Enterprise AI Transformation

AutoPayPlus (AP)
12‑Month AI Transformation Dossier

People First. Remove Steps. Compound Gains.

75%
AI Containment Target
-40%
Average Handle Time
+60%
Outbound Conversion
Core Philosophy

Vision & First Principle — "Remove Steps" at Enterprise Scale

First Principle (Ev Williams)

Find a long‑standing problem and remove steps using technology. At AP, AI is the technology, and people are the source of the solutions. Our aim is to remove steps—clarification meetings, re‑typing, handoffs, rework—so that people can do the work they're paid to do: decide, create, serve, innovate.

Systematic Approach

We make step‑removal systematic by running Kaizen (continuous improvement) in 1‑week cycles, guided by Agile methods, constrained by TOC focus (Voice is the bottleneck), and sharpened by Fractal 80/20 (work on the vital few).

EOS Integration

We wire the whole machine to EOS—Scorecards, Rocks, Issues/IDS (Identify–Discuss–Solve), L10 meetings, and an Accountability Chart that includes AI Employees (digital agents) with named owners and Service Level Agreements (SLAs).

12‑month North‑stars

Voice

  • AI containment ≥ 75% on top intents
  • Average Handle Time (AHT) −25–40%
  • First Call Resolution (FCR) +10–15 pts
  • Customer Satisfaction (CSAT)/Net Promoter Score (NPS) steady or better
  • Zero critical compliance incidents

Growth

  • Outbound conversion +30–60%
  • Legacy reactivation 4–8%
  • Products per member up

Platform (LCFP)

  • Time‑to‑first‑success down
  • Feature adoption up
  • Tickets/100 users down

People

  • ≥ 35% managers at Level‑3 Orchestrator
  • Line staff orchestrate entry‑level agents safely
  • Burnout down

Agility

  • Learning Velocity Index (LVI) ≥ 2–3% weekly
  • Model refresh latency < 24h for critical flows
Technology Stack

Tooling & Collaborations (How We Build)

Repeatable AI Voice Agent Builder Platform

Enables even entry‑level staff to create data‑driven AI Voice agents in minutes using templates, guardrails, and change‑control.

"What Didn't You Use AI For Today?" Platform

Our DAIOP (Daily AI‑Opportunity & ROI Pulse): a 30‑second daily form that captures untapped AI opportunities, time spent, systems touched, and risk—feeding a ranked backlog for the CAIO.

Custom GPT Tools

Custom Generative Pre‑trained Transformer (GPT) tools and low/no‑code (e.g., Genspark.ai) to stand up agents, intake flows, and micro‑apps quickly.

Five9

Telephony platform for voice operations and automation end‑to‑end.

Creatio

Customer Relationship Management (CRM) system for comprehensive customer data management.

EV2

Internal ticketing system for issue tracking and resolution workflows.

Asana

Project management platform for coordinating automation initiatives across teams.

Governance & Quality Systems

Single Source of Truth (SSoT)
Model Registry
Agent Marketplace
App/Prompt Review Board
Month-1 Foundation

Company‑Wide Deliverable Inventory (AutoMatrix)

Everything starts by merging every employee's deliverables into a single inventory, then deciding: keep, kill, automate, or redesign.

1

AutoMatrix Deliverable Inventory (ADI)

Each person lists recurring deliverables (weekly/monthly/quarterly), the Definition of Done (DoD), frequency, audience, time spent, blockers, quality risks, compliance touch‑points.

We collect examples (files, screenshots, transcripts), and upstream/downstream dependencies (who uses it, which system consumes it).

2

Performance Matrix (PMX)

Per deliverable: current cycle time, rework rate, error/exception frequency, SLAs met/violated, business impact (revenue, cost, risk, customer).

Ownership and Accountability Chart seat.

3

Automation Potential Scan

For each deliverable, assess % automatable now vs 90 days (low/med/high confidence).

Flag Voice‑friendly items (e.g., scripted conversations, structured Q&A).

Produce a Go / No‑Go / Redesign recommendation and slot into the Backlog (with RICE—Reach, Impact, Confidence, Effort—TOC impact and 80/20 leverage).

4

Executive Consolidation & Payroll Decision

CAIO consolidates company‑wide deliverables list and presents a Go/No‑Go package to the C‑suite (CEO/COO/CFO) with:

  • Deliverables to continue (with improvement targets)
  • Deliverables to retire (stop paying for them in payroll time)
  • Deliverables to automate (owner + timeline + target % automation)
  • Deliverables to redesign (intake + SOP simplification + pilot plan)

This is an EOS Rock in Q1; the Scorecard tracks time reallocated and automation penetration.

Continuous Improvement

CAIO Continuous‑Improvement Analysis Sessions (CIAS) & Manager Cascade

CAIO CIAS (weekly, "boots‑on‑the‑ground")

Format (60–90 minutes):

Gemba review (observe actual work): watch three real tasks end‑to‑end.
Step removal: one deletion (approval, duplicate entry, meeting) before automation.
Intake or Agent: create/adjust an Intake GPT or Voice agent to handle 80% of the work.
Small‑batch test (10–20 instances); define Friday metric (cycle time, quality, handoffs).
Log in PDCA (Plan‑Do‑Check‑Act) and change‑log; assign owner + SLA.

Who attends:

CAIO, team lead, 1–2 ICs, compliance rep if needed.

Outcome: one measurable improvement by Friday.

Manager‑Led "Mini‑CIAS" (the cascade)

Managers run bi‑weekly 45‑minute sessions with subordinates using the same 5‑step format.

CAIO trains managers via micro‑labs (60–90 minutes):

L2
Practitioner: "Improve one deliverable/week and measure it."
L3
Orchestrator: "Design a small multi‑agent flow; pilot safely; hit the Friday number."
L4
Architect: "Define patterns; approve prompts/apps; mentor; enforce privacy/safety."

Growing Body of Knowledge (GBOK)

Every CIAS/Mini‑CIAS result is captured as a one‑page A3 with before/after data, prompts/scripts, risks & mitigations, and reusable checklists.

Indexed in a Knowledge Graph: by department, intent, deliverable type, and step removed.

The GBOK feeds new Intakes/Agents and becomes the training corpus for AI Voice and GPT tools.

Gamification & Incentives

Leaderboards

Team & individual: hours saved, "first‑pass right," improvements kept for 4+ weeks, DAIOP conversions, risk‑free pilots.

Points → Rewards

Recognition, badges, choice of Innovation Day projects, quarterly bonuses.

Win of the Week

Celebrated in Friday L10 and internal comms.

Executive Level

C‑Suite Innovation, Strategy & SOP Improvement with AI

Executive Decision Companion (EDC)

A CAIO‑managed, privacy‑safe GPT that prepares Board‑grade briefs: market signals, cost curves, scenario trees, Monte‑Carlo ranges, and "what‑if" plays (e.g., "containment +10 pts," "LLM cost −30%," "Five9 rate −12%," "ACH settlement T+0.5").

Outputs: a 1‑page decision memo with assumptions, confidence, and sensitivity.

SOP Simplifier

CAIO runs monthly SOP clinics for CEO/COO/CFO: choose one cross‑functional SOP; strip steps; standardize handoff data; automate first draft; assign Rock if systemic.

Example: Dealer onboarding SOP—remove duplicate approvals; auto‑compose welcome packs; push tasks to Creatio & Asana in one pass.

Vendor/Supply‑Chain & Cash‑Management Plays

Vendor Negotiation

  • Five9: load curves, connect rates, minutes mix; construct RFP with AI; simulate "rate × usage" outcomes; back‑test vendor quotes.
  • LLM providers: token usage by use case; prompt compression/caching; model‑mixing to lower cost/latency at same quality.
  • SMS/email: best send‑windows, deliverability; consolidate vendors; renegotiate on volumes and outcomes.

Cash Management

  • ACH batching vs. intra‑day settlement; optimize float and settlement timing; model regulatorily safe window changes.
  • Chargeback and dispute flow automation (see Card Services); reduce exposure by tightening disclosure and KYC frictionlessly.

Strategic Simulations (quarterly)

Voice‑led growth vs. platform‑led growth vs. dealer‑led growth; staffing plans; ROI curves.

"What if we free 8% payroll hours and reallocate half to Innovation Days?"—simulate product/feature yield.

Innovation Reviews (quarterly)

Review Innovation Day prototypes; green‑light those with highest RICE × TOC × 80/20; resource them as cross‑functional Rocks.

Department Implementation

Department Stories, Agents & Metrics

Every department gets a step‑removal story, agents to build first, metrics, and TOC/80‑20 guidance.

HR — Recruiting, Pre‑Screens, Onboarding, Training, Performance

Narrative

Recruiting Pre‑Screen Voice Agent calls candidates with consent, validates basics, asks role‑specific scenarios, and summarizes strengths/concerns for the hiring manager.

Roleplay Coach trains new phone agents with disclosure‑heavy scenarios, instant feedback on tone, pace, policy.

Onboarding Voice Coach walks new hires through accounts, policy quizzes, and first‑week tasks; posts completion to Asana.

Performance Check‑in Voice Agent gathers monthly reflections; compiles peer feedback; generates a draft review for manager edit.

Agents to ship first

HR Scheduler Recruiting Pre‑Screen Policy Q&A Roleplay Coach Onboarding Coach

Metrics

Time‑to‑schedule; time‑to‑start; candidate NPS; onboarding completion; time managers spend on performance admin.

TOC/80‑20

Top five roles consume most recruiting time; first remove calendar & FAQ friction.

Dev Team — From Sketches to Stories to Releases

Narrative

Design Intake GPT (image‑aware): upload whiteboard photo or wireframe; it extracts components, user goals, edge cases; outputs user stories + acceptance criteria + PRD scaffold; pushes to Asana.

Release Notes Agent: compiles changes + risks + customer impact; posts to Creatio/LCFP help.

Bug Intake Voice/Chat Agent: clarifies steps to reproduce; tags severity; creates EV2 ticket with a reproducible script; suggests owners.

Agents

Design Intake Bug Intake PRD Co‑Pilot Release Notes Dev Q&A

Metrics

DORA (Deployment frequency, Lead time, Change failure rate, MTTR); conversion time from sketch to story; % PRDs needing rework.

TOC/80‑20

A few modules drive most defects; intake clarity is a common constraint—fix with Design/Bug intake.

Card Services & Compliance — Zero‑Defect Disclosures

Narrative

Disclosures & Consent Voice Agent detects jurisdiction; speaks correct disclosure on first utterance; logs consent; hands off.

Dispute Intake Agent gathers complete evidence; prevents "incomplete cases"; opens a compliant case with time‑stamped assets.

Compliance Q&A Agent resolves policy ambiguity; Audit Pack Agent assembles transcripts, consent proof, KYC checks, and system actions.

Agents

Disclosures & Consent Dispute Intake Compliance Q&A Audit Pack

Metrics

Disclosure compliance (target 100%); dispute cycle time; incomplete cases; audit pass rate.

TOC/80‑20

A handful of states & call types produce most risk—lock those first.

Marketing — Intake → Asana → First Drafts

Narrative

Intake Agent replaces clarifying meetings; Asana tasks with user stories, DoD, checklists, and first‑pass drafts (email copy, landing copy, image prompts).

Journey Orchestrator sequences touchpoints; Performance Analyst explains why variant A beat B (audience, timing, subject line, offer).

Agents

Intake Subject‑Line Optimizer Journey Orchestrator Performance Analyst

Metrics

Brief‑to‑first‑draft time; meetings avoided; tests/week; conversion; cost/opportunity.

TOC/80‑20

Top 5 request types cause most delay—standardize those first.

Sales (Dealer) — "Daily Drive" + Objection Handling

Narrative

Daily Drive Agent ranks dealers by ROI potential and optimal call windows; Proposal Drafter outputs decks; Follow‑up Agent writes tailored sequences.

Dealer Roleplay Coach simulates tough conversations; reps rehearse; competence and confidence rise.

Agents

Daily Drive Proposal Drafter Follow‑up Roleplay Coach

Metrics

Meetings booked; time‑to‑proposal; dealer activation; pipeline velocity; close rate.

TOC/80‑20

Top 20% of dealers drive 80% of outcomes—free rep time for those conversations.

Customer Service / Voice — Inbound Solved, Outbound That Converts

Narrative

Already live: KYC, Creatio/EV2 updates (e.g., payment‑date changes), basic outbound.

Next: enlarge intent coverage, harden Assist Panel, tighten handoff payload, and A/B outbound reactivation with SMS/email reinforcement.

Agents

Inbound Greeter & KYC Payment‑Date Change Payoff Quote Address Update Assist Summarizer Outbound Reactivation/Upsell

Metrics

Containment by intent, AHT, FCR, recontacts, CSAT/NPS; outbound answer %, conversion %, revenue/100 calls, opt‑outs.

TOC/80‑20

Voice is the enterprise constraint; exploit it first.

Operations — Exceptions That Route Themselves

Narrative

Data Hygiene Agent fixes common fields; Exception Router assigns right lane automatically; Pre‑flight Checker moves quality gates earlier in the flow.

Agents

Data Hygiene Exception Router Pre‑flight Checker

Metrics

Rework%; cycle time; exception queue age; right‑first‑time%.

TOC/80‑20

A few fields cause most rework—fix those first.

Finance — Close, Narratives, Outliers, Cash

Narrative

Close Reconciliation Agent drafts variance narratives; Outlier Detector flags anomalies; Forecast Explainer translates drivers for non‑finance execs.

Cash‑management models optimize ACH batching/settlement; safe float; chargeback workflows tuned with Card Services.

Agents

Close Reconciliation Outlier Detector Forecast Explainer

Metrics

Days to close; manual adjustments; report errors; time execs spend interpreting numbers.

TOC/80‑20

A few accounts drive most exceptions—automate those narratives.

IT — Access, Health, Knowledge

Narrative

Access Provisioning Agent captures needed info and enforces least‑privilege; Health Sentinel detects repeat faults; Knowledge Drafting Agent updates help docs from solved tickets.

Agents

Access Provisioning Health Sentinel Knowledge Drafting

Metrics

Tickets/week; MTTR; repeat ticket rate; knowledge adoption.

TOC/80‑20

Top 10 request types dominate—automate and self‑serve those first.

Product / LCFP — Every Feature Ships with Its Helpers

Narrative

Feature Tour Builder, Help Synthesizer, Top‑10 Q&A Generator, Nudge Planner ship with each feature; fewer tickets; faster adoption.

Agents

Tour Builder Help Synthesizer Q&A Generator Nudge Planner

Metrics

Time‑to‑first‑success; feature adoption; helpful votes; tickets/100 users.

TOC/80‑20

Top 3 features drive most confusion—treat those first.

Voice Implementation

AI Voice Program (Opportunity Assessment → Build → Sustain)

30‑day assessment produces a ranked backlog of Voice use cases across all departments, with clear owners, SLAs, evaluation sets, and HITL thresholds.

Assessment Phase

30‑day comprehensive assessment produces a ranked backlog of Voice use cases across all departments, with clear owners, SLAs, evaluation sets, and HITL thresholds.

Build Phase

Weekly pilot waves produce small, measurable gains and feed the Agent Marketplace with proven solutions and reusable patterns.

Sustain Phase

The GBOK (Growing Body of Knowledge) becomes the corpus for training Voice and GPT patterns across AP, ensuring continuous improvement and knowledge retention.

Payroll Reallocation → "Google‑Esque" Innovation Days

Freed‑Hours Ledger

Every CIAS/Mini‑CIAS improvement logs hours saved (CFO validates).

Policy:

< 5% freed
Stay in team, run more tests.
5–10% freed
1 day/fortnight as Innovation Day (unscripted, measurable prototypes).
≥ 10% freed
Weekly Innovation Day + Innovation Pods (cross‑functional).

Guardrails:

  • Each Innovation Day yields a shippable improvement (prototype, intake, automation) or a customer‑validated insight;
  • Ideas are scored RICE × TOC × 80/20 and, if compelling, promoted to Rocks.
Decision Framework

Value Assessment & Go/No‑Go Payroll Decisions

Value Score (per deliverable)

F (Frequency) × T (Time) × C (Cost) + Q (Quality risk) + R (Revenue upside) − S (Compliance/Safety risk) = Value Index

Add TOC impact multiplier if the deliverable touches Voice or another bottleneck.

Add 80/20 weight if it sits in the "vital few."

Decision Gates

Go (Continue)

Keep, but target X% cycle‑time reduction and Y% automation in 90 days.

No‑Go (Retire)

Stop paying payroll time; archive.

Automate

Define owner, SLA, and rollout plan; use Repeatable AI tools and Voice Agent Builder.

Redesign

Simplify SOP; introduce Intake; pilot before scaling.

Risk Management

Governance, Safety & Quality (Non‑Negotiables)

SteerCo (AI Steering Committee)

Members: CEO/COO (Chair), CAIO, CFO, Compliance/Legal, Customer Ops, Sales/Dealer, CISO/CTO, Data

Responsibilities: Portfolio, budgets, policy, risk; outputs become Rocks and Scorecard lines.

App/Prompt Review Board

Approves prompts/apps; enforces privacy (PII redaction), security, maintainability, rollback, test coverage; publishes to Agent Marketplace with owner + SLA.

SSoT + Model Registry

Versions of models/prompts/agents; evaluation sets; drift monitors; audit logs.

HITL (Human in the Loop)

Required at risk gates; low confidence → warm transfer with rich handoff.

Disclosures/Consent

100% compliance; state‑aware; logged.

Implementation Timeline

Year Map — Phases with Concurrent Activities

0

Launch, Baselines, Guardrails

Weeks 1–2

SteerCo; Scorecard v1; Voice Quality Charter; DAIOP live; Agent Marketplace v1; Review Board SOP; AutoMatrix Deliverable Inventory (ADI) and Performance Matrix (PMX) kickoff; Automation Potential Scan.

1

Voice Containment & "Two Stories" Live

Months 1–2

Harden Inbound Greeter & KYC, Payment‑Date Change, Payoff Quote; Assist Panel v1; eval sets nightly.

Marketing Intake → Asana (19‑minute pattern) and Design Intake (image→stories) with burndown/burn‑up dashboards.

HR Scheduler, Bug Intake pilots.

Targets: containment +12–18 pts (target intents); AHT −15–25%; QA ≥ 90; 0 critical incidents.
2

Outbound Reactivation & Dealer Toolkit v1

Months 2–5

Persona‑aware outbound waves (voice + SMS/email).

Dealer Daily Drive, Proposal Drafter, Follow‑up, Roleplay Coach.

Card Disclosures & Consent, Dispute Intake.

Targets: 1.5–2.5× conversion lift; cumulative reactivation 1.5–3%.
3

Flywheel Everywhere

Months 4–7

SSoT hardened; model registry; PDCA walls; Deletion Day monthly; L3/L4 cohorts.

LCFP features: tour + help + Q&A + nudge shipped; tickets/100 users down.

Targets: LVI ≥ 2% weekly; critical‑flow refresh < 24h.
4

Personalization & Back‑Office Automations

Months 6–9

Territory Optimizer (Dealer), Finance Close Reconciliation, Ops Exception Router, IT Access Provisioning, Health Sentinel.

Vendor negotiations (Five9, LLMs, SMS/email) and cash‑management improvements.

Targets: DORA improves; tickets down; days to close down; exception queues shrink; vendor rate reductions achieved.
5

Enterprise Intake/Agents & Innovation Days

Months 8–11

Each department's top 5 request types standardized with Intake + first drafts.

Innovation Days routine; Win of the Week & leaderboards keep energy high.

Targets: managers L3 ≥ 35%; AI‑Not‑Used Index down; prototype throughput up.
6

Prove, Audit, Transition

Month 12

Voice excellence audit; Scorecard ROI proof; CAIO Playbook v1.0; Year‑2 portfolio; steady‑state runbooks to AI Ops & Review Board.

Operating Cadence

Weekly / Monthly Operating Rhythm (EOS‑Native)

Weekly Rhythm

Monday
90m

Choose 2 company targets (often Voice + Platform); each department picks 1 deliverable; define Friday metric; add Issues to L10.

Tuesday
60–90m/team

Delete one step; build/adjust Intake/Agent; prep a 10–20 item test.

Wednesday
60m

Run test; capture time/quality/compliance.

Thursday
60–90m

Review/fix; expand if safe.

Friday
60m

Scorecard; IDS top 3 Issues; Win of the Week; update Leaderboards; log Freed‑Hours Ledger.

Monthly & Quarterly Rhythms

Monthly

  • Kaizen Blitz (1 day) per value stream;
  • Deletion Day (retire ≥1 manual step per squad);
  • SteerCo (portfolio, budget recode, vendor updates, cash‑flow plays).

Quarterly

  • Rocks refreshed;
  • L3/L4 certifications;
  • Innovation Reviews;
  • Platform roadmap checkpoint;
  • Payroll reallocation checkpoint.
Key Performance Indicators

Metrics Decision‑Makers Will See (every Friday)

Voice (Inbound)

Containment (by intent) AHT FCR Recontacts QA CSAT/NPS 0 critical incidents

Voice (Outbound)

Answer % Conversion % Revenue/100 calls Opt‑outs

Platform (LCFP)

Time‑to‑first‑success Adoption Helpful votes Tickets/100 users

HR/Dev/Card/Marketing/Sales/Ops/Finance/IT

One weekly number per top deliverable (speed, quality, cost, happiness)

Capability

% Level‑2 % managers Level‑3 # Level‑4 # approved prompts/apps Duplication trend

Flywheel

LVI Model refresh latency Eval pass rates

Repository (DAIOP)

AI‑Not‑Used Index # items converted Freed‑Hours Ledger

Innovation

# Innovation Days Prototypes Time‑to‑concept % promoted to Rocks

Vendor & Cash

Blended rate per minute/token/SMS/email ACH settlement timing Float realized Chargeback cycle time

Example Artifacts (ready to drop in)

Agent Card (owner + SLA + eval set + HITL gates + version log)
Handoff Payload (JSON)—rich context for warm transfers
Design Intake Output—user stories & acceptance criteria from images
PDCA One‑Pager—problem → countermeasure → small‑batch → result → next
Feature Readiness Checklist—tour, help, Q&A, nudge, telemetry, support tags
Vendor/Rate Analysis Template—minutes, tokens, messages; rate simulation; RFP draft
Cash‑Flow Optimizer—ACH batch windows, settlement timing, working‑capital effect

Why this version will land with the decision‑makers

It is vivid and real.

We begin with Marketing Intake GPT (19 minutes → 100–200+ hours/month) and Sketch‑to‑Stories (images → user stories), then replicate that remove‑steps pattern department by department, including HR recruiting voice interviews, Card Services disclosures/disputes, and Dealer Daily Drive routing.

It includes the missing engine.

The CAIO Continuous‑Improvement Analysis Sessions (CIAS), manager‑run Mini‑CIAS, the Growing Body of Knowledge (GBOK), gamified leaderboards, and Innovation Days are now fully spelled out and tied to freed payroll hours.

It covers the money.

Vendor renegotiations (Five9, LLMs, SMS/email), cash‑management (ACH batching/settlement), and chargeback efficiency are explicit CAIO workstreams.

It puts payroll to work.

The AutoMatrix Deliverable Inventory (ADI) and Performance Matrix (PMX) enable Go/No‑Go/Automate/Redesign decisions so you stop funding low‑value deliverables and aggressively automate the rest.

It's EOS‑native.

Every improvement appears on the Scorecard, becomes a Rock when big, and is solved via L10/IDS when blocked. The Accountability Chart includes AI Employees with owners and SLAs so the culture endures.