Director of Product Management, Agent-Native Web Experiences

Leadout Capital; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Job summary

Leadout Capital is seeking a Director of Product Management for the Digital Marketing Technology team to evolve our brand and practitioner-facing websites into an AI-native, human-led ecosystem. You will drive a rapid, spec-driven approach where agent-enabled experiences expand user intelligence and site performance.

You’ll own the end-to-end roadmap, the user experience, design partners, and pilot programs, collaborating with engineers, design, and business stakeholders to ship impactful

Qualifications

• 5+ years shipping products for technical users.
• Fluency with AI and coding agents, including orchestration and evaluation frameworks.
• Strong prototype-to-execution capability in ambiguous environments.
• Excellent written and verbal communication across cross-functional teams.
• Ability to distill customer pain into product requirements.

Responsibilities

• Set and own the roadmap, outcomes, and product strategy for brand and role-based websites.
• Own the user experience; partner with design to earn partner, customer, and community trust.
• Define success metrics and make trade-offs; kill projects that aren’t delivering value.
• Prototype with coding agents before writing specs; run against real data and iterate.

Skills

PM Experience

AI & Coding Agents

Execution Mindset

Cross-functional Leadership

Customer Empathy

Education

Bachelor's degree in technical, business, or analytical discipline

Tools

Claude Code

Cursor

Replit

LangSmith

Langfuse

Job description

The Role

As the Director of Product Management on the Digital Marketing Technology team, you will lead the strategic evolution of our brand and practitioner-facing websites portfolio into an AI‑Native, Human‑Led ecosystem. You wlll be responsible for transforming our digital presence from static experiences into an intelligent, agentic web where Al is an extension of the user's intellect. Your mandate is to lead the shift from traditional development cycles to rapid‑innovation, spec‑driven environment where brand vision is machine‑readable and executable by agents.

You’ll own the roadmap, the user experience, the design partners and pilot programs.

This is an IC role for a builder who thinks in agents. You use coding agents (Claude Code, Cursor, Codex, etc.) daily and have a point of view on where they're going. You prototype before you spec. You treat an agent like a co-worker — not a tool you prompt once and forget, but a collaborator you brief, course‑correct, and build trust with over time. You know how to set context, divide work, and close the loop when an agent goes off the rails. You've built and evaluated agents yourself, and you have opinions about what makes agent optimization actually work — evaluation harnesses, annotation flows, failure clustering, and the feedback loops that turn raw session data into product intelligence.

What You’ll Do

Own the product end to end

• Set and own the roadmap, outcomes, and product strategy for our brand and role-based websites.
• Own the user experience. Partner with design to build sites that our business partners, customers, and communities trust and reach for, not one they tolerate.
• Set and defend success metrics (pilot activation, failure-cluster coverage, recommendation acceptance, agent quality lift) and use them to make real trade-offs. Kill what isn't working.

Build, don't just describe

• Prototype with coding agents to pressure-test ideas before writing a spec. A working demo beats a 10-page doc.
• Dogfood the product constantly. Run it against real customer data. Break it. Eval it. Bring receipts.
• Stay close to the code and the runtime. Read the traces. Understand the eval harness. Sit next to engineering during discovery.

Run the customer program

• Run the design partner program directly. Lead pilot calls, extract requirements, turn customer pain into shipped product.
• Bring the customer voice into every product decision. Distinguish real needs from workarounds, one-offs, and badly framed requests.

Move fast and coordinate across the portfolio

• Push a fast-paced environment. Ship the smallest thing that works, learn, iterate.
• Coordinate with peer PMs across Digital Marketing Terchnology — the runtime, the authoring surfaces, evaluation, and the broader Observability portfolio — fits into the ADLC as one coherent story.
• Communicate clearly with engineers, designers, execs, and business partners. Bring a point of view and change your mind when the data says to.

Required Qualifications

• Product Management Experience: 5+ years of experience shipping products for technical users (developers, admins, or SMEs). Proven track record of scope and impact in an enterprise or startup environment.
• AI & Coding-Agent Fluency: Daily user of coding agents (Claude Code, Cursor, etc.). Substantive knowledge of LLM orchestration, tool use, and evaluation frameworks (evaluation harnesses, annotation flows, failure clustering).
• Builder and Execution Mindset: Comfortable with ambiguity and biased for action. You prototype early to pressure-test ideas and turn fuzzy problems into sharp bets with measurable outcomes.
• Communication & Cross-functional Leadership: Strong written and verbal communication skills. Ability to rally teams across engineering, design, and operations while holding your own with executives.
• Customer Empathy at Scale: Ability to synthesize signals across a design partner cohort and distill customer pain into crisp product requirements and shipped products.

Preferred Qualifications

• Bachelor's degree in a technical, business, or analytical discipline.
• Engineering background, or the equivalent hands‑on depth — comfortable reading code, reviewing APIs, prototyping in a notebook, and partnering with engineers on real trade-offs.
• Direct experience with the current agent-building and eval landscape (Cursor, Claude Code, Replit, LangSmith, Braintrust, Langfuse, agent frameworks, headless CMS) and strong opinions on what they get right and wrong.
• Experience with websites, customer‑facing pilot or design‑partner programs for early‑stage AI products.
• Prior experience on a 0-to-1 or innovation team.
• Design sense: can turn messy systems into clean primitives with opinionated defaults.
• Experience operating with autonomy in a highly cross‑functional environment, including executive, technical, and go‑to‑market stakeholders.
• Experience with CRM and Marketing Technology ecosystems, Web design, Slack, and Contentful.