Head of Product Operations and AI Transformation

About SecurityScorecard

SecurityScorecard is the global leader in cybersecurity ratings, with over 12 million companies continuously rated, operating in 64 countries. Founded in 2013 by security and risk experts Dr. Alex Yampolskiy and Sam Kassoumeh and funded by world-class investors, SecurityScorecard’s patented rating technology is used by over 25,000 organizations for self-monitoring, third-party risk management, board reporting, and cyber insurance underwriting; making all organizations more resilient by allowing them to easily find and fix cybersecurity risks across their digital footprint.

Headquartered in New York City, our culture has been recognized by Inc Magazine as a "Best Workplace,” by Crain’s NY as a "Best Places to Work in NYC," and as one of the 10 hottest SaaS startups in New York for two years in a row. Most recently, SecurityScorecard was named to Fast Company’s annual list of the World’s Most Innovative Companies for 2023 and to the Achievers 50 Most Engaged Workplaces in 2023 award recognizing “forward-thinking employers for their unwavering commitment to employee engagement.” SecurityScorecard is proud to be funded by world-class investors including Silver Lake Waterman, Moody’s, Sequoia Capital, GV and Riverwood Capital.

About the Team

SecurityScorecard runs an unusually fast product org — ~120 in Engineering, a roadmap that re-prioritizes weekly, and a culture where the question isn’t “can we build it in two months” but “how do we do it in five days?” Product Operations is the operating system that lets that speed scale without flying blind.

We’re hiring a leader to own Product Ops end-to-end and run it as a three-pillar function: Data, Stories, and Process. This person inherits a mature, AI-native operation and is expected to push it further.

You’ll be the connective tissue between PMs, Engineering, Design, GTM, Finance, and the board reporting line. You break bottlenecks, you instrument everything, and you’re already prototyping the next AI workflow before anyone asks for it.

About the Role

Data & Product Metrics (obsessively)

• The metrics source of truth: Threshold Score (customer health → board + Gainsight), engineering delivery metrics (Span/DORA, throughput, AI-code ratio via Sigma), product engagement & NPS methodology (Pendo Listen), and Product P&L inputs with Finance.
• The Customer Insights data layer on Snowflake — AI-extracted pain points, feature requests, and verbatim quotes piped from call transcripts — and the persona-matching model against our maturity frame work.
• You should itch when a roadmap call happens without the data behind it.

Programs, Reporting & Delivery (PMO)

• The full delivery cadence: roadmap intake, Jira (PRODF) administration, R/Y/G milestone tracking, the Change Control Board (CCB), release-train sign-off, OKRs, and planning for ~120 people.
• The weekly executive reporting stack (Joint Tech & Product update, Q2 Roadmap Exec Report, Engineering Weekly) and the quarterly board-paper KPI inputs and you’ll formalize these so they don’t live in one person’shead.

AI for Product Ops (the urgent mandate)

• Inherit and extend a working library of Claude skills that already run this operation — weekly reporting, CCB recaps, customer-meeting research,
• Pendo-feedback-to-roadmap matching, hiring protocols, release-notes ROI framing wired across systems such as Jira, Confluence, Pendo, Snowflake, Slack, GDrive.
• Become the org’s go-to for AI/agentic product-ops tooling (today an informal role across Product, CS, and Marketing) and turn ad-hoc magic into durable, documented capability. This is where we want urgency and excitement, not caution.

Cross-functional forums & GTM

• Run the forums that keep the org aligned: Product Court (GTM Product roadmap triage), Bar Raisers (work-quality review), and the monthly product-org meeting.
• Partner on pricing & packaging (Titan Secure/Assess), the annual Pricebook, vendor management (Pendo, Sigma, Span, FullStory, Heap), and strategic customer/roadmap calls.

Who you are

• A brick-wall breaker. You see a blocker and go through it smart, allergic to “that’s how we’ve always done it.” We reward bias to action.
• Impatient (yet personable/friendly), in the best way. You compress timelines and force decisions (Pendo/Heap consolidation, release sign-offs, planning logistics) without burning the team out. You thrive in constant re-planning and design work to be incremental and portable.
• Metrics-obsessed. You think in cohorts, leading indicators, and ROI. You can build the dashboard and tell the story it implies — to a PM and to the board.
• Genuinely AI-forward. You’ve shipped AI/LLM workflows into how work gets done, not just talked about it. You’ll walk in excited to scale our Claude-native operation.
• A CPTO/PM force-multiplier. You give senior PMs leverage, not overhead, and you operate as a true partner to the CPTO and the co-founders.

Required Qualifications

• 8+ years in Product Operations, PMO, or product/program leadership — including building or scaling a Product Ops function in a fast B2B SaaS org (cybersecurity a plus).
• Run delivery cadence across a multi-PM / multi-squad org; 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 — you set the pace, you don’t wait for it.
• You need to be fluent in Claude and other AI tools. If you are not, please do not apply.

How you’ll fit at SecurityScorecard

We value urgency, ownership, and people who’d rather break the wall than file a ticket about it — the same instinct behind “do it in five days” and forums like Product Court. There’s a real, healthy tension here between speed and operating maturity; your job is to add the maturity without killing the speed. If reading this made you impatient to start fixing things that’s a great signal.

Benefits

Specific to each country, we offer a competitive salary, stock options, Health benefits, and unlimited PTO, parental leave, tuition reimbursements, and much more!

The estimated total compensation range for this position is $325,000 - $350,000 (base plus bonus). Actual compensation for the position is based on a variety of factors, including, but not limited to affordability, skills, qualifications and experience, and may vary from the range. In addition to base salary, employees may also be eligible for annual performance-based incentive compensation awards and equity, among other company benefits.