Judgment & Accountability
We bring senior leadership experience and take ownership of outcomes during critical moments.
Pilothouse Advisory is a founder-led executive consulting firm providing senior leadership during moments of complexity, transition, and change.
We work with CEOs, companies, and leadership teams who are navigating critical inflection points—whether it's a major technology investment, a digital transformation, organizational restructuring, or the adoption of AI and emerging technologies.
Our role is to step in as a trusted advisor and experienced leader, providing the judgment, clarity, and accountability needed to move forward with confidence.
We don't offer cookie-cutter solutions or buzzword-driven consulting. Instead, we bring decades of senior leadership experience across technology, strategy, and organizational change to help you navigate complexity and achieve meaningful outcomes.
The values that guide our work and define our relationships with clients.
We bring senior leadership experience and take ownership of outcomes during critical moments.
We navigate ambiguity and provide clear direction when organizations face difficult transitions.
We provide calm, confident guidance that inspires trust and drives meaningful change.
Pilothouse Advisory is led by a seasoned executive and Navy Veteran with over two decades of experience in technology leadership, digital transformation, and organizational change across global enterprises and high-growth organizations.
Our founder, Andrew Anderlonis, has served in C-suite and senior leadership roles, including President, Managing Director, COO, CTO and CTXO. He has led multi-million dollar transformation programs, advised company leadership on technology strategy, and guided organizations through critical transitions including mergers, restructurings, and digital modernization initiatives.
This depth of experience means we understand the pressures, complexities, and stakes involved in executive decision-making. We've been in the room, made the tough calls, and delivered results.
When you work with Pilothouse Advisory, you're not getting a junior consultant or a theoretical framework. You're getting a trusted partner with the judgment and experience to help you navigate your most critical challenges.
Engagements
Fractional CT(X)O
Providing executive technology leadership and driving transformation initiatives across multiple operating companies within a diversified property management and affordable housing portfolio.
Managing Director
Leading the technical and operational transformation of a newly acquired business, directing global and cross-functional teams, accelerating product innovation, and delivering more than 10x growth under a year.
Fractional CTO
Leading a major legacy modernization initiative, advising executive leadership, guiding platform re-architecture and modern software development practices, and recruiting key technical leaders.
Executive Technology Advisor
Advising executive leadership on technology strategy, building the technology function from the ground up, recruiting engineering leadership, and applying AI and emerging technologies to accelerate business growth.
Program Integration Lead
Leading a complex enterprise integration program across disparate operational and IT platforms, including the implementation of a new field service management system.
Executive AI Coach
Educating and coaching executive teams through AI readiness, governance, value mapping, strategic planning, and execution—building their internal capability to evaluate and implement high-ROI AI solutions.
Fractional CAIO
Providing executive AI leadership for a strategic growth initiative, encompassing AI education, opportunity mapping, solution planning, vendor evaluation, and statement-of-work development and execution.
Executive Technology Advisor
Advised the CEO and executive leadership on next-generation mobile application strategy, platform selection, feature prioritization, market reach, and the delivery of an intuitive user experience.
Executive Technology Advisor
Advised executive leadership and the board of directors on technology strategy and cost-effective investment decisions, identifying opportunities to streamline operations, improve productivity, and maximize resources.
Every engagement above started with a conversation about a decision that mattered. Yours can too.
Contact Pilothouse Advisory