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}  ($100 USD/hour)

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 Many products that power businesses today were built over a decade ago on outdated architectures, creating massive technical debt that slows innovation and inflates costs.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.