Head of Product Operations and AI Transformation

SecurityScorecard•New York, NY

6h•$325,000 - $350,000•Onsite

About The Position

SecurityScorecard is seeking a leader to own Product Operations end-to-end, focusing on a three-pillar function: Data, Stories, and Process. This role inherits a mature, AI-native operation and is expected to drive it further. The Head of Product Operations will serve as the connective tissue between PMs, Engineering, Design, GTM, Finance, and the board reporting line, aiming to break bottlenecks, instrument everything, and proactively prototype AI workflows. The position requires a strong bias for action, impatience in driving decisions, a metrics-obsessed mindset, and genuine AI-forward thinking, with a focus on scaling an AI/agentic product-ops tooling capability. The role is based in NYC and operates within a high-velocity, high-accountability culture.

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).
Ability to run 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

Cybersecurity experience.

Responsibilities

Own Product Ops end-to-end as a three-pillar function: Data, Stories, and Process.
Serve as the connective tissue between PMs, Engineering, Design, GTM, Finance, and the board reporting line.
Break bottlenecks, instrument everything, and prototype the next AI workflow.
Manage the metrics source of truth, including customer health, engineering delivery metrics, product engagement & NPS methodology, and Product P&L inputs.
Oversee the Customer Insights data layer on Snowflake, including AI-extracted pain points, feature requests, and verbatim quotes.
Manage the full delivery cadence: roadmap intake, Jira administration, milestone tracking, Change Control Board (CCB), release-train sign-off, OKRs, and planning for approximately 120 people.
Manage the weekly executive reporting stack and quarterly board-paper KPI inputs, formalizing these processes.
Inherit and extend a working library of AI skills (e.g., Claude) for weekly reporting, CCB recaps, customer-meeting research, 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 including Product Court, Bar Raisers, and the monthly product-org meeting.
Partner on pricing & packaging, the annual Pricebook, vendor management, and strategic customer/roadmap calls.
Break down obstacles and drive action with a bias for action.
Compress timelines and force decisions without burning the team out, designing work to be incremental and portable.
Build dashboards and tell the story implied by data to both PMs and the board.
Scale the AI/LLM workflows into how product work gets done.
Provide leverage to senior PMs and operate as a true partner to the CPTO and co-founders.