Product Executive
Michael Caldwell
I'm a product leader with a strong track record of building high-performing teams and shipping products that scale.I've helped grow startups and public companies alike, driving innovation, scaling operations, and mentoring cross-functional teammates across product, engineering, design, marketing, and ops.
FOUNDER & CEO
SUCCESSFUL FOUNDER
I founded and scaled one of the first transactional entertainment marketplaces, growing it from the ground up to 40 employees and over $4M in ARR.Along the way, I built a loyal, high-performing team with exceptional retention from founding through acquisition. I led the successful acquisition negotiations with The Knot Worldwide.
HEAD OF PRODUCT / INTERIM CTO
PRODUCT & ENGINEERING LEADER
Case Study: Driving a Turnaround for a 5M+ User Social PlatformI joined a venture-funded startup as Head of Product and was later elevated to Interim CTO. The company’s flagship platform had gone dormant, but I helped bring it back to life, resetting the product vision, rallying a cross-functional team, and driving execution across design, product, and engineering.As Interim CTO, I aligned our tech strategy with business priorities and re-established a culture of velocity and collaboration.
OPERATIONAL INNOVATOR
AI FIRST THINKER
Case Study: Using AI to Drive Product InnovationAt a venture-backed startup, I championed and led the integration of AI-powered features across our platform. This included automatic profile bio generation, intelligent image optimization, and voice-to-text feedback summaries for post-lesson reviews.I partnered closely with engineering to bring these ideas to life, and grounded them in real user needs -not novelty.
MARKETPLACE VETERAN
INDUSTRY LEADER
I bring an entrepreneurial, growth-minded approach to every product role, shaped by 20+ years of platform experience and the journey of founding and scaling a company.I believe in building team cultures where impact, ownership, and continuous improvement are core values. Every team member should know their work matters. Every day should move the needle.I'm always excited to connect with founders, product leaders, and mission-driven teams building what’s next.
