Practical Strategy for Energy, Technology, and Long-Term Growth
What We Do
Windward Ventures helps utilities, energy companies, and investors navigate growth, modernization, and strategic change with practical insight grounded in real operating experience.
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Strategic Planning
We help organizations align long-term vision with practical execution. From enterprise priorities and infrastructure planning to leadership alignment and organizational direction, we support strategies that create clarity, resilience, and measurable progress.
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Risk Strategy
We help leaders identify, assess, and manage operational, financial, regulatory, and technology-related risk. Our approach is designed to strengthen decision-making, protect enterprise value, and improve organizational readiness in a rapidly changing environment.
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Technical Strategy
We advise organizations on the modernization of critical technology and operational systems, including IT, OT, communications, automation, cybersecurity, and grid-facing infrastructure. The goal is to ensure technology investments support reliability, scalability, and long-term business objectives.
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M&A and Investment Advisory
We support strategic acquisitions, partnerships, and growth opportunities across the energy, engineering, renewable, and technology sectors. Our work includes opportunity sourcing, market insight, diligence support, strategic positioning, and transaction execution.
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Operational Improvement
We work with leadership teams to identify opportunities for stronger performance, better cross-functional alignment, and more effective use of capital and resources. This includes organizational efficiency, process improvement, and operating model refinement.
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Executive and Board Advisory
We provide trusted advisory support for CEOs, executive teams, and boards navigating complex decisions, transformation efforts, and long-range planning. Our perspective blends operational experience, financial discipline, and leadership insight.
Brett Olson is the Founder and Managing Director of Windward Ventures, a Nebraska-based strategic advisory and investment firm focused on energy, technology, and growth. He works with electric utilities, private equity firms, institutional investors, and technology companies to identify opportunities that create both financial value and long-term operational strength. With nearly two decades of leadership experience in public power, Brett brings a rare mix of utility operations, technology strategy, finance, and human-centered leadership. Before founding Windward Ventures, he served in senior leadership at Cornhusker Public Power District, overseeing key areas including AMI, GIS, IT, and SCADA while helping drive digital transformation, cross-functional collaboration, and system reliability. Through Windward Ventures, Brett leads strategic advisory engagements and supports transactions across the energy, engineering, renewable, and technology sectors. His work includes off-market deal sourcing, due diligence, growth strategy, capital optimization, and operational improvement for companies ranging from $10 million to $500 million in revenue. Brett is known for combining analytical rigor with a people-first mindset. He believes the best investments and business decisions are not just financially sound, but grounded in purpose, leadership, and long-term value creation. His broader industry contributions include work as a Research Designer for the U.S. Department of Energy’s National Energy Technology Laboratory, leadership in utility innovation, and founding Nebraska’s first IT/Cyber and Strategic Planning Community connecting 28 public power districts. He holds an MBA in Finance Management, a Master’s in Computer Information Systems Management, and is completing a Doctorate in Business Administration. At Windward Ventures, Brett’s mission is simple: help organizations grow stronger through thoughtful strategy, disciplined investment, and leadership that puts people at the center.