Kumi Fernando-Calabrese, MBA, MSIT, CSM

Product & Platform Leader | Turning Ambiguity into Scalable Execution | AI & Digital Growth

Omaha, Nebraska, United States

About

I’m a product and platform executive who thrives in fast-moving, early and growth-stage environments, especially where innovation is moving faster than structure. I partner with founders and product teams to turn bold concepts into scalable, executable realities. My strength lies in translating ambiguity into clear priorities, aligned roadmaps, and operating rhythm; bringing just enough structure to accelerate progress without slowing innovation. My work often sits at the intersection of: • AI experimentation and product-market framing • Emerging platform strategy and real-world delivery • Growth ambition, disciplined execution and operational rigor I’ve led initiatives across SaaS, subscription, digital platforms, and AI-enabled products; bringing operating clarity to fast-moving teams while preserving the energy that fuels innovation. I’m often the connective layer between strategy and execution, aligning stakeholders, clarifying ownership, and turning emerging concepts into measurable progress. I’m energized by building, scaling, and bringing new products to life—especially when thoughtful structure enables innovation to grow. If you’re building something ambitious and need a steady partner to help it scale without losing speed, I’d welcome the conversation.

Experience

  • Product & Platform Leader at VIP Play, Inc.
    Jul 2025 - Present · 1 yr

    VIP Play, Inc. (OTCQB:VIPZ) is the corporate parent of VIP Play TN, a licensed sports wagering operator in the state of Tennessee. Partner with executive leadership to bring structure and operating discipline to a fast-moving product environment spanning AI initiatives, sportsbook platforms, and digital media products. • Introduce product discipline and prioritization frameworks in fast-moving innovation environment • Align AI experimentation with monetization strategy and regulatory guardrails • Coordinate cross-functional execution across engineering, data, marketing, and compliance • Stabilize release governance for compliance-sensitive initiatives • Translate emerging concepts into structured delivery roadmaps

  • Product & Platform Transformation Leader - Independant Consultant at RyLu Group, LLC
    Feb 2015 - Jul 2025 · 10 yrs 6 mos

    Partner to startup and mid-market, PE-backed organizations navigating growth, platform modernization, operating model evolution, and product maturity and discipline build outs. Engaged by executive teams to: • Build and formalize product operating models in engineering-led environments • Translate innovation and AI experimentation into structured roadmaps • Modernize digital and subscription platforms • Stabilize delivery in fast-moving, ambiguous environments • Align cross-functional execution across product, engineering, and business stakeholders Selected engagements include leadership roles at: • Lee Enterprises – Product & Platform Transformation • Tallo – Platform Rebuild & Operating Model Alignment • PrismHR – Post-Acquisition Product Integration • WorklogicEPS – SaaS Product Portfolio Leadership

  • Product & Program Leader (Consultant) at Lee Enterprises
    Mar 2024 - May 2025 · 1 yr 3 mos

    Lee Enterprises, a media company (NASDAQ: LEE) that publishes 77 daily newspapers in 26 states with digital subscription services. Leading a transformational initiative to modernize legacy systems across customer experience, subscription management, and payments. Known for bringing clarity to ambiguity—translating loosely defined ideas into actionable plans aligned with business outcomes. Building a product-oriented culture and framework to drive timely delivery, while uniting cross-functional teams around accountability, strategy, and execution.

  • Head of CAAP Implementation (Consultant) at Tallo
    Mar 2023 - May 2025 · 2 yrs 3 mos

    Tallo, a subsidiary of Stride Learning (NYSE: LRN), is an online platform geared towards learners. It provides various tools for students to explore career pathways, certifications, higher education by connecting them educators and employers with courses, scholarships, internships and employment opportunities. Oversee multiple work streams and projects to support platform transformation, including managing activities related capital budgeting, forecasting, contracts, internal and external labor allocations and reconciliation.

  • WorklogicEPS Implementation Leader (Consultant) at PrismHR
    Nov 2021 - Oct 2022 · 1 yr

    PrismHR, a leading software provider in the PEO/ASO industry. Acquired WorklogicEPS in November 2021. Participate and develop product strategies to reposition WorklogicEPS software to avoid market cannibalization. Integrate WorklogicEPS into PrismHR’s eco-system and back office processes. Serve as a product development lead and SME on all things related WorkLogicEPS.