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In this episode of Time to Press Pause, host Ellen Williams speaks with Henry Poydar, founder and CEO of Steady, a predictive coordination platform that grew out of his earlier venture, Status Hero. Henry describes two pivotal moments when he paused to reconsider his next steps. After co-founding Bantam CRM and joining Constant Contact post-acquisition, he spent three years working on a major systems integration project—a process he likens to open-heart surgery. Longing to return to hands-on product development, he created Status Hero, a tool that addressed the challenges of large teams trying to stay aligned asynchronously. Eventually, he built Status Hero to a seven-figure ARR before realizing he needed additional capital to scale beyond his solo efforts. Choosing investors who shared his commitment to sustainable growth allowed him to assemble an elite distributed team and rebrand as Steady, expanding the product’s capacity to serve entire organizations.

Throughout the conversation, Henry highlights how his technical background fueled fast, iterative development and let him adapt Status Hero to user feedback almost instantly. He also underscores the value of maintaining strong networks, crediting connections from Constant Contact and elsewhere with helping him raise the kind of funding that aligns with his vision. Finally, he emphasizes the importance of transparent communication and context-sharing so that everyone on a team understands the “why” behind decisions. According to Henry, leaders should be deliberate about taking time to reflect, ensure the entire organization remains curious and informed, and continuously reinforce the mission and values that guide the work.