learn-ai-finance-with-phoebe / Leader session 6 of 6
Learn AI + Finance with Phoebe · Leader track · Session 6 of 6

Strategy & the 24-month roadmap: from bets to a board-ready plan

This is the finale of the leader track. You have a landscape (a1), a use-case map (a2), guardrails (a3), a team plan (a4), and a business case (a5). Now you sequence it all into a strategy your board can back: a realistic view of where finance AI is heading over the next 24 months, an order to do things in that does not skip the foundation, and a single board slide that tells the whole story - where you are, the bet, the guardrails, the milestones, and the ask.

🟠 Leader track Leaders: CFO · FP&A leadership No code, ever 45 min
0-3 · Intro 3-18 · The agentic future, realistically 18-33 · Sequencing the portfolio 33-45 · The board narrative + exercise
Part 0

Why this session exists

A pile of good use-cases is not a strategy. What turns them into one is sequence and story - the order you do them in, and how you explain the whole thing to the people who hold the budget. This finale hands you both. First we look honestly at where finance AI is actually going over the next 24 months, so your plan is ambitious without being fantasy. Then we sequence the portfolio so the foundation comes first - because skipping it is the single most reliable way to make good pilots fail. Finally we build the one board slide that carries the whole plan.

Live - presented in session Self-study - read after class ★ Questions for your team Official sources covered
★ What you walk out with today A sketch of your own 24-month roadmap - now, 6, 12, and 24 months, each with a theme and a couple of concrete moves - and the outline of a single board slide that tells the story end to end: where we are, the bet we are making, the guardrails, the milestones, and the specific ask. Everything from a1 through a5 finally sits on one page.
Part 1 · covers Chicago Booth AI in Finance 2026 (agentic + multimodal)

The agentic future, realistically 6 min live

The 2026 curricula have shifted. Leading programs now teach agentic systems - AI that plans and executes multi-step tasks - and multimodal AI that reads charts, documents, and tables together, as first-class finance topics. That is a real signal about direction. But the useful question for a CFO is narrower: over the next 24 months, what will finance agents actually do in your function, and what will they not do? The honest answer keeps your roadmap credible.

Now Literacy + quick wins policy, tool tiers 6 months Copilots on low-risk work first pilots run 12 months Copilots scaled agent pilots measured value 24 months Governed agents on bounded tasks Governed agents assist a bounded task - a human still owns the decision and sign-off.
🔍 Click to zoom - a 24-month strip: literacy and quick wins, then copilots, then governed agents on bounded work
LiveWhat finance agents will and will not do in 24 months3 min▶

An "agent" is AI that plans and carries out several steps toward a goal, not just a single reply. In finance, over a two-year horizon, the realistic scope is bounded and supervised - useful, not autonomous.

✗ Not in 24 months An autonomous CFO - no human signs off Trading or credit decided by AI alone Fails on governance, not capability ✓ Likely in 24 months Governed close assistant, human signs Forecast assistant surfaces scenarios Filings assistant answers, cited All three are bounded, with a person signing off - not an autonomous CFO deciding alone.
🔍 Click to zoom - bounded and supervised, not an autonomous CFO
  • Likely, and worth planning for. A governed close assistant that gathers, reconciles, and drafts variance commentary for a human to approve. A forecast assistant that pulls drivers, runs scenarios, and surfaces the ones worth a look. A filings assistant that reads a 10-K and answers grounded questions. All bounded, all with a person signing off.
  • Not in 24 months - and be clear about it. An autonomous CFO. AI that closes the books, files with regulators, or moves money without a human in the loop. Trading or credit decisions made and executed by the model alone. These fail on governance, model risk, and accountability - not just capability.
  • The dividing line. Agents shorten the path to a decision; the licensed human still makes and owns it. That line is where your a3 guardrails live, and it does not move just because the demo is impressive.
This section moves fast - re-verify Agentic and multimodal capability is the fastest-changing part of this course. Treat specific claims here as a snapshot, not a fixed truth. Before you present a roadmap, check the current state against a primary source; what is "not yet" today may shift, and your credibility depends on not overclaiming either way.
Self-studyMultimodal, in one paragraph2 min read▶

Multimodal AI reads more than text - a chart, a scanned invoice, a table, and a paragraph together, in one pass. For finance that means an assistant can look at a page of a board pack the way a human does, rather than needing everything pre-extracted into clean rows. It is genuinely useful for document-heavy work like filings review and invoice handling. It does not change the rails: the same privacy, sign-off, and audit-trail rules apply, and a confident read of a messy scan can still be wrong. Treat it as a capable reader that needs checking, not an oracle.

STRUCTURED: charts UNSTRUCTURED: scans charts, tables, invoices scans, prose, filings all at once Multimodal reads a chart, a scan, a table, and prose together in one pass - the same privacy and sign-off rails still apply.
🔍 Click to zoom - one pass over charts and prose together, same rails apply
Part 2 · covers AIFPA implementation, sequencing a portfolio

Sequencing the portfolio 6 min live

You have a portfolio of business cases from a5. The strategy is the order you run them in. There are three phases, and they are not optional stops you can skip - each one earns the right to the next. The most common way roadmaps fail is jumping straight to the exciting phase and discovering the foundation was never there.

LiveThree phases: foundation, adoption, transformation3 min▶

Read the table top to bottom - it is the order, not a menu. Value grows as you climb, but so does the cost of having skipped a rung.

PhaseWhat you doWhat it producesRough window
FoundationSet the AI-use policy, define tool tiers, run literacy across the team (a3 + a4)A team that can use AI safely, and rails everyone trustsNow - 6 months
AdoptionPut copilots on high-value, low-risk work; run the pilots from your a5 cases with baselines and decision gatesMeasured wins, real adoption, a credible track record6 - 12 months
TransformationMove proven copilots into governed agentic workflows on bounded tasks, human still signing offCompounding capability on the work that matters most12 - 24 months
Do not skip the foundation Skipping the foundation is why pilots fail. A team with no literacy will not adopt the tool; rails written after an incident are damage control, not governance. The foundation feels slow because it is not a demo - but it is the difference between a portfolio that compounds and one that stalls at "we ran a pilot once."
LiveWhy the order is the strategy2 min▶

The phases are not just chronological - each produces the thing the next one needs.

  • Foundation buys trust. Adoption only happens on rails people believe in and skills they actually have. Without it, the best tool sits unused.
  • Adoption buys credibility. A few measured wins - a close cut by two days, hours redeployed to analysis - are what earn you the mandate and budget to attempt agentic work. You cannot skip to transformation on a promise.
  • Transformation buys leverage. Only once a workflow is proven, adopted, and governed is it safe to let an agent run more of it. Automating a broken or unmeasured process just breaks it faster.
Real world

The team that jumped to phase three. A finance group, impressed by an agent demo, tried to automate the whole close before anyone had run a copilot or written an AI policy. The agent produced plausible-looking entries no one trusted, there was no baseline to prove value, and the auditors had questions no one could answer. They quietly shelved it and restarted with literacy and one small copilot pilot - the foundation they had skipped. A year of momentum lost to skipping two rungs.

★ Questions to ask your team Honestly, are we trying to skip to the exciting phase before the foundation is real? Which of our a5 cases is the right first pilot - painful, high-volume, low-risk? What has to be true - in policy, tools, and skills - before we let anything run more autonomously?
Part 3 · the artifact that carries the whole plan

The board narrative 4 min live

A board does not fund a use-case list; it backs a story it can repeat. The whole leader track collapses into five beats a board can follow in a few minutes - where we are, the bet, the guardrails, the milestones, and the ask. This is the a5 business case zoomed out from one use-case to the portfolio, and it belongs on a single slide.

LiveThe five beats of the story3 min▶

Tell it in this order. Each beat answers the question the board asks next.

  1. Where we are. The honest starting point, with a number. "59% of finance functions use some AI; we run two copilots today and have no shared policy." No hype, no shame - just the baseline.
  2. The bet. The direction and why now. "Nearly four in five CFOs plan to deploy generative AI within 24 months; we intend to lead our sector's adoption, not react to it." One sentence of ambition, grounded.
  3. The guardrails. The a3 rails, named up front. "AI assists, the licensed human decides. Privacy, sign-off, and audit trail on every use-case." A board trusts the leader who raises risk before being asked.
  4. The milestones. The three phases as a timeline with checkpoints. "Foundation by month six, two measured pilots by month twelve, first governed agentic workflow by month twenty-four - each with a decision gate."
  5. The ask. The specific decision you want today. Budget, a mandate, a named sponsor, the next review date. Make it easy to say yes.

Notice the shape: this is the a5 one-pager - problem, bet, cost/guardrails, value/milestones, ask - lifted from one use-case to the whole portfolio. If you can defend one business case, you can tell this story.

LiveOutline of the board slide2 min▶

One slide, five zones, read top to bottom in three minutes. Keep it to a page on purpose - if the story does not fit, the strategy is not finished.

  • Header - the bet. One line: where finance is going and our stance. This is the title, not a footnote.
  • Left - where we are. Two or three honest facts about today, with the market context number for scale.
  • Center - the roadmap. The now → 6 → 12 → 24 month strip with a theme per stage: literacy and quick wins, copilots, governed agents.
  • Under the roadmap - the guardrails. One line, always visible: "AI assists, the human decides - privacy, sign-off, audit on every case."
  • Bottom - the ask. The single decision, in bold. Budget, sponsor, next review date.
The one-slide test Hand the slide to someone outside finance and ask them to say the plan back to you. If they can - where we are, the bet, the rails, the milestones, the ask - it is board-ready. If they get lost, the problem is your story, not their attention.
Exercise

Sketch your 24-month roadmap ◐ 15 min · on paper

Pull together everything from a1 through a5 into one roadmap sketch and the bullets for one board slide. You are not building anything - you are proving the pieces connect into a story you could defend in the room where the budget lives.

★ Questions to ask your team If the board could back only the first six months, would our foundation phase still be the thing we protect? Which milestone are we least sure we can hit - and what would make us confident? Is our agentic ambition for month twenty-four honest given where the technology actually is, or is it a slide we would have to walk back?
Source material

Official sources covered

This finale teaches from a 2026 finance-AI curriculum and published implementation practice. Certificates, graded assessments, and paid tooling stay with the official programs - noted honestly. This session covers:

◐Chicago Booth - AI in Finance (2026 syllabus): agentic systems + multimodal AIPart 1 · agentic future; fast-moving - re-verify before you present
✓FP&A Professional Institute - AIFPA: implementation strategyParts 2-3 · phasing, sequencing, the board narrative
Check yourself

Three questions before you go 🎯 ◐ 90 seconds

1 · In a 24-month finance-AI roadmap, what must come first?

Foundation first: policy, tool tiers, and literacy. Skipping it is the most reliable way to make later pilots fail - a team with no skills will not adopt the tool, and rails written after an incident are damage control, not governance.

2 · What is a realistic scope for finance agents over the next 24 months?

In 24 months the honest scope is bounded and supervised: agents shorten the path to a decision, but the licensed human still makes and owns it. Autonomous decisions on the close, filings, credit, or trading fail on governance and accountability, not just capability.

3 · What does a board narrative need to do its job?

A board backs a story it can repeat, not a use-case list. The five beats - where we are, the bet, the guardrails named up front, the milestones, and a specific ask - are the a5 business case zoomed out to the portfolio, and they belong on one slide.

Leader session 6 cheat sheet · pin this

Strategy = sequence + storya pile of good use-cases is not a strategy. The order you run them in, plus the story you tell, is.
The 24-month stripnow → 6 → 12 → 24 months: literacy + quick wins → copilots → governed agents on bounded work.
Agents, realisticallygoverned close/forecast/filings assists, human signing off. Not an autonomous CFO. This moves fast - re-verify.
Three phasesfoundation (policy, tiers, literacy) → adoption (copilots on low-risk work) → transformation (governed agents).
Do not skip the foundationskipping it is why pilots fail. No literacy, no adoption; rails after an incident are damage control.
The five beatswhere we are · the bet · the guardrails · the milestones · the ask. Each beat answers the board's next question.
The one-slide testhand the board slide to an outsider. If they can say the plan back, it is board-ready.
Track finale → builder trackyou can lead the adoption now. Next, b1 - AI foundations for finance - starts the hands-on practitioner track.