Product Portfolio

Proactive, Action-Taking AI for the Enterprise

A product requirement document written in response to a PM interview exercise from a leading leading enterprise AI company. Presented here as a portfolio piece.

RS
Ralf Konrad Schiffert — Principal Product Manager. 10+ years owning API platforms and developer ecosystems at scale. Former API & Developer Platform PM at Cisco Webex (50K developers, 800 ISVs, 8B API invocations/month). Earlier: Twilio, Nuance Communications. Based in San Jose, CA.
ralf@schiffert.me  ·  LinkedIn

Product Manager PRD Prompt — Proactive, Action-Taking AI

The Problem: Most AI tools today are reactive: you ask, they answer. But the biggest unlock for knowledge workers isn't a better answer engine. It's an agent that works alongside you: observing, anticipating, and acting across your company's tools without being asked.

This is a fundamentally different product from what exists today. It changes the user's relationship with AI from "tool I use" to "coworker that works for me." It also introduces new challenges: How does it earn trust? What happens when it's wrong — and the action was permanent?

Your Task: Write a PRD covering two stages:

MVP — 3 engineers, 3 months. Define the MVP, who it solves it for, what it does, and how you'd measure success.

MVP + 3 Months — Highlight the next two capabilities you would add and why.

Explore: personalization, rollout and trust-building, use of AI, and competitive differentiation.

3 Engineers · 3 Months Enterprise AI Proactive Agents Trust Architecture

From Answer Engine to Enterprise Coworker

A governed skill platform for proactive AI in the enterprise

The enterprise has an AI problem that isn't really an AI problem. The models are capable. The tools are available. What's missing is trust — enterprise trust that agents won't leak data, violate governance, or act beyond their authority. And user trust that the agent actually understands them as individuals, not just as roles.

The vision is an enterprise AI coworker that earns both. For the enterprise: a governed skill platform where every agent action is vetted, bounded, auditable, and controlled by IT. For the user: an agent that learns what you love and what you loathe — in your own words, every week — and quietly takes away the work that drains you.

What We Are Really Building

Consider a moment most knowledge workers know. It's Tuesday afternoon. You have a document open — a monthly status deck, a backlog update, a report you fill in the same way every time. You've had it open for forty minutes. You haven't touched it. You close it and open something else.

The Tuesday Afternoon Moment
The agent sends a quiet message: "I noticed you've been working on the Q3 status update. I have a sense this isn't your favorite part of the job. Want me to draft an update from your recent project activity?"

You didn't ask. You didn't flag it. But the agent knew — because it has been learning what you love and what you loathe, in your own words, every week. That is not a productivity feature. That is a trusted colleague.

1. Why Proactive AI Has Failed in Enterprise

The technology exists. The trust doesn't.

MIT's NANDA study found that only 5% of organizations exploring AI reach production with measurable impact. Deloitte found that only 11% of piloted agents reach production. Gartner predicts 40% of agentic AI projects will be canceled by end of 2027.

The most capable open-source proactive agent today runs as an always-on background agent that observes your files, email, and calendar and acts without being asked. Within 90 days of launch, 1,184 malicious skills were confirmed in its marketplace and a critical vulnerability allowed attackers to inherit every permission and tool connection of their victim. One enterprise security lead called it "groundbreaking from a capability perspective and an absolute nightmare from a security perspective."

The problem is not building a proactive agent. The problem is building one that an enterprise can actually trust to run.

Two trust deficits must be addressed simultaneously:

The user trust deficit. Most proactive agents guess what to automate from behavioral patterns — and get it wrong. Users disengage when the agent optimizes tasks they actually enjoy, and without explicit preference data, the agent never corrects course.

The enterprise trust deficit. IT and security teams don't know what the agent is accessing, what actions it might take, or how to govern it. Without answers, they don't deploy.

The path to a fully proactive enterprise coworker is not a model problem. It is a trust architecture problem — and it must be solved at both levels simultaneously.
The Tuesday afternoon moment

2. Why This Company Is Uniquely Positioned

Most proactive agent projects stall before they start — negotiating the data access that this platform already has.

The Enterprise Knowledge Graph knows the enterprise. Org structure, team composition, what people are working on, how information flows. A proactive agent built on this foundation has enterprise context as a starting point — something a competitor must spend months negotiating to get.

Read access is already granted. A competitor faces months of negotiation with IT just to access email and a handful of Slack channels. This platform skips this entirely. That is not a feature advantage — it is a time-to-value advantage measured in months.

Write access is already built. With over 100 enterprise connectors, the platform can already take actions in the systems that matter — scheduling meetings, submitting to HR systems, updating project tools — using integrations IT has already vetted and approved.

CategoryCompetitorKey Limitation
Suite assistantMicrosoft CopilotFragmented outside Microsoft ecosystem; no cross-tool enterprise graph
Suite assistantGoogle Workspace AINo enterprise trust relationship; faces same access negotiation
General-purpose agentClaude Cowork (Anthropic)No enterprise knowledge graph or cross-tool context
Open-source frameworkOpenClaw / HermesNo data grounding, governance, or connectors — enterprises must build all of this themselves

3. The MVP — Enterprise Proactive Skill Platform

Personal Context
I spent several years as the only remaining API PM at a Fortune 100 company, managing dozens of simultaneous workstreams. Every week I handled things that mattered. Every week my 1:1 with my manager covered maybe 10% of it — whatever happened to be most recent or loudest. The rest was invisible. This isn't just my problem. It is the default condition for most knowledge workers at enterprise scale.

The path to a fully proactive enterprise coworker is paved with small, trusted actions. We start with one skill that every knowledge worker needs, in a portal that every IT team can govern, on a knowledge graph that every enterprise already trusts.

The Enterprise Skill Portal

A lightweight governed catalog — not a marketplace. IT admins approve skills and assign user groups via existing directory integration (Microsoft Entra ID). Users browse and enable approved skills. The portal provides:

User-contributed skills are supported from day one — a skill is a structured document submitted through the portal, activated only after IT admin approval.

The 1:1 Prep Skill — The First Skill

Every week the skill monitors the user's activity across connected tools: meetings attended, messages sent and received, documents created or edited. 24 hours before the scheduled 1:1, it surfaces a structured summary organized by workstream. The user reviews, edits, and approves. On approval, the agent sends it to the manager as a pre-read.

The skill also captures the engagement survey most enterprises require — drafting responses to "what did you love this week?" and "what did you loathe?" for user review before submission. This loathe signal is the mechanism that makes the agent genuinely understand the user over time. Not behavioral inference — explicit, grounded preference data in the user's own words.

The Trust Escalation Arc

Stage 1 · Weeks 1–4

Supervised

Full user review and explicit approval before anything is sent. The agent shows its work. Nothing leaves without sign-off.

Goal: demonstrate accuracy
Stage 2 · Weeks 5–8

Assisted

User sets a preference: "send automatically if I haven't reviewed by two hours before the 1:1." First experience of low-friction automation.

Goal: demonstrate reliability
Stage 3 · Weeks 9–12

Autonomous

User opts into background mode. Summary generated and sent without review. Post-send notification with easy correction mechanism.

Goal: demonstrate trust was earned
ActionRisk LevelDefault
Draft weekly summaryLowAuto-generate
Draft engagement survey responsesLowAuto-generate
Send summary to managerMediumRequires approval → optional autonomy after track record
Schedule 1:1 meetingLowAuto-schedule after opt-in
Submit to HR systemMediumRequires approval
Publish skill to portalHighAlways requires IT admin approval

Why This Skill First

Universal immediate value — every knowledge worker with a manager has this problem. Low risk — nothing leaves without approval in Stage 1. Explicit preference data — the loathe signal collects grounded user-stated preferences rather than guessing from behavior. Tactical trust — the three-stage arc proves the agent is accurate before asking for more autonomy. Strategic trust — the loathe signal is the foundation for the Tuesday afternoon moment.

Something less obvious happens over time. One week the user reads the skill's draft of "what I loathed" and recognizes it immediately — something they hadn't yet put into words themselves. That moment is the beginning of strategic trust. The system has demonstrated it understands the emotional texture of their workweek — not just what they did, but how they experienced it.
1:1 Prep skill interface

4. Success Metrics

North star: Successful autonomous actions per weekly active user — the number of times the platform completed a task on a user's behalf without requiring approval. This is the single number that tells us whether we have moved from reactive to proactive.

Value
Time saved on 1:1 prep (self-reported)
Manager pre-read usefulness (survey)
Quality
Approval-without-edit rate
Action reversal rate
Trust
Autonomy adoption rate
Autonomy retention rate
Autonomy revocation rate

The leading indicator: Approval-without-edit rate combined with continued usage and low reversal rate. These three signals together — not any one alone — tell us whether trust is being earned or assumed.

Compounding trust flywheel

5. MVP + 3 Months: Two Next Capabilities

Active Skill Recommendation Engine

Makes discovery active — surfacing relevant skills based on role, team, and the accumulated loathe signal. Embedding similarity between what users have said they loathe and available skill descriptions tells the engine what to surface. "You've mentioned expense reports three weeks running. There's a skill for that." The skill library expands through platform-built additions, user contributions, partner skills, and cross-enterprise sharing.

Governance Supervisor Agent

As the skill library grows, manual IT admin review becomes a bottleneck. The Governance Supervisor Agent learns from the existing review process and uses LLM-based policy matching to automate vetting — IT reviews exceptions, not every submission.

The supervisor agent then becomes the foundation for the long-term vision: informed by the accumulated loathe signal, the proactive agent identifies a recurring draining task and writes a candidate skill to address it. The supervisor validates that skill against enterprise policy. If it passes, the skill is available immediately — and optionally published for colleagues to discover.

The agent doesn't just automate work. It figures out which work to automate — and builds the solution itself.

This is how the vision becomes real. Not through a general-purpose autonomous agent deployed all at once — but through a governed ecosystem of trusted skills, orchestrated by a supervisor that knows the enterprise, grounded in what each user explicitly said they need, earning more autonomy one verified action at a time.

The agent that knows what you loathe — in your own words, every week — is the agent that earns the right to work for you.