30-60-90 Day Plan

Building an AI-Forward Product Management Practice

A rollout plan for standing up a repeatable PM 'operating system' that improves clarity, alignment, and speed of learning—while making AI a first-class accelerator in how Product does its work.

Why This Rollout

ChiroHD's competitive advantage is already clear: an integrated, cloud workflow and strong support/customer experience. The competitive landscape also shows where incumbents and adjacent platforms can still out-muscle a newer entrant—especially in advanced billing/RCM depth and analytics/reporting maturity.

This plan is intentionally not a feature roadmap. It's a rollout for building a high-functioning PM practice that makes decisions faster, shortens the research-to-insight cycle, improves delivery predictability, and uses AI to multiply output from a small team.

Outcomes by Day 90

1

A clear PM operating model (cadences, artifacts, decision rights) that the org can follow without heroics.

2

A durable customer insight pipeline (support + sales + VOC + competitive intel) with measurable throughput.

3

A predictable prioritization and roadmap mechanism tied to outcomes + evidence, not opinion.

4

AI embedded into daily PM work (research, synthesis, drafting, analysis, prototyping, comms) with security guardrails.

5

Executive visibility: a monthly "Product Outcomes Review" with 3–5 decisions, 5–10 learnings, and metric trends.

Guiding Principles

AI drafts, humans decide

AI accelerates research, synthesis, and first drafts; leaders own judgment and tradeoffs.

Outcomes over outputs

Roadmaps express measurable outcomes; features are a means.

Small-team leverage

Pick tools + rituals that amplify the team you have (not processes you can't staff).

Security-by-design

No PHI or sensitive customer info in non-approved tools; default to anonymization + redaction.

One source of truth

Roadmap, decisions, learnings, and key artifacts live in a single discoverable workspace.

The 90-Day Rollout

Days 1–30

Foundation

"Stand up the operating system and demonstrate 2–3 undeniable AI "speed wins.""

Key Objectives

  • Create a predictable intake→decision→delivery loop.
  • Establish continuous discovery and a shared language for prioritization.
  • Teach the team to use AI as a force multiplier (and do it safely).

PM Fundamentals

  • Define roles & decision rights
  • Backlog + intake redesign
  • Prioritization model v0
  • Roadmap framing (outcomes, not features)
  • Launch rituals

AI Enablement

  • AI onboarding workshop
  • Prompt packs v1
  • Showcase: Competitive landscape refresh
  • Showcase: Support → insight pipeline
  • Showcase: PRD-lite time reduction

Deliverables

PM Playbook v1Roadmap v1 (outcome-based)VOC pipeline v1AI prompt library v1 + policy v1
Days 31–60

Operationalize

"Turn the system into muscle memory and tighten the research→decision loop."

Key Objectives

  • Increase throughput of validated learning.
  • Improve delivery predictability by tightening requirements + dependency clarity.
  • Expand AI usage from "cool demos" to standard workflow steps.

Discovery Maturity

  • Customer conversation cadence (2–4/week)
  • Discovery repository
  • Assumption tracking
  • Lightweight segmentation

Delivery Maturity

  • PRD-lite becomes the norm
  • Definition of Ready / Done
  • Release comms standardization

AI Embedded

  • Weekly AI triage pack
  • Analytics Q&A habit
  • Rapid prototyping for validation

Deliverables

Product Strategy v1 + North Star metricsRoadmap v2 with assumptionsDiscovery repository v1PRD-lite workflow adopted
Days 61–90

Institutionalize

"Make the practice resilient, measurable, and scalable—without adding drag."

Key Objectives

  • Lock in the operating system as "how we work."
  • Establish governance for portfolio tradeoffs and AI usage.
  • Create a plan to scale (people, skills, tooling) as the company grows.

Portfolio & Governance

  • Quarterly planning playbook
  • Portfolio review
  • Stakeholder comms model

AI Governance

  • AI usage policy v2
  • Prompt library v2
  • Team enablement workshops
  • PM Copilot blueprint

Scale Plan

  • Role clarity & hiring plan
  • Metrics & feedback loops

Deliverables

PM Operating Model v2 (locked)Quarterly planning packageAI governance packagePM Copilot blueprintCEO readout: wins, metrics, next 2 quarters

The Operating System

Core Cadences

Weekly (60 min)

Product Triage + Decisions

Top VOC themes, support escalations, sales asks, churn reasons, competitive signal deltas

Biweekly (45–60 min)

Discovery Review

What we learned, what changed, what we're validating next

Monthly (60 min)

Product Outcomes Review

Outcomes trends, risks, key bets, key decisions required (CEO + VP Product + Eng Lead)

Quarterly (2–3 sessions)

Strategy & OKR Planning

Outcomes/OKRs, capacity allocation, "kill list," key assumptions

Standard AI Workflows

Competitive Analysis

< 60 minutesmonthly refresh

Weekly VOC Pack

Every Mondaytop 5 themes + discovery bets

PRD-lite Generator

As needed50–70% reduction in first-draft time

Exec Update Generator

Weeklywhat shipped, learned, risks, asks

See the features this practice would help ship: ChiroSwitch Migration Studio | Intake-to-Exam Smart Notes

Or read the competitive analysis that informed these recommendations.