VP of Technical Product Management $200,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
Enterprise software is drowning in complexity. Many products that power businesses today were built over a decade ago on outdated architectures, creating massive technical debt that slows innovation and inflates costs. Companies struggle to balance the need to modernize these legacy systems while ensuring business continuity, often resorting to incremental fixes rather than true transformation. AI presents a tremendous opportunity to break this cycle, but most organizations fail to integrate it meaningfully. Instead of using AI to fundamentally rethink how software is developed, maintained, and operated, they apply it as an afterthought—missing the chance to drive real efficiency and cost savings at scale.
Trilogy takes a different approach. As part of a larger M&A group, we acquire and transform software businesses by embedding AI and automation deep into their core processes. Rather than simply layering AI onto existing workflows, we rethink and rebuild from first principles, automating away inefficiencies and enabling lean, high-impact teams to deliver continuous improvement. Our focus is on making acquired products fundamentally better—simplifying legacy architectures, driving down operational costs, and accelerating the delivery of business value. This is an opportunity to lead that transformation across a diverse portfolio of enterprise and SMB products, making strategic technical decisions that shape the future of multiple software businesses.
This is not a product role centered on feature roadmaps, nor is it a pure engineering leadership role focused on managing teams. In this role, you will take full ownership of one or more acquired products. You will be responsible for ensuring product health, monitoring key performance metrics such as uptime and cost efficiency, and rapidly resolving escalations. Your role is to drive both short-term stability and long-term strategic improvements, ensuring that AI-driven automation is replacing manual effort at every level. Rather than simply firefighting, you will systematically modernize legacy architectures, make critical technical decisions, and drive execution through centralized engineering resources. You will work closely with business units and product managers, translating high-level strategic goals into clear, measurable technical outcomes that directly impact product performance and profitability.
As part of a high-caliber, results-driven team, you will operate in a fast-paced, asynchronous, and fully remote environment where success is measured by tangible outcomes. This is a role for technical leaders who thrive on high-stakes problem-solving and end-to-end ownership, not those who seek a narrowly defined technical focus. It will be an exciting fit for those who are energized by the challenge of modernizing complex software systems, integrating AI-driven automation, and making bold, strategic decisions that reshape entire products. If you are eager to drive transformation at scale and want to be at the forefront of AI-driven software evolution, we encourage you to apply.
What you will be doing
- Maintaining and demonstrating deep product expertise to guide strategic decisions
- Developing technical specifications that make sound and important technical decisions and prioritize simplicity, efficiency, and long-term viability
- Implementing generative AI technologies to automate and streamline engineering processes, aligning with the strategic vision of reducing manual labor
What you will NOT be doing
- Pure people management; your business and technical acumen will play critical roles in this position
- Wasting your time in meetings, committees, and administrative tasks; we have automated management overhead so you can focus on creating business value through hands-on work
- High-level strategies without implementation guidelines; your recommendations must be based on product-level insights
Key responsibilities
- Act as the CTO of a product, owning core competencies to modernize legacy systems, optimize costs, enhance AI-driven automation, and drive business value through seamless execution and strategic decision-making.
Candidate requirements
- Experience making important architecture and design decisions on software products that would be difficult or costly to undo, such as the application of architecture design patterns or significant open source technologies
- Experience making scope simplification decisions for a software product
- A deep understanding of the AWS ecosystem
- Experience using Generative AI to build product features and simplify work processes
Meet the hiring manager
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Pass Cognitive Aptitude Test.
Pass English Proficiency Test.
Prove Real-World Job & AI Skills.
Ace An Interview Or Two.
Accept Job Offer.
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