohio Job Description: time type Full time job requisition id JR104648 The Account Executive interacts with clients on a day-to-day basis while developing and maintaining relationships with both client and carrier representatives to develop and execute on the client’s benefit strategy. The Account Executive will research, analyze, and evaluate medical, life, disability and other benefit plans and serve as the benefit expert to clients. The Account Executive is the primary point of contact for clients and will have indirect supervision of team members, review work for accuracy and delegate work and projects to other members of the team to ensure client deliverables are timely and accurate. The Account Executive is responsible for revenue growth – client expansion – on their personal book of business and assisting producers and team with prospecting new clients, including proposal development. The qualified candidate must have strong knowledge across the spectrum of employer-sponsored health & welfare related plans, including federal and state regulations that impact these plans. Your Impact: - Serve as a subject matter expert on Health & Welfare benefits, including medical, dental, vision, life, disability, and voluntary products - Manage and grow a book of business exceeding $1M in revenue - Build and maintain strong, reference‑ready relationships with clients, prospects, and carrier partners - Proactively advise clients on industry trends, regulatory updates, and strategic solutions to address evolving needs - Lead RFPs, renewals, and open enrollment processes, including carrier negotiations and client recommendations - Apply underwriting fundamentals to explain funding options, rate impacts, and cost drivers - Project manage the book of business, ensuring timely deliverables, accurate system updates (e.g., BenefitPoint, AMS), and full regulatory compliance - Review work product, provide feedback, and mentor junior team members while leveraging internal tools and resources to maximize efficiency Successful Candidates Will Have: - BA/BS preferred - Life, Accident and Health Insurance License required - 5+ years of health & welfare experience, meets, or exceeds, core practice competency-based skills - Client-facing experience in the employee benefit industry - Technical knowledge of benefits administration, HealthCare Reform, industry trends, carrier products and services Physical Demands and Work Environment - While performing the duties of this job, the employee is required to regularly sit, hear, and reach with hands and arms. The employee is occasionally required to stand and walk. The employee must regularly lift and/or move up to 10 pounds. Specific vision abilities required by this job include close vision and the ability to adjust focus - The work environment characteristics described are representative of those employees performing the essential functions of this job. The noise level in the work environment is usually moderate to loud. Occasional travel Pay Range: $51,800 - $85,000 Annual The pay range provided above is made in good faith and based on our lowest and highest annual salary or hourly rate paid for the role and takes into account years of experience required, geography, and/or budget for this role. Risk Strategies is an equal opportunity workplace and is committed to ensuring equal employment opportunity without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, Veteran status, or other legally protected characteristics. Learn more about working at Risk Strategies by visiting our careers page: www.risk-strategies.com/careers. Personal information submitted by California applicants in response to a job posting is subject to Risk Strategies' California Job Applicant Privacy Notice.