Entrepreneurship & Small Business Advisor

The Workaround Collective · Remote (USA) · Remote · Part-time

REQ-2026-5272 · Hiring manager: Connie L., Founder

Job Title: Entrepreneurship & Small Business Advisor (Remote, 1-on-1) The Mission Not every career comeback means going back to a traditional job — for many job seekers, the path forward is building something of their own. We are looking for a seasoned Entrepreneurship & Small Business Advisor to help job seekers explore, launch, and grow their own businesses. You will provide remote, personalized guidance to help clients turn an idea into an actionable plan, avoid common first-time pitfalls, and build the confidence to become their own boss during a season of change and reinvention. What You Will Do * Provide 1-on-1 remote sessions to help job seekers validate business ideas, define their target market, and map out a realistic launch plan. * Guide clients through the fundamentals of starting a business — business models, pricing, budgeting, legal/setup basics, and landing first customers. * Help clients build a personal brand and marketing approach that attracts their first clients or sales. * Share practical, real-world lessons from launching and running successful ventures, including how to navigate setbacks. * Coach clients on setting realistic milestones and staying accountable as they build. * Contribute digital content 1x a week to our in-platform digital library. * Build your brand and drive bookings by offering free small group discussions or webinars in our in-app virtual rooms. Who You Are * Proven Founder: You have a proven track record of successfully launching and growing one or more businesses. * Practical Strategist: You can break the overwhelming process of starting a business into clear, achievable steps for beginners. * Empathetic Guide: You understand the financial and emotional pressures of unemployment and meet clients with encouragement and honesty. * Digital Communicator: You excel at building trust and delivering impactful, actionable advice over video software. * Versatile Advisor: You can tailor your guidance to a range of business types, industries, and budgets. Why Join Us * Direct Impact: You will help job seekers create their own opportunities and take control of their futures. * Total Flexibility: Work from home anywhere in the US * You set your hours and your booking rate * Create content and teach job seekers about a topic that you are passionate and knowledgeable in * Purpose-Driven and Mission-Driven Culture: Join a team that truly values the meaning and power of human community and connection. About The Workaround Collective The Workaround Collective is a newly formed 501(c)(3) tax-exempt nonprofit headquartered in Bryan, TX. Our mission is to leverage the power of human connection to support job seekers through the demands and challenges of their job search. We connect them to educational, wellness, and career-support experts, mentors, peers, and educational and financial resources through our in-house digital library and (future-planned) grants-assistance programs. Because we are newly launched, we are intentionally starting small as we ramp up. This role is a great fit if you want a fun, creative, and inspiring place to work — fully remote, with flexible hours and the freedom to build a meaningful side hustle while helping to build a community that cares. The minimum hours required to start is to be available at least 4 hours per month for 1x1 virtual sessions with job seekers. The long term vision is for the Workaround Collective to transition our experts to direct staff as the organization expands and funding grows. If you want to make a real difference in the lives of job seekers and to grow and contribute to the vision and future of the organization, we'd love for you to apply to join our team!