Principal Software Engineer, Trilogy (Remote) - $200,000/year USD
In the world of enterprise software, complexity reigns supreme. Many of today's business-critical products are shackled by outdated architectures and technical debt, stifling innovation and inflating costs. Companies face the daunting task of modernizing these legacy systems while maintaining business continuity, often opting for piecemeal fixes over genuine transformation. AI holds the promise of breaking this cycle, yet many organizations fail to harness its true potential, relegating it to an afterthought rather than a catalyst for efficiency and cost savings.
Trilogy stands apart. As part of a larger M&A group, we specialize in acquiring and revitalizing software businesses by embedding AI and automation at their core. Rather than merely layering AI onto existing workflows, we rethink and rebuild from the ground up, eliminating inefficiencies and empowering lean, high-impact teams to drive continuous improvement. Our mission is to fundamentally enhance acquired products—simplifying legacy architectures, reducing operational costs, and accelerating business value delivery. This role offers the chance to lead this 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 role focused on product feature roadmaps, nor is it solely about engineering leadership. You'll take full ownership of one or more acquired products, ensuring their health by monitoring key performance indicators like uptime and cost efficiency, and swiftly addressing escalations. Your mission is to drive both short-term stability and long-term strategic enhancements, ensuring AI-driven automation replaces manual efforts at every level. Instead of firefighting, you'll systematically modernize legacy architectures, make critical technical decisions, and drive execution through centralized engineering resources. Collaborating closely with business units and product managers, you'll translate high-level strategic goals into measurable technical outcomes that directly impact product performance and profitability.
As part of a top-tier, results-oriented team, you'll operate in a fast-paced, asynchronous, and fully remote environment where success is measured by tangible outcomes. This role is tailored for technical leaders who excel in high-stakes problem-solving and end-to-end ownership, not those seeking a narrowly defined technical focus. It's an exciting opportunity for individuals energized by the challenge of modernizing complex software systems, integrating AI-driven automation, and making bold, strategic decisions that reshape entire products. If you're eager to drive large-scale transformation and be at the forefront of AI-driven software evolution, we invite you to apply.
What You Will Be Doing
• Maintaining deep product expertise to guide strategic decisions
• Crafting technical specifications that prioritize simplicity, efficiency, and long-term viability
• Implementing generative AI technologies to automate engineering processes, aligning with the strategic vision of reducing manual labor
What You Won’t Be Doing
• Managing people; your business and technical acumen will be crucial
• Spending time in meetings, committees, and administrative tasks; automated management overhead allows you to focus on creating business value through hands-on work
• Developing high-level strategies without implementation guidelines; your recommendations will be grounded in product-level insights
Principal Software Engineer Key Responsibilities
• Serve 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.
Basic Requirements
• Experience making critical architecture and design decisions on software products that are difficult or costly to undo, such as applying architecture design patterns or significant open source technologies
• Experience in scope simplification decisions for a software product
• Deep understanding of the AWS ecosystem
• Experience using Generative AI to build product features and simplify work processes
About Trilogy
Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-3293-US-NewYork-PrincipalSoftw-1.002
Apply Now
Apply Now
Trilogy stands apart. As part of a larger M&A group, we specialize in acquiring and revitalizing software businesses by embedding AI and automation at their core. Rather than merely layering AI onto existing workflows, we rethink and rebuild from the ground up, eliminating inefficiencies and empowering lean, high-impact teams to drive continuous improvement. Our mission is to fundamentally enhance acquired products—simplifying legacy architectures, reducing operational costs, and accelerating business value delivery. This role offers the chance to lead this 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 role focused on product feature roadmaps, nor is it solely about engineering leadership. You'll take full ownership of one or more acquired products, ensuring their health by monitoring key performance indicators like uptime and cost efficiency, and swiftly addressing escalations. Your mission is to drive both short-term stability and long-term strategic enhancements, ensuring AI-driven automation replaces manual efforts at every level. Instead of firefighting, you'll systematically modernize legacy architectures, make critical technical decisions, and drive execution through centralized engineering resources. Collaborating closely with business units and product managers, you'll translate high-level strategic goals into measurable technical outcomes that directly impact product performance and profitability.
As part of a top-tier, results-oriented team, you'll operate in a fast-paced, asynchronous, and fully remote environment where success is measured by tangible outcomes. This role is tailored for technical leaders who excel in high-stakes problem-solving and end-to-end ownership, not those seeking a narrowly defined technical focus. It's an exciting opportunity for individuals energized by the challenge of modernizing complex software systems, integrating AI-driven automation, and making bold, strategic decisions that reshape entire products. If you're eager to drive large-scale transformation and be at the forefront of AI-driven software evolution, we invite you to apply.
What You Will Be Doing
• Maintaining deep product expertise to guide strategic decisions
• Crafting technical specifications that prioritize simplicity, efficiency, and long-term viability
• Implementing generative AI technologies to automate engineering processes, aligning with the strategic vision of reducing manual labor
What You Won’t Be Doing
• Managing people; your business and technical acumen will be crucial
• Spending time in meetings, committees, and administrative tasks; automated management overhead allows you to focus on creating business value through hands-on work
• Developing high-level strategies without implementation guidelines; your recommendations will be grounded in product-level insights
Principal Software Engineer Key Responsibilities
• Serve 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.
Basic Requirements
• Experience making critical architecture and design decisions on software products that are difficult or costly to undo, such as applying architecture design patterns or significant open source technologies
• Experience in scope simplification decisions for a software product
• Deep understanding of the AWS ecosystem
• Experience using Generative AI to build product features and simplify work processes
About Trilogy
Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-3293-US-NewYork-PrincipalSoftw-1.002
Apply Now
Apply Now