Role Description Coursedog is looking for a dynamic, AI-forward product operations leader to be the operational backbone of our Product & Engineering organization. As Coursedog’s Director, Product & Engineering Operations, you’ll serve as the connective tissue of our Product & Engineering organization, shaping how we build, deliver, and improve at scale. Reporting to the SVP of Operations, you’ll own the systems, processes, data, and governance frameworks that enable teams to move with speed, clarity, and confidence. This is a high-impact, cross-functional role that blends strategy with hands-on execution. You’ll design and operationalize an AI-augmented PDLC, own and evolve core systems like Jira and our product tech stack, and build the reporting and feedback loops that drive better decisions across the business. This role offers a competitive base salary ranging from $150,000-$165,000, depending on experience, with total on-target earnings (OTE) of $180,000-$210,000 when goals are met. What You'll Own - AI-Driven Product Development Lifecycle (PDLC) - Own the end-to-end PDLC framework from discovery and prioritization through delivery, launch, and post-launch evaluation by embedding AI tooling to improve speed, quality, and consistency. - Identify and deploy AI-assisted workflows for spec generation, roadmap synthesis, release note drafting, retrospective summarization, and dependency mapping using tools such as Notion AI, Claude Cowork, GitHub Copilot, and LLM-based assistants. - Champion an AI-first mindset across Product & Engineering. - Integrate launch readiness, enablement, and adoption milestones into core planning and delivery workflows powered by AI. - Run the operating rhythm of the Product & Engineering org: sprint reviews, planning ceremonies, leadership syncs, and quarterly business reviews driven by AI summaries. - Jira Administration & Systems Ownership - Serve as the primary architect and administrator of Coursedog's Jira instance. - Drive adoption of Jira best practices across Product and Engineering. - Strategically manage the broader product tech stack (Jira, Pendo, Tableau, Roadmunk). - Data Management, Reporting & KPIs - Own the build and maintenance of dashboards that surface KPIs across product performance, team execution, sprint delivery, and customer satisfaction. - Define, track, and analyze internal metrics including product profitability, spend allocation, velocity, cycle time, and defect rates. - Establish channels and systems for gathering quantitative and qualitative customer feedback. - Support Operations - Own the operational health of the Support function including SLA frameworks, escalation workflows, and support-to-product feedback loops. - Build a closed-loop system between Support and Product. - Partner with Customer Success and Product leadership to triage high-severity issues. - Identify patterns in support data to proactively surface product quality and documentation gaps. Qualifications - 7+ years of experience in Product Operations, R&D Operations, or Technical Program Management within a B2B SaaS environment. - Deep, hands-on Jira expertise. - Demonstrated track record designing, implementing, and optimizing PDLC processes. - Hands-on experience using AI tools in day-to-day product operations work. - Experience building and maintaining dashboards using BI tools. - Strong analytical and quantitative skills. - Exceptional communication skills with proven ability to operate at the C-suite level. Requirements - PMP, PgMP, or SAFe certification (nice-to-have). - Familiarity with Jira Product Discovery (JPD) and Jira Advanced Roadmaps (nice-to-have). - Experience with customer feedback platforms (nice-to-have). - Experience owning or closely partnering on Support Operations (nice-to-have). - Experience scaling a Product Ops function from early-stage to growth (nice-to-have). Benefits - Healthcare, Dental & Vision: Fixed contribution model promoting equity and transparency. - Retirement Planning: Safe Harbor 401(k) plan with a 4% employer match. - Paid Time Off: Unlimited Paid Time Off policy. - Remote-First Since Inception: Committed to being a remote-first organization. - Equity: All employees are granted equity in the company. - Paid Parental Leave: Up to 12 weeks of fully paid leave for all eligible employees.