Startup Strategy and Turnaround Consultant

We are seeking a highly experienced startup strategist, business model architect, and turnaround specialist to work closely with the Founder as a fractional strategic advisor for A Way Out Pen Pals (AWOPP). This is not a generic consulting role. We need someone who can think deeply and creatively about a mission-driven, technology-enabled platform that connects incarcerated individuals with the outside world through pen pals and our proprietary Stay Connected IVR system. Proposals will only be considered if they include a detailed strategic outline and a fixed price. About AWOPP A Way Out Pen Pals is a modern, technology-forward platform that helps incarcerated individuals build meaningful connections with the outside world. We differentiate ourselves through strong social media marketing, advanced technology, and our Stay Connected IVR voicemail system, which allows incarcerated individuals to receive and manage voice messages and stay connected with friends and family in real time. We are building a broader connection ecosystem, not just a traditional pen-pal site. Current Challenge Our only current revenue model comes from incarcerated individuals who pay to post their profiles. We want to evolve this by increasing engagement from outside community members, creating a cycle where more outside users drive more incarcerated signups, exploring ways to shift some revenue toward outside users, and identifying new ethical, mission-aligned revenue streams for both sides. Historically, pen-pal platforms have not charged outside users to communicate with incarcerated individuals, so we need a strategist who can think differently and design a realistic path forward. Your Role You will act as a fractional Chief Strategy Officer and Revenue Architect. You will deeply analyze our platform, pricing, operations, and Stay Connected IVR system, clarify our core business model and value proposition, and propose multiple revenue models including subscriptions, memberships, premium features, partnerships, and mission-based funding. You will conduct a meaningful competitor analysis of platforms such as WriteAPrisoner, Meet-an-Inmate, and PrisonPenPals, identifying where we can outperform them and position AWOPP as the premium, modern leader in this space. You will also develop a clear growth and turnaround strategy for attracting more outside users, increasing incarcerated participation, strengthening our brand, leveraging the IVR system as a key differentiator, and structuring outreach with advocacy groups and nonprofits. You must deliver a structured roadmap with priorities, milestones, and measurable success indicators, and be willing to engage in ongoing strategy sessions with the Founder. What We Are Looking For Ideal candidates have experience with startups or turnaround situations, strong expertise in business model and revenue strategy, and experience with platforms or community-driven businesses. Bonus experience includes social impact, criminal justice reform, or subscription-based digital platforms. Proposal Requirements Your proposal must include a detailed strategic outline of your approach, your initial thoughts on potential revenue models, your perspective on shifting revenue toward outside users, a clear plan for analyzing our platform and competitors, and a fixed price for the full engagement. Proposals without a detailed outline and fixed price will not be considered. Additional Note on Long-Term Vision In addition to the business and revenue strategy above, we want a strategist who can help us work toward a broader vision of making AWOPP not only a leading pen-pal platform, but a platform that supports inmate rehabilitation and successful reentry, potentially through a future nonprofit arm that provides resources, education, and connections that reduce recidivism and better prepare individuals for life after incarceration. If you believe you can help reshape and grow A Way Out Pen Pals, we look forward to your proposal. Apply tot his job Apply To this Job