Principal Release Train Engineer (Global)

Principal Release Train Engineer Location: Worldwide (Remote/Hybrid) Reports to: CTO Principal, Release Train Engineer About CINC Systems CINC Systems is the largest provider of accounting and management software in the community association management industry and the innovator behind accounting and banking integration. Founded in 2005 by a banker as the industry’s first SaaS offering, CINC Systems now employs nearly 400 people and provides software and applications to more than 50,000 associations servicing over 5 million doors. In January of 2024, Hg Capital made a significant investment in CINC to accelerate the company’s growth trajectory and institute rapid product development. At CINC, innovation drives our growth, and our people sustain it. We are proud of our humble, accountable, and team-oriented culture, and we are committed to building products and a workplace that create long term value for our customers and our team. About the Role The Principal Release Train Engineer is a senior technical leader and coach responsible for designing and guiding the operating system of CINC Engineering. This person will lead the evolution of our release process, replacing traditional handoffs and approval gates with a continuous flow of value from idea to customer. This is not a process policing role. It is a systems leadership position for someone who understands how flow, feedback, and learning create performance. The Principal RTE will work across all product lines, guiding teams and leaders toward measurable improvement in deployment frequency, lead time, and reliability. Drawing on the work of thinkers such as Kent Beck, Don Reinertsen, Nicole Forsgren, Gene Kim, and Eli Goldratt, this person will help CINC build an organization where experimentation, trust, and data drive outcomes. Key Responsibilities · Lead the transformation of CINC’s release and delivery process from stage-gated to continuous flow, guided by Lean, DevOps, and flow principles · Coach engineering, product, and leadership teams on modern delivery practices including trunk-based development, small batch flow, test automation, and continuous delivery · Design and maintain the system of work for flow of value: visual management, cadence of planning, and alignment of product and platform initiatives · Define and measure delivery performance using DORA and flow metrics (deployment frequency, lead time, change failure rate, mean time to recovery, WIP, and flow efficiency) · Facilitate release planning and readiness reviews with a focus on improving the process, not just tracking the calendar · Partner with Platform & DevEx and Architecture teams to automate quality and compliance signals so approval becomes a function of system health, not meetings · Identify and address organizational bottlenecks using data, experimentation, and structured decision making · Work with Product and Engineering leaders to balance demand, capacity, and dependencies across the portfolio · Establish a culture of continuous improvement through retrospectives, postmortems, and system-level reflection · Ensure visibility and transparency of work in progress, risks, and dependencies through modern VSM tooling and dashboards · Coach teams in conflict resolution, encouraging constructive debate while maintaining respect, clarity, and shared accountability · Collaborate with the CTO and VP of Platform & DevEx to evolve governance models and delivery practices that align with the speed and safety goals of the organization Qualifications Experience and Background · 10+ years in software delivery or engineering leadership roles, including 5+ years coaching and leading delivery transformation across organizations of 100 or more people · Proven experience leading or transforming release processes toward continuous delivery in complex, multi-team software environments · Strong technical understanding of modern software engineering practices, including CI/CD pipelines, trunk-based development, automation, and DevOps principles · Deep familiarity with Lean flow concepts, constraints theory, and systems thinking · Experience using and interpreting delivery data (DORA, flow metrics, SLOs) to drive improvement and alignment · Background working with cloud-native and service-oriented architectures is a plus · Comfortable working across diverse technologies, from monoliths to microservices, with a focus on flow rather than specific tools · Experience with SQL Server or other enterprise database systems is advantageous Leadership and Skills · Highly disciplined thinker with the ability to analyze complex systems and simplify them into actionable patterns · Exceptional facilitator who can engage diplomatically but assertively across conflicting priorities · Skilled in using data and structured reasoning to resolve disputes and make progress without authority · Experienced in balancing the needs of speed, safety, and quality through continuous learning loops · Excellent communicator who can influence Principal leaders and inspire technical teams · Deeply collaborative, grounded in humility and respect for others’ expertise · Pragmatic and outcome-focused, avoiding bureaucracy while maintaining rigor Mindset and Values · Thinks in systems and constraints, always seeking leverage points that improve flow and learning · Believes in data over opinion and experiments over directives · Embraces conflict as a path to clarity when handled respectfully and transparently · Views process as a tool for alignment and improvement, not control · Embodies the principles of flow, feedback, and continuous learning · Leads with empathy, clarity, and technical credibility What Success Looks Like · The organization delivers value continuously with minimal friction between teams · Deployment frequency, lead time, and recovery time improve consistently quarter over quarter · Teams take ownership of their delivery flow and quality, using data to guide improvement · Release management evolves from a coordination activity to an automated, insight-driven system · Product and engineering leaders operate with greater clarity and trust, supported by reliable data and shared goals · The Principal RTE is recognized as a catalyst for alignment, performance, and sustainable speed across the organization CINC is an Equal Opportunity Employer of women, minorities, protected veterans and individuals with disabilities.