# Ross Stewart > Senior Product & Design Leader | Stabilizing Complex Systems, Scaling Execution, and Reducing Product Risk Location: San Francisco Bay Area, United States Profile: https://flows.cv/rossstewart I work at the intersection of product execution, design leadership, and operational clarity. I’m typically brought in when systems are complex, ownership is fragmented, or delivery has lost momentum. My role is to reframe the problem, align decision-making, and stabilize execution without unnecessary resets. Across cybersecurity, telecommunications, and large-scale enterprise environments, I’ve led teams through failed launches, regulatory constraints, and scaling transitions. The common thread is reducing product risk while improving speed, clarity, and trust. I started my career in design, but my work now centers on outcomes, not artifacts. Design is one of several levers I use to make complex systems understandable and executable. I’m most effective in environments where stakes are high, constraints are real, and progress depends on disciplined decisions rather than polish. ## Work Experience ### Founder & Product Lead @ PENTA Jan 2024 – Present | San Francisco Bay Area • Founded PENTA as an independent product and systems initiative focused on intelligence, risk assessment, and operational decision-making in regulated environments. • Apply lessons from enterprise cybersecurity, telecom, and industrial operations to explore how complex data, tooling, and workflows can be made executable under real-world constraints. • Work spans product framing, system architecture, and early validation rather than full-scale commercialization. • PENTA is exploratory and advisory in nature, and does not compete with employer IP or commercial product roadmaps. ### Senior Director, Product Design @ OPSWAT Jan 2019 – Jan 2024 | San Francisco Bay Area Cybersecurity platform serving governments, critical infrastructure, and regulated enterprises. • Joined at an early scale point to take ownership of core product and brand surfaces, inheriting distributed teams during a leadership transition and formalizing execution as the portfolio and customer base expanded. • Brought in to recover a product launch that failed to land, where roadmap execution and product boot sequence were misaligned with customer expectations. Reframed the problem as a system issue, reset decision ownership across product, engineering, and execs, and stabilized delivery without restarting the roadmap. • Enabled 0→1 delivery of six new products and sustained double-digit ARR growth by moving the organization from fragmented execution to a shared operating model. • Reduced downstream release risk by introducing a unified UI and interaction system, cutting usability-related defects by over half and shortening release cycles. • Partnered with engineering, security, and compliance leaders to align product surfaces with federal, accessibility, and InfoSec requirements, reducing enterprise deployment risk. • Built and led a distributed team of 12 across five countries, using local autonomy plus shared standards to increase delivery speed without sacrificing quality. ### Director, Digital Transformation @ Simplot Australia Pty Ltd Jan 2017 – Jan 2018 | Melbourne, VIC Global food and agriculture company serving large-scale food service and retail operations. • Led product and design initiatives focused on improving frontline sales effectiveness and operational clarity across a complex, brand-heavy organization. • Built and prototyped an iPad-based sales enablement tool used by field teams, significantly reducing prep and admin time and materially increasing time spent with customers. • Worked closely with sales, brand, and category teams to align digital tools with real-world food service workflows, grounding decisions in frontline constraints rather than marketing assumptions. • Contributed to early pilots integrating Simplot products into supermarket ecommerce platforms, bridging physical product distribution with emerging digital retail channels. ### Design Director @ Telstra Jan 2015 – Jan 2017 | Melbourne, VIC Australia’s largest telecommunications provider, serving millions of consumer customers. • Led UX and delivery for high-visibility consumer initiatives within a large, regulated telecom environment, working closely with product, brand, and compliance teams. • Owned design execution for the expansion of ecommerce from single-product to multi-product purchasing, enabling bundled offers and more complex buying paths. • Delivered internal broadband purchasing and city-wide Wi-Fi programs, balancing customer clarity, corporate brand alignment, and regulatory requirements under fixed launch timelines. ### Creative Director / Design Lead @ Publicis Sapient, Carat, Razorfish, Clemenger BBDO Jan 2006 – Jan 2014 • Led design and UX work across multiple agency environments, delivering under tight timelines, shifting briefs, and high client visibility. • Built early judgment in translating business intent into product and experience decisions, later applied in large-scale, regulated organizations. ### Interaction Designer @ Philips Jan 2004 – Jan 2006 ## Education ### Chief Product Officer Program Massachusetts Institute of Technology Jan 2023 – Jan 2025 ### La Trobe University ## Contact & Social - LinkedIn: https://www.linkedin.com/in/rossstewart - Website: https://rossstewart.me/ --- Source: https://flows.cv/rossstewart JSON Resume: https://flows.cv/rossstewart/resume.json Last updated: 2026-04-07