The First
Six Months

A six month plan for the CFO role, built around getting the Series C done and putting the right operating discipline in place behind it.

PREPARED BY
Tim Weerasiri
PREPARED FOR
Jo and Monica
HORIZON
Sept 2026 to Mar 2027
SERIES C KICKS OFF SEPTEMBER 8  ·  THIS PLAN IS WRITTEN TO THAT CLOCK
01The argument

The business is stronger than the financials currently make it look.

Fixing that gap is the highest leverage thing Finance can do before the Series C.

01

The underlying business is already proving it

Employee Intelligence has gone from one customer to 28, we have lost none of them, and average contract value has tripled since the Series B. The financials do not make any of that obvious today.

02

The issue is structural, not an accounting clean up

A chart of accounts that does not separate what we sell, a history assembled from billing, and the largest variable cost uninstrumented.

03

I would attack it in three workstreams, in this order

Get the numbers investor ready before September 8, manage cash and the raise alongside that, then build the finance capability we need after the round.

EVERYTHING THAT FOLLOWS SUPPORTS THIS ONE STATEMENT
03The clock

The Series C sets the timeline, so the plan works backwards from September 8

This is not a normal onboarding. We need to compress the first few weeks around the raise.

SEPTEMBER 8

Now to Sept 8

Rebuild revenue from contracts and restructure the financial data model. Begin on contract ahead of the formal start if that helps accelerate timing.

September 8

The round starts. By then the key definitions are locked and the core diligence exhibits are ready.

Sept to Nov

Run a tight process toward a close around election day. Finance owns the numbers, the story behind them, and the diligence workload.

Nov to Mar

Then move into the audit, revenue policy, reporting and planning cadence. The goal is to operate like the company we just raised the money to become.

The compressing constraint

Kicking off the round will not wait for all financials to be ticked, tied, and rebuilt. That is why the revenue rebuild and the chart of accounts move in front of everything else, including the audit, so that we can tackle the highest leverage items first.

04Evidence

The business is performing better than the financials show

These are all numbers you shared with me. The issue is that an investor cannot see this story clearly in the financials today.

28
Customers on employee intelligence, up from one customer, fifteen months ago
Zero
Customers lost since the product launched, on any line
3x
Growth in average contract value since the Series B
26%
Win rate from qualified opportunity, mostly through enterprise RFPs
The pattern

Customers are expanding, not just renewing

Every customer on the line has bought more, other than the one still working through its pilot rollout. One three thousand person account went from a first deal to over a million dollars inside a single quarter.

The constraint

The bigger constraint looks like capacity, not demand

Eleven million in late stage pipeline is carried by four sellers with no marketing function behind them, against a mid market motion with a one to two month cycle that is barely explored.

THIS IS THE FUNDABLE STORY  ·  THE PLAN EXISTS SO THE STATEMENTS TELL IT PLAINLY
05Why it matters

The biggest thing we can control before the round is the quality of the financial story

The market

Rates, comparable multiples and investor appetite for application layer AI. We do not control those.

The product story

The product story is already strong and the team knows how to tell it. I would not spend much time trying to reinvent it.

The numbers

This is in our control, it currently understates the business, and we can materially improve it before the raise.

Why this matters to value

These workstreams can have a direct impact on how the business is valued

At any revenue multiple, every million of ARR correctly stated is that multiple in enterprise value.

06Root cause

The issue is structural, not an accounting clean up

There are three underlying design problems. A faster close or a better controller does not solve them.

01
Schema

The chart of accounts does not separate what the business actually sells

The chart of accounts is the data model for the financial statements, without correcting this layer, inputs are slow and cumbersome to get correct, and outputs do not make sense.

02
Basis

Revenue history was assembled from billing events rather than from contracts

Quarterly ARR moves down in a business that has never lost a customer. That is a recognition artefact and a billing lag, not a demand signal, but the statements cannot currently say so.

03
Measurement

The largest variable cost in the business is not instrumented

Model spend is not attributed by customer, environment or agent, and the ceiling can be pushed through. Gross margin therefore cannot be defended line by line.

ALL THREE ARE DESIGN DECISIONS TAKEN ONCE  ·  NONE OF THEM RECUR
07The structure

I would attack it in three workstreams, in this order

The September 8 deadline drives the order: get the numbers credible first, manage capital in parallel, then build the longer term finance capability.

C1

Credibility

Numbers we can stand behind
GATED BY SEPT 8
  • Financial data model rebuilt
  • Revenue rebuilt from contracts
  • Metric definitions fixed once
  • One reconciliation exhibit
  • Lineage and compliance register
  • Diligence risks surfaced first
C2

Capital

Cash through to the close
CONTINUOUS
  • Debt draw closed cleanly
  • 13 week cash flow, weekly
  • Collections and billing policy
  • Related party governance
  • Inference spend measured and capped
C3

Capability

Build the finance function we need afterwards
AFTER THE CLOSE
  • Audit and revenue policy
  • Reporting and BI layer
  • Planning and forecast cadence
  • Capacity and quota model
  • Outcome based pricing
  • Finance org design
SEQUENCE
SEPT 8
AUGSEPTOCTNOVDECJANFEBMAR
C1
Workstream one  ·  gated by September 8

Credibility

The round gets harder if investors do not trust the numbers. So the first job is to get the financial model, revenue history and metric definitions to a place we can stand behind before September 8.

The chart of accounts as data model
Revenue rebuilt from contracts
Contracted revenue as the headline
One reconciliation exhibit
Lineage and compliance register
Surface the diligence risks ourselves
08Credibility

The chart of accounts is finance infrastructure, not bookkeeping

If the underlying structure is wrong, the inputs are more difficult slowing information readiness and the output is funky anyway. Fix the structure once.

Why the numbers do not land

The problem is how the data is structured

The numbers are not telling the story because, amongst other things, the accounts do not distinguish subscription from consumption from delivery.

Better commentary will not fix that. Changing the chart of accounts – the financial data model - underneath will.

What gets designed

Three dimensions I would build into the model

Revenue by product line and by revenue type, so subscription, agent consumption and true services never touch again.

COGS broken out with inference spend as its own account, so gross margin is real.

A department dimension, so the research versus go to market split is an easy query

Timing

Historically a six-to-twelve-week exercise. Using AI to accelerate mapping and reclassifying can compress the timeline effectively. A full mapping table from old model to new needs to be retained, so history restates cleanly and the change is auditable.

09Credibility

Use the contracts as the source of truth, not the invoices

Build one structured contract dataset and use it to drive every revenue view we publish.

Extraction schema

What we capture from every contract

Parties, effective date, term, total contract value, billing schedule, ramp, escalators, renewal terms, and any go live or acceptance gate.

Four outputs, one source

One dataset, multiple outputs

Contracted ARR. GAAP revenue under 606. The deferred position. And the reconciliation between them. Today those are three separate exercises that disagree with each other.

The control layer

How we make it defensible

We don't have so many contracts that tying the contract summaries back to the schedule is impossible. This will hold up to diligence and subsequent audit.

10Credibility

Lead with contracted revenue, and define it once

GAAP revenue matters, but it is likely not the best way to show growth in this business. I would show both, with contracted revenue as the lead metric and a written definition that does not move during the process.

Lead with contracted revenue

Defined once, published in the room, never adjusted mid process. One number the board, the model and the market all read the same way.

Do not stretch the ARR definition

Agent usage counts only where a contracted minimum sits under it. Everything else is shown separately as upside. Fold it in and diligence strips it out, possibly costing credibility.

Show contracted value alongside ARR

Total contracted value and remaining performance obligation. Multi year deals with ramps make bookings momentum invisible in a quarterly ARR line, which is an issue I think we have today.

Make NRR a headline metric

No churn since inception and near universal expansion should produce the best single statistic in the business and possibly in the market. It’s possibly so strong it could look ridiculous. It currently appears nowhere.

INVESTORS FORGIVE AN UGLY NUMBER  ·  THEY DO NOT FORGIVE A DEFINITION THAT MOVED
11Credibility

One simple bridge makes the revenue history make sense

Four columns, tied out for every period, available from day one of diligence.

CONTRACTED

What customers have committed to, from the contract schedule.

BILLED

What has been invoiced, under the new policy and its effective date.

RECOGNISED

What 606 allows in the period, including the deferred position.

COLLECTED

What has landed in the bank, tied to the balance sheet.

Without the bridge, a billing timing issue can look like a demand problem or even worse – like churn

Every awkward question about the historical revenue line resolves once the four columns sit beside each other. The same facts then read as a billing discipline issue that has already been fixed, with a date attached to the fix. This exhibit is also what lets us lead with contracted revenue without anyone suspecting the GAAP number is being avoided.

12Credibility

Get the data rights work done before diligence starts

The whole asset is a graph assembled from public and partnered sources. Lineage means proving, for any field, where it came from and under what right.

FCRA

Once output drives hire, fire and promote decisions there is an argument the data is a consumer report. Prospect legal teams are already asking.

GDPR

European residents processed without consent needs a documented legitimate interest test, plus erasure and objection handling against a graph.

EU AI Act

Employment related AI is classified high risk, carrying conformity, documentation and human oversight obligations.

US patchwork

New York City bias audit rules, Colorado, and the California automated decisionmaking regulations.

Adverse impact

Inferred proficiency is heading toward promotion, succession and a skills based pay foundation. That needs testing.

Provenance

Collection methods viable in 2017 may not be viable now, and the terms behind historical data may have changed since.

Diligence Readiness

Built with counsel and complete before the room opens. This is the sort of thing that stalls rounds when it surfaces late and could also be a lever inside nine-month enterprise cycles.

13Credibility

Couple of housekeeping things we should be prepped for

These questions are likely to come up anyway. If we address them first, we control the discussion and build credibility.

Priority one

Pressure test the Verizon case study

The eighty two percent reduction in unwanted attrition is at once our strongest asset and our largest diligence risk. It is an extraordinary result for a single intervention across a seventy five thousand person workforce, where attrition is normally driven by pay, management quality and the labour market.

What I would establish in September: the baseline, the denominator, whether it is a cohort or the full population, and what else changed in that period. Same treatment for the twenty nine million in operating savings, separating hard cash from imputed employee time.

If it holds, we lead with it. If it does not hold as stated, we need to know in September rather than during dilligence.

Receivables timing

A large share of the balance invoiced in one month immediately ahead of a raise reads as a pull forward. Answer it with a dated policy change and a collections curve.

Revenue concentration

Twenty eight customers with one anchor logo carrying the case study. Name it, show the cohort expansion behind it, show the mid market pipeline that dilutes it.

Capacity as the ask

A twenty six percent win rate and eleven million in late stage pipeline carried by four sellers and no marketing. Built by segment, that is the use of proceeds argument rather than a gap.

C2
Workstream two  ·  runs continuously

Capital

Keep enough cash in the business to get the round closed, and put proper ownership around the decisions that matter.

The draw closed cleanly
13 week cash flow, published weekly
Collections and billing policy
Related party debt governance
Inference spend measured and capped
14Capital

Get the draw closed and stay on top of collections

The immediate job is simple: make sure we have enough liquidity to run the process properly.

01

Get the draw closed

Resolve the backstop letter or move to the bank facility. Take more capacity than the immediate need where terms allow, since it can be repaid from round proceeds.

02

Run a 13 week cash flow

Built in week one, published weekly, and the format does not change. This is the single artefact that answers the predictability question fastest.

03

Collections

The receivables pattern reads as a pull forward unless it is collected and unless the new billing policy is documented with an effective date.

15Capital

Measure model spend before we try to defend gross margin

Model spend is part of cost of revenue. Today I’m not sure we can properly attribute it and we do not have a hard cap around it.

Measure

Get to a monthly number we can defend

Spend broken down by environment, by customer and by agent. A single invoice total cannot tell us whether an account is profitable or whether an internal experiment is quietly expensive.

Cap

Put a real cap around it

The limiter is soft today and a handful of people can push through it. That is an uncapped cash exposure with no owner. A real ceiling plus a documented route to raise it takes days, not weeks.

Why this matters for the raise

From what I’ve seen gross margin is where this market currently separates infrastructure from resold intelligence. If COGS cannot be defined precisely, covering hosting, inference, data acquisition and delivery, then the margin profile that justifies the multiple cannot be defended. Getting the definition right is worth more in the room than any operating saving it produces.

C3
Workstream three  ·  after the close

Capability

Once the round closes, the job changes from proving the story to running the business better. This is the work that should make the next raise much easier.

Audit and revenue recognition policy
Reporting and BI layer
Planning and forecast cadence
Capacity and quota model
Outcome based pricing framework
The board pack, rebuilt
16Capability

Build the operating discipline that makes the next raise easier

Over months four to six I would put six core pieces in place. Each one should remove a recurring surprise or a recurring debate.

Audit and revenue policy

Audit kicked off against a clean finance data model, a documented ASC 606 policy, and numbers we feel good presenting.

The reporting layer

Warehouse plus semantic layer, ingesting CRM, product usage and billing. This gives us operational dashboards for faster decisioning.

Planning cadence

Monthly close on a published date, a rolling forecast, and quarterly planning that produces owned commitments.

Capacity and quota model

What the go to market build actually buys, modelled by segment, so hiring against the round is a calculation rather than a bet.

Outcome based pricing

The framework for the agents. Jo raised it first and it is the highest leverage margin lever in the business. This might be more ongoing effort.

Finance org design

What we build internally and what stays outsourced, decided deliberately rather than by drift.

THE RESEARCH TO GO TO MARKET SPLIT MOVES FROM ROUGHLY 70/30 TOWARD 50/50 ACROSS THIS BLOCK
17Capability

Build the board meeting around strategic decisions, not show and tell

The board should spend its time debating a few things that matter a lot, not listening to us present a pack. The format should guide that.

01

Put the decision agenda up front

The three or four things we actually need from this board, written as decisions rather than as updates.

02

Give the board the facts before the discussion

A board pack goes out early containing the facts a director needs to form a view, so discussion starts from a shared base of understanding rather than from questions.

03

Every ask leaves with an owner

Named introductions, specific asks, owners and dates.

04

Keep the detail in the appendix

Financials, metrics and the key reports available in full, but not read aloud.

Assume every director puts the pack through an AI tool before the meeting. Write it so the summary they get is the summary we want them to have.

18Accountability

Six things I am committing to

Do the highest leverage work first, and be explicit about what I need from the team.

Commitments, with dependencies
1

Restated revenue history from contracts

Before the round kicks off  ·  I need contract and billing access early

2

Rebuilt chart of accounts, history mapped

This is the underlying data model for finance. Within one week of start  ·  I may need outsourced capacity here

3

13 week cash flow, published weekly

From week three – chart of accounts dependant

4

Metric definitions and the bridge exhibit

Before the room opens  ·  needs agreement that definitions are then fixed

5

Data rights and compliance register

Before the room opens  ·  likely needs counsel engaged in September

6

Board pack in the new format

Second board cycle after start  ·  no dependency

19Accountability

Predictability comes from cadence

The goal is that neither of you should have to chase me for status. The cadence should make it obvious.

Weekly

Cash and pipeline

13 week cash flow, collections position, late stage pipeline movement. Same format every week.

Weekly

A short written update

What moved, what slipped and why, and what I need from you. Keep it to roughly 200 words instead of adding another meeting.

Monthly

Close on the same date every month

Set the close date in advance and hold it. If we miss it, that is useful information in itself.

Monthly

The metric pack

Contracted ARR, retention, the bridge, gross margin including inference. Same definitions every month.

Quarterly

Board pack and decisions

Decision agenda up front, homework out the door, the full pack available behind it.

Always on

A visible scoreboard

Every commitment in this plan should have an owner, a date and a status that anyone can see without asking.

20Close

What I need from you, and what success looks like

What I need from you
  • Contract files and read access to billing before day one, on a contract basis ahead of the start date if that helps.
  • Counsel engaged on the data rights review
  • Agreement that the metric definitions are set once and do not move while the room is open.
  • A defined handover window with the outgoing CFO
  • An Offer Letter
What good looks like in six months
  • A Series C closed on numbers we were confident in from day one.
  • A financial data model that makes the close faster and reporting straightforward.
  • One set of metrics used consistently by management, the board and investors.
  • Gross margin we can defend, including the real cost of model usage.
  • A forecast model we can rely on for decisions
  • And that feeling where you can’t remember the CFO not working here
TIM WEERASIRI  ·  PREPARED FOR CENSIA AI  ·  AUGUST 2026
← → TO NAVIGATE  ·  N FOR NOTES
Speaker notes