Raissa Silva
Raissa Silva is the CEO and Founder of Outsmart Your Toxic Boss™, a workplace culture and organizational strategy brand operating at the intersection of humor, systems thinking, and corporate transformation. She is also the creator of The Corporate Menace™, a satirical card game that turns corporate dysfunction into an interactive experience, helping professionals recognize toxic workplace archetypes and reframe challenging dynamics through humor, strategy, and play. Her work spans keynote speaking, consulting, workshops, and content creation designed to shift how individuals and organizations understand and respond to workplace toxicity.
Raissa spent five years working in HR and talent acquisition, where she developed a deep understanding of how organizations operate from a people and systems perspective. Through her work in operations and recruiting, she gained firsthand insight into hiring structures, workforce strategy, and the internal mechanics that shape corporate culture. Like many professionals, she also encountered a toxic leadership experience that ultimately became the catalyst for her current work, transforming that experience into a broader mission focused on awareness, empowerment, and systemic change.
Today, Raissa blends her corporate operations background with creative strategy, humor, and education to build tools that help people navigate workplace challenges in new ways. The Corporate Menace™ was born from the idea of turning corporate politics, often described as a “game,” into an actual game that allows people to safely explore, laugh at, and understand toxic archetypes without fear. The game also serves as a practical tool for organizations, offering a new lens into recognizing and addressing dysfunctional behavior. In her current pre-launch phase, Raissa works closely with organizational psychologists, employment law attorneys, CHROs, and executives while managing marketing campaigns, digital content creation, product development, and research in organizational design. She is actively building toward a Kickstarter launch in June 2026, with a goal of reaching 10,000 waitlist subscribers before release.
• Simmons University - BA, Public Health
• Employee of the Quarter awards
• Leadership workshop nominations
• National Sales Competition
• Planned legal fund for employees facing workplace issues (percentage of game sales to provide employment law attorney access)
• Dwell with Dignity
What do you attribute your success to?
I would attribute my success to my ability to help others recognize that they are not alone in experiencing workplace abuse and to empower them to reclaim their agency. One of my most meaningful professional achievements has been navigating and outsmarting a toxic leadership situation in a way that I can confidently and legally stand behind, transforming a difficult experience into growth and insight. This journey reinforced my belief that individuals are never truly powerless in their careers, and that with resilience, self-trust, and the support of a strong network, it is possible to move beyond fear, challenge unhealthy systems, and intentionally design healthier, more accountable workplaces where people can thrive.
What advice would you give to young women entering your industry?
If you're starting your own business, I would say focus on a problem that you cannot stop thinking about. Something that literally lights a fire under your bum. And it doesn't feel like work, it feels like play. Whether that be you really love cosmetics and you love the different kind of pigments and the sparkles that come in different eyeshadows and you're obsessed, or if that means that you are super fascinated by the chemistry in gasoline, or you're really fascinated by space and you want to do something that helps push astronomy forward. Whatever it is that lights you up inside and brings you joy, that is something that you should probably consider turning into a business, because that's what's going to keep driving you forward on the days that you're not really getting much external traction. When it comes to advice at work, the reality is most people are kind professionals. There are a small few that are bad apples. That doesn't mean that you shouldn't be vigilant. You should be. Be vigilant. Document things. Realize that documentation isn't to get back at one individual person. That when you come across a toxic boss, outsmarting them doesn't mean that you're trying to get revenge on that particular individual. Documentation is power. Strategy is survival. You don't have to react emotionally to something you can outthink structurally.
What are the biggest challenges or opportunities in your field right now?
Toxicity in the workplace has been so deeply normalized that many people no longer question it, accepting dysfunction as a condition of employment rather than a failure of leadership. That normalization is reinforced by a clear power imbalance: employees are encouraged to speak up, yet rarely protected when they do, leaving accountability optional for those at the top and risky for everyone else. Compounding this is a widespread lack of documentation and strategy, where individuals with valid experiences still lose because they lack the structural tools to defend themselves. Translating these realities into The Corporate Menace introduces another layer of complexity—building something that is both engaging and honest without diminishing the seriousness of the issue. At the same time, I’m tasked with educating a market while earning trust from people I’m asking to rethink deeply ingrained beliefs about work and leadership. And through it all, fundraising remains a proving ground—where visibility must be earned, not assumed, and resonance matters more than reach.
What values are most important to you in your work and personal life?
The values most important to me in both my work and personal life center on resilience, self-advocacy, and empowerment. I believe deeply in helping individuals build the confidence and tools to navigate workplace challenges, resolve conflict constructively, and recover from workplace trauma in a healthy and sustainable way. I also value innovative and human-centered approaches to healing, including the use of games as therapeutic tools and humor as a meaningful coping mechanism. Equally important to me is fostering strong, supportive communities where survivors of workplace abuse feel seen, believed, and connected. Ultimately, my work is guided by a commitment to transforming difficult professional experiences into growth, clarity, and long-term resilience.
Locations
Outsmart Your Toxic Boss™
Chicago, IL 60647