Head of Product Operations and AI Transformation

SecurityScorecard•New York City, NY

20h•Onsite

About The Position

SecurityScorecard is seeking a Head of Product Operations and AI Transformation to lead their Product Operations function end-to-end. This role is crucial for enabling the speed and scale of a fast-paced product organization. The function is structured around three pillars: Data, Stories, and Process. The ideal candidate will inherit a mature, AI-native operation and be expected to advance it further. This individual will serve as the connective tissue between various departments including PMs, Engineering, Design, GTM, Finance, and the board. Key responsibilities include breaking down bottlenecks, instrumenting processes, and proactively prototyping AI workflows. The role requires a strong bias for action, a metrics-obsessed mindset, and genuine enthusiasm for AI/LLM workflows. The company culture values urgency, ownership, and a proactive approach to problem-solving, balancing speed with operating maturity.

Requirements

8+ years in Product Operations, PMO, or product/program leadership.
Experience building or scaling a Product Ops function in a fast B2B SaaS organization (cybersecurity experience is a plus).
Experience running delivery cadence across a multi-PM / multi-squad organization.
Deep Jira fluency.
Hands-on use of AI/automation to change how product work gets done.
Fluent across the modern product stack: Pendo, Sigma/Snowflake-backed BI, Span (or DORA tooling), Jira, Confluence.
NYC-based and comfortable in a high-velocity, high-accountability culture.
Fluent in Claude and other AI tools. Applicants not fluent in these tools should not apply.

Nice To Haves

Experience with cybersecurity a plus.

Responsibilities

Serve as the metrics source of truth, managing Threshold Score (customer health), engineering delivery metrics (Span/DORA, throughput, AI-code ratio), product engagement & NPS methodology, and Product P&L inputs.
Manage the Customer Insights data layer on Snowflake, including AI-extracted pain points, feature requests, and verbatim quotes, and the persona-matching model.
Oversee the full delivery cadence, including roadmap intake, Jira administration, R/Y/G milestone tracking, Change Control Board (CCB), release-train sign-off, OKRs, and planning for approximately 120 people.
Manage the weekly executive reporting stack (Joint Tech & Product update, Q2 Roadmap Exec Report, Engineering Weekly) and quarterly board-paper KPI inputs, formalizing these processes.
Inherit and extend the library of Claude skills for weekly reporting, CCB recaps, customer-meeting research, Pendo-feedback-to-roadmap matching, hiring protocols, and release-notes ROI framing.
Become the organization's go-to for AI/agentic product-ops tooling, turning ad-hoc magic into durable, documented capability.
Run cross-functional forums such as Product Court (GTM Product roadmap triage), Bar Raisers (work-quality review), and the monthly product-org meeting.
Partner on pricing & packaging, the annual Pricebook, vendor management (Pendo, Sigma, Span, FullStory, Heap), and strategic customer/roadmap calls.