LIVECEO FOR PRIVATE EQUITY · EXPERIENCE PLAN · V2
Proposal — nothing rebuilt yet 2026-08-25 Part 2 of the document family

Attention over navigation.

v1 proved the intelligence: one canonical data model, a source for every claim, killer scenes that land. It also proved the wrong shell — 9 nav items, ~40 views, 80+ widgets. v2 keeps the brain and kills the CRM: two surfaces, one composer, screens that come to you.

How to read this: it is a proposal to challenge together, not a spec. Every recommendation is marked, and fourteen open questions at the end are where the brainstorm starts.
LiveCEOMR
MONDAY, AUGUST 24
One thing is urgent,
three need you this week.
$212M REV · $31.4M EBITDA · 1 RED · 2 AMBER · 2 GREEN
Northlane · Covenant6:58 AM
60+ day delinquency crossed the covenant threshold: 4.2% vs 3.5%.
credit-book datasetq2-credit-policy-review
Portside · Meeting Thu 10:00in 3 days
Atlas Freight exec meeting — prep pack ready. $820K, 45 days stalled.
Portside and Meridian are on plan. 12 more signals watched, none urgent.
Ask the portfolio anything…⌘K
WHERE V1 FALLS SHORT

A great brain in a CRM's body.

Credit first: v1 proved the hard parts. One canonical data model keeps every number consistent everywhere — the 4.2% delinquency, the $820K Atlas Freight deal, the 9-day launch buffer appear identically in cards, tables, and chat. Every assistant answer ships source chips. The killer scenes exist and land. Nothing below argues with that content. All of it argues with where the content lives.

v1 — Portfolio overview
v1 home screen: left navigation, dashboard widgets, assistant rail

4 nav sections + 5 company pages + a sidebar assistant = a CRM in the making. Roughly 12 interactive targets in the chrome before any content renders. The assistant — the only surface that answers cross-cutting questions in one step — gets a 320px rail, visually the twelfth thing on screen, and collapses to a floating button on a laptop.

v1 — Northlane Financial
v1 company workspace with seven tabs

Seven tabs per company, five companies: 35 views. "Is Northlane on plan?" lives behind tab four, Alignment — if you already know that. Nothing in the UI tells you. At 20 portfolio companies this becomes 140 tab-views.

v1 — Watchtower
v1 Watchtower alerts destination page

A destination page for your own warnings. A crossed covenant threshold and a competitor's tent-price change get the same row, the same type size, the same Acknowledge button. The user visits their alerts; the alerts should visit the user.

"Is Northlane actually on plan?"
Sidebar → Northlane (1) → guess the right tab among seven → Alignment (2) → scan five panels (3).
2 clicks + a scan — if you already know where plan-vs-actual lives
"Which company is most exposed right now?"
No view ranks exposure. The navigation answer: open five company pages and mentally join their risk panels — 5+ clicks across 35 candidate tabs.
The assistant answers in one: Solstice — TrailMart at 34% of revenue
"What changed since Friday?"
Three items in the home briefing card, four alerts on Watchtower, per-company signals in the portfolio table. Three screens to assemble one delta.
No navigational home at all — and ⌘K can't find it either
"The interface asks you to find the problem. The product's promise is that the problem finds you."
FAULT 01

Navigation-first: you must already know where to look

~40 distinct views, 80+ widgets, ~25 dead-but-live-looking buttons — around 43 honest places an answer could live. Every scripted demo question is one click in the assistant and 2+ clicks plus a scan through navigation. The IA taxes exactly the questions the product exists to answer: the cross-cutting ones.

FAULT 02

The assistant is an accessory bolted onto dashboards

~1,100 lines of dashboard components against 149 lines of assistant panel. Voice is a 1.7-second timer that fakes listening. Citation chips open nothing. The single most on-thesis button — Dealflow's "Ask across the vault" — has no onClick. The layout says: dashboard product, assistant attached. The thesis demands the reverse.

FAULT 03

Everything is equally loud

The Northlane covenant breach — the most consequential fact in the portfolio — renders six times across the app, and not one placement ranks it above anything else on its screen. The interface presents; the user triages. Attention ranking — the product's actual job — happens entirely in the partner's head.

FAULT 04

Proactivity is trapped in one widget

"Since Friday, updated 8:02 AM" — the demo's best idea — is one card among ten, competing for the same glance as an opex chart. "Read briefing," "Open full briefing," "Voice readout: Ready," "Preview tomorrow's briefing" — all dead. The brief should be the home, not widget number seven on it.

FAULT 05

Every feature costs a permanent screen

Dealflow became a sixth nav area, alerts became a page, tasks became a kanban plus an Operations page, competitor intel became a tab. Add LP reporting, fund admin, 20 companies, 18 integrations — the nav scrolls, the tabs wrap, and ⌘K becomes survival gear. The fix is a pricing change: a new capability must cost near-zero screens.

FAULT 06

One fixed layout for three incompatible jobs

The analyst needs depth on demand. The partner needs five ranked bullets before IC. The portfolio-company CEO — the persona in the owner's brief who installs the product and feeds data upward — has no surface at all. All get the same nine nav items. Only a surface that composes itself to the person and the moment can serve them.

"Every feature currently costs a permanent screen. At twenty portfolio companies, that pricing model buys you Salesforce with better typography."
PRINCIPLES

Six rules the v2 experience obeys.

Each one is testable against any future feature request. If a proposed capability breaks a rule, the capability changes shape — not the rule.

01

Attention over navigation

The product ranks; the user decides. Opening the app shows an opinion about where your attention goes right now — never an inventory. If it isn't ranked, it isn't shown.

02

The conversation is the interface

Typed, spoken, or tapped — every intent routes through one answer pipeline. There is nothing the UI can do that asking can't, and nothing asking does that the UI contradicts.

03

Screens are summoned, not visited

No destinations. Every dashboard, table, and prep pack is a composition that materializes when it's needed and dismisses when it's done. A new capability costs a new answer, not a new nav item.

04

Proactive by default

The brief is the home. One ritual surface plus a hard budget of high-precision pushes (≤3–5/day — the researched attention ceiling). Nothing else interrupts; overflow queues for tomorrow's brief.

05

Persistence must be earned

Compositions are ephemeral by default. The only persistence path is explicit — "Pin as live" — and a pin becomes a summonable surface refreshed on every reindex, never a nav destination. No badges, no unread counts, no archives.

06

Every claim cited, every pixel real

A card without citations cannot render. Chips open the actual source page. No dead buttons, no fake mics, no decorative affordances: if it renders, it works.

THE EXPERIENCE

Two surfaces, no more.

The assistant is the application. Screens are answers. There are exactly two surfaces — and only one of them is ever "the screen you're on": Today, a ranked attention stream, and the Canvas, a near-blank stage where asking materializes rich surfaces. No left nav. No tabs. No company pages. Everything the old 40 views showed still exists — as summonable compositions.

SURFACE 1 · TODAY — THE RESTING STATE
LiveCEOMR
MONDAY, AUGUST 24
One thing is urgent, three need you this week.
$212M REV · $31.4M EBITDA · 1 RED · 2 AMBER · 2 GREEN
Northlane · Covenant6:58 AM
60+ day delinquency crossed the covenant threshold: 4.2% vs 3.5%.
Driven by the Q2-2026 manufacturing cohort; the credit memo flagged drift in July.
credit-book datasetq2-credit-policy-review
OpenDelegateLater
Portside · Meeting Thu 10:00⏱ in 3 days
Atlas Freight exec meeting — prep pack ready.
$820K committed deal, 45 days stalled; champion quiet; leadership change at the prospect.
prep packaccount pageemail thread
Open prepRead it to me ThuLater
Vortex · Commitment at risk
"Cert-ready by Oct 1" vs QA queue math — 9-day buffer left.
board call 08-12jira dump
Approvals · 1 pending
Covenant letter section drafted — review & approve.
Portside and Meridian are on plan. 12 more signals watched, none urgent.
Ask the portfolio anything…⌘K

A ritual brief, not a feed. A dated headline written by the same agent turn that assembles the brief; one mono pulse line (tap it to summon the full portfolio composition); a hard cap of 7 ranked cards; a quiet line that makes absence a claim, not a gap. Cards die: resolved · handled · expired · dismissed. Today never accumulates.

Banned from TodayMetric-card walls, tables, charts, company tiles, task columns, unread badges, "view all" links. Claims and evidence, never inventories.
Every card is a promiseExpanding never dead-ends — it materializes the full surface on the Canvas with the evidence already attached. Actions: Open · Delegate · Later.
One chrome bar, totalWordmark + avatar. No sidebar, no bell, no workspace switcher. The composer and mic are fixed at the bottom in every state.
SURFACE 2 · CANVAS — THE STAGE IN FOCUS
LiveCEOMon Aug 24 — 1 urgentMR
Northlane — Covenant Watch

The spike concentrates in the Q2-2026 manufacturing origination cohort — it drives most of the increase. The July credit-policy memo flagged underwriting-model drift before the print q2-credit-policy-review. Covenant disclosure is due to the lender within 30 days facility agreement §7.2.

trend-chart · 60+ day delinquency vs 3.5% covenant
3.5% covenant 4.2%
kpi-row
60+ delinq
4.2%
Loan book
$118M
Disclosure due
30d
doc-excerpt · credit-committee memo, Jul 14

"Approval-rate drift in the manufacturing vertical suggests the underwriting model is mis-scoring seasonal cash-flow risk."

entities/decisions/q2-credit-policy-review
cohort-table · originations by quarter, 60+ delinquency
CohortBalance60+ ratevs book
Q4-2025 · all verticals$24.1M2.6%−1.6pt
Q2-2026 · manufacturing$18.7M8.1%+3.9pt
Q2-2026 · all verticals$31.2M5.9%+1.7pt
Book average$118M4.2%
Delegate taskPin as liveShareMake a document
Generated 7:49 · every figure traces to a governed query · composition #c-2081
Why did it spike?⌘K

Asking makes surfaces materialize. The agent emits a typed composition; a deterministic renderer mounts real blocks with a ~120ms stagger, so the answer visibly assembles. A follow-up amends the composition — the stage holds one subject at a time; prior turns collapse into the thread rail. Citation pills open the source in a reader overlay. With nothing pending, the stage is near-blank — “Ask the portfolio anything” plus three suggestion chips. On a normal morning, though, the resting state is Today’s ranked brief — whether the home should instead rest blank is Q13.

One screen, two statesToday is the Canvas at rest. Any act of intent folds the card stack into the top ribbon (one dot per card + the date summary); Esc unfolds it back. Tabs are the first CRM cell division — so there are none.
What never persistsCompositions clear when focus ends. History is retrievable by asking ("show me Friday's Northlane view"). Only "Pin as live" persists — summonable, reindex-refreshed, never a destination.
Nothing auto-appliesEvery write the assistant proposes — task, letter draft, status change — lands in the Proposal Inbox as a cited diff for human approval. Propose-only is the consent model, unchanged from production.

Monday, 7:42 — Maya opens LiveCEO

7:42

No dashboard. No sidebar. A quiet page: "Monday, August 24 — one thing is urgent, three need you this week." Under it, the pulse line. Four cards, ranked. The top card has a red rail: NORTHLANE · COVENANT — 4.2% against 3.5%, two source chips. It pushed to her phone at 6:58; here it waits with everything attached.

7:43

She taps it. The stack folds into a slim ribbon; blocks assemble in under a second — the delinquency trend with the threshold breached, a cohort table isolating Q2-2026 manufacturing originations, the credit-committee memo that flagged drift before the spike. Every number carries a citation pill.

7:45

She types: "Why did it spike?" Three sentences stream in: the manufacturing cohort drives it; the memo predicted it; disclosure is due to the lender in 30 days. Cited.

7:47

The kettle boils. She taps the mic. "What should I ask Northlane's management first?" The assistant speaks — three questions, no numbers read aloud — while the written, cited version lands beside the cohort table.

7:48

"Draft the covenant disclosure section for the board letter. Put it in front of me — don't send anything.""Drafting. It'll be in your approvals with sources." A propose-only task is created. Nothing auto-applies.

7:49

Esc. The ribbon unfolds into Today. The Northlane card now reads "Briefed 7:49 · draft pending your approval." Second card: Atlas Freight, Thursday 10:00 — $820K, 45 days stalled, champion quiet, prep pack ready. She says: "Read me this prep on Thursday when I'm driving in." Scheduled.

7:50

Third card, amber: Vortex's cert QA queue grew a third straight sprint — nine days of buffer against the board's "cert-ready by October 1." She leaves it for the partner call. Below: "Portside and Meridian are on plan. Nothing else needs you."

7:51. She closes the laptop. She has not clicked a navigation item once. There aren't any.
HOW SCREENS MATERIALIZE

Three models. One clear pick.

How does asking become interface? The 2025–26 production landscape gives three candidates — and a market verdict on each.

A — Summoned pre-generated surfaces B — Fully generative UI C — Composition over a vetted block libraryRecommended
Mechanism Finite set of hand-designed surfaces; an intent router picks one and fills slots; instances pre-generated ahead of need. Model streams bespoke layout or code per answer (Thesys C1 / make-real style). Model emits a typed JSON composition — which blocks, what order, bound to which governed metrics; a deterministic renderer mounts real components.
Wow Medium — the magic is anticipation ("prep card already made"), not novelty. Highest — "the software builds itself." High — visibly generative assembly, always crisp.
Trust Highest; same surface every time, spatial memory builds. Lowest — layout chaos; can't tell insight from rendering bug. Disqualifying for finance. High — every pixel from a reviewed component, every number from the governed lane; variation only in arrangement, the safe axis.
Cost Lowest, bounded. Fully snapshot-testable. Deceptively high: weekend prototype, unbounded hardening; effectively untestable. Medium; the block library, schema, and renderer are durable assets — snapshot-testable per block, compositions loggable and replayable.
Market verdict Perplexity / Granola / Raycast pattern — ships everywhere. Vercel paused AI SDK RSC and marks streamUI experimental — the best-resourced team stepped back. Where 2025–26 production converged: AG-UI, Google A2UI, MCP Apps, assistant-ui JSON spec, CopilotKit Gen-2.
FOR THE DEMO

Model A content in Model C's skeleton

Build the composition schema and the deterministic block renderer now, but ship the demo with pre-generated compositions — hand-authored JSON for every killer scene and every Today card, summoned by an upgraded intent router (v1's /api/ask keyword chain, promoted to intent → composition-id + slot fill). The renderer stages block arrival so materialization reads as assembly. Honest about what the demo is — v1 is already 8 canned answers — and nothing is throwaway: each hand-authored composition becomes a golden-set eval for the live model later.

FOR THE PRODUCT

Model C live, on existing rails

The agent turn gains one write tool, render_composition, emitting the typed JSON — the exact event-intercept pattern already used by the alert and task tools. Charts never draw from prose: every numeric block binds to a SELECT-only, AST-validated dataset query, and the post-turn numeric-claims verifier already checks that figures trace to that turn's results. Ritual surfaces (morning brief, meeting prep) are saved compositions in the same grammar, refreshed by the post-reindex hooks — Model A and C are one system. The LLM-HTML artifact pipeline is demoted to documents only; open code-gen stays quarantined where its failure mode is a typo, not a wrong covenant number.

The block library, v1 (~18 blocks), reuses v1's proven renderers: kpi-row · trend-chart · bar-compare · cohort-table · pnl-table · risk-flag · commitment-card · person-card · meeting-prep · doc-excerpt · proposal-diff · task-strip · deal-card · graph-snippet · timeline · briefing-list · narrative · action-strip. Compact variants of the same blocks render Today cards — one grammar, two densities.

THE PROACTIVITY ENGINE

What fills Today — and what powers it.

One rule governs the engine: the tick, not the event. Every trigger class is a durable-state sweep on LiveCEO's existing heartbeat — the post-reindex hook chain plus the every-minute scheduled-job clock — running a headless agent turn and producing a cited, propose-only card. A PE Jarvis is new sweep recipes over existing rails, not new infrastructure. A card without citations cannot render.

Trigger classExample Today cardPowered by (real LiveCEO block)
01Capital & compliance thresholds "Northlane 60+ day delinquency 4.2% vs 3.5% covenant" · "Meridian CLIA recert: 47 days" Standing NL alerts created by asking (create_alertalertEval.ts), each re-evaluated by its own headless turn after every reindex; thresholds computed via the datasets lane.
02Calendar horizon "Atlas Freight exec meeting Thu 10:00 — prep pack ready" calendar_events system dataset + the T−30 pre-meeting brief generator (meetingBrief.ts: attendees, what each owes, what changed) emitting a meeting-prep composition.
03Commitments made in meetings "Vortex board committed 'cert-ready by Oct 1' — QA queue math now contradicts it" T+10 post-meeting extraction (meetingExtract.ts) writes commitments; the Status Truth Engine + dependency-slip radar (taskSweepCore.ts) detect drift.
04Anomaly / delta detection "Portside NRR 118% → 109% year over year" · "Since Friday: 3 changes" Scheduled jobs running SELECT queries over portco KPI datasets on their own cron; the numeric-claims verifier guarantees the figure traces to the query.
05Staleness & silence "No Northlane management report in 6 weeks — longest gap this year" Wiki stale_after frontmatter flags + the evidence-based stale-nudge sweep (taskSweeps.ts).
06Web signals "Solstice competitor raised tent prices ~8% in DACH; review score slid" Daily web-signals sweep via the Perplexity lane writing raw/web/ dumps; answers carry the production "part of this answer came from the internet" notice.
07Pending approvals "2 drafts awaiting your approval: covenant letter section, Solstice counter-move task" The Proposal Inbox (taskProposalApply.ts) — the propose-only lane surfacing as exactly one card, never as a badge on chrome.
RANKING — DETERMINISTIC, EXPLAINABLE

Five tiers, hard cap of 7 cards

Tier 0 capital at risk (covenants, compliance <45 days) — always first, never dialable. Tier 1 imminent time (meetings <24h, commitments due). Tier 2 trajectory breaks. Tier 3 deltas since last open. Tier 4 hygiene. Within a tier: magnitude, then recency. Overflow folds into the quiet line. Scores are logged per card, so "why is this first?" is itself an askable question.

THE ATTENTION DIAL — ONE USER CONTROL

Quiet · Standard · Vigilant

The dial governs push (Slack DM, Telegram, email — all existing channels), never what Today shows. Quiet: Tier 0 only. Standard (default): Tiers 0–1, ≤3 pushes/day. Vigilant: Tiers 0–2, ≤5/day. The ceiling comes from the attention research — 3–5 meaningful notifications per day across all sources, ~23 minutes of refocus cost per interruption. Excess candidates queue for the next morning's brief.

PERSONAS

Four people, one brain, four different mornings.

v1 shipped one implicit persona and 40 views. A Jarvis product is defined by moments, not screens: something happens in the data, the assistant acts, one surface materializes, the person decides. Everyone gets the same two surfaces — scoped, ranked, and worded for their job. Names beyond Maya are proposals.

MR

Maya Reynolds — Investment Partner

Northstar Capital, Fund III · sits on three of the five boards

Her day is sliced into meetings: Monday partner call, board calls, LP conversations, IC. She doesn't explore data; she consumes synthesis and makes calls. Her worst failure mode is being surprised — by a covenant, an LP question, or something management didn't flag.

Monday 7:55 · Partner call

The overnight sweep has compiled "Since Friday": Northlane's covenant-letter draft is ready; Portside's stalled $820K deal finally has a Thursday meeting; a Solstice competitor launched 20%-off in Germany over the weekend. The brief is the opening screen — three cited lines, one-tap voice readout.Partner-call prep: ~30 minutes of tab-hopping → 90 seconds.

Covenant breach lands

Before she asks "why," a headless turn has segmented the loan book by cohort, isolated Q2-2026 manufacturing, and pulled the memo that predicted the drift. Two proposed actions wait in her approvals — nothing auto-sent.Risk caught the day the data lands, not in the quarterly pack — with the "why" attached.

T−30 · Vortex board call

A prep card materializes: attendees, what each owes, what changed — and the hard question. Management committed "cert-ready by October 1"; the QA queue math now contradicts it, and none of it appeared in the board deck.She walks in with the question management hoped nobody would ask.

Mid-call · LP curveball

"Where is your concentration risk?" One agent turn ranks all five companies — Solstice at ~34% of revenue in TrailMart, Portside healthiest at 6% — with citations and the first question to put to Solstice management.An LP-grade, cited answer in seconds instead of "we'll follow up."

Before 9 a.m. her screen shows: the Monday brief (3 cited lines), one red exception with analysis attached, one prep card for the 10:00 board call, and a composer. Four things. Nothing else.
Kept out of her view: 7-tab workspaces, kanban boards, deal tables, P&L grids, alert-rule builders, raw transcripts. She can summon any of it by asking — she never navigates to it.
DO

Daniel Okafor — Investment Associate

Covers Northlane and Portside plus the dealflow funnel

The power user: builds board packs and IC memos, answers partner asks within the hour, screens inbound decks. The current CRM shape punishes him most — he's the one who knows which of 7 tabs holds each answer, which is precisely the knowledge the product should make worthless.

Maya forwards: "Why?"

Cohort segmentation through the datasets lane; the answer traces to Q2-2026 manufacturing with citations into the credit-policy memo and the board-deck dump; every figure verified. He forwards the composition itself.An afternoon of loan-tape Excel becomes one question — with an audit trail Maya can click.

New deck lands in Drive

"Have we seen this pitch before?" Three past logistics-marketplace deals surface: deck claims side by side, the take-rate pushbacks, two pass memos — and a flag that one founder is raising again with a pivoted deck. This is v1's dead "Ask across the vault" button made the entire dealflow experience.Institutional memory in one question. Pass memos finally compound.

Maya challenges a number

Every figure traces: citation pills open the reader panel onto the actual wiki page; dataset answers expose the executed SQL. Verification without a CRM tree — provenance is the only "navigation" in the product.v1's non-clickable chips were the most corrosive fake. Fixed by construction.

Before 9 a.m.: overnight triage of two new inbound decks scored against pass-memo history, the Northlane cohort cut pre-computed on the covenant card, suggested questions queued for the 10:00 IC.
Kept out of his view: companies outside his coverage (access-scoped), the partner's LP correspondence, CEO-side operational chatter beyond the governed upward view.
PS

Priya Sharma — Operating Partner

Works across all five companies on execution

Lives in the delta between the board-approved plan and operational reality: hiring, pricing, channel mix, 100-day plans. Her job is pattern recognition across companies — the one thing a per-company tab layout structurally cannot serve.

Weekly bottleneck radar

The sweep cross-references each board plan against raw signals. At Vortex: cert QA queue up three sprints, one engineer sole owner of the launch-blocking bug, a senior QA req open 60 days — none of it in the last board deck, all of it colliding with "cert-ready by October 1."Intervention weeks before the board meeting, not a post-mortem after the slip.

Cross-portfolio playbook

"Who else in the book has fixed unprofitable paid acquisition, and what did it cost them?" One turn over all five decision logs — including the finding that Solstice's wholesale fallback created the ~34% TrailMart concentration in the first place.The question a CRM can't answer, because CRMs shard knowledge by company and she thinks in patterns.

Friday, no kanban

The four production task sweeps ran after every reindex all week; her Friday brief compiles what moved, what's blocked, what's waiting — Solstice's German counter-campaign still waiting on budget sign-off — with approve/dismiss on each nudge.Replaces the entire OperationsBoard. She approves nudges; she doesn't garden a board.

Before 9 a.m.: the radar's overnight verdict (Vortex flagged, four companies clear), one drafted nudge to the Vortex CEO awaiting her approval, prep cards for two portco calls. Meridian's migration clock ticked down but stays inside tolerance — deliberately not in the brief.
Kept out of her view: dealflow and the vault, IC material, LP communications, raw transcripts (extracted commitments only), any per-company tab tree.
MW

Marcus Webb — CEO, Northlane Financial

Runs an invoice-lending fintech, mid covenant breach

His week: credit committee, collections, a board that wants answers, a lender that will want a letter. He did not install a reporting tool — he installed LiveCEO as his company brain; the fund's visibility is a governed by-product. The same holds for his peers: Vortex racing a launch, Meridian on a compliance clock, Portside watching NRR slide, Solstice with CAC underwater.

Onboarding, one afternoon

A conversation, not a settings tree: Drive, Gmail, Slack, Calendar via OAuth; the notetaker joins meetings from his calendar; and the loan-management system — the source that matters — is connected by the conversational connector agent. Delinquency becomes a governed dataset, not a spreadsheet attachment.Data flows in days. No IT project, no monthly reporting-pack ritual, ever.

His covenant, first

His own reindex computes the 4.2% print and his Jarvis fires first — same analysis both sides will see, plus a drafted board narrative, remediation plan, and covenant-letter language in his approvals.He walks into the board conversation presenting the analysis instead of defending against it.

Fund asks broader access

The system shows him exactly which source selectors the fund's view includes and previews the actual filtered wiki the fund's agent reads — because policy is a materialized filesystem view, not a prompt promising to behave. Approve or decline per selector.Trust is structural: no silent surveillance, auditable both directions.

Before 9 a.m.: the delinquency tile with cohort cut, the collections queue for the Q2-2026 manufacturing cohort, a T−30 prep card for the 9:30 credit committee, the draft covenant letter waiting for his edit.
Kept out of his view: the other four portfolio companies, the fund's dealflow and IC memos, its internal risk ranking of Northlane. The walls are symmetric. His full journey → Section 8.
PersonaRitual surfaceException budgetDeepest rightNever sees by default
Investment PartnerMorning brief + meeting prep cards~2–3/day, covenant-grade onlyAsk anything, portfolio-wideTabs, tables, kanban, alert pages, raw transcripts
AssociateMorning brief + inbound-deck triage~3–5/dayReader panel + SQL trace on every numberOut-of-coverage companies, LP material
Operating PartnerWeekly radar + Friday task pulseSlip/threshold exceptions onlyCross-portfolio decision historyDealflow, IC, LP material, task boards
Portfolio CEOCompany-scoped morning briefOwn-company onlyFull own-company brain + upward-view previewOther portcos, fund internals, LP material

A fifth persona — LP / Investor Relations — is deliberately sketched, not built: LP-facing numbers demand audited-figures discipline and a third trust boundary on top of the two we're building. Ship the inside loop first.

THE CEO EXPERIENCE

Data flows up because the CEO wants the tool.

Every fund-side promise depends on portfolio-company data arriving continuously instead of as a 30–45-day-stale monthly pack. That only happens if the CEO wants to install it — so the design constraint is brutal and clarifying: the product must be worth installing even if the fund did not exist. The pitch leads with what she gets, never with what the fund gets: "Northstar is giving every portfolio company a chief of staff. Yours reports to you."

ONBOARDING — DANA, CEO OF PORTSIDE SOFTWARE, HOUR BY HOUR
T+0
Invite from Northstar. Dana clicks, signs in with Google. Workspace portside is created and linked to the fund org.fund↔portco link: build
T+15 min
Connect the stack. Google Drive (2 min), Calendar, Gmail (flagged private-by-default), Slack, GitHub, Jira — all OAuth. She toggles "Auto-record my meetings"; the notetaker will join her calls from the calendar. First index kicks off; she goes to her 10:00.production
T+45 min
First magic, before the index even finishes. Her 10:00 pipeline call was auto-recorded; by 11:10 the transcript is in and the T+10 extraction has drafted two follow-up tasks into her Proposal Inbox.production
T+4 h
Index complete. First cited answers; the knowledge graph renders her company — products, accounts, people, decisions. Same afternoon, with her ops lead: HubSpot, QuickBooks, Stripe via the conversational connector agent (~30–45 min per system) — P&L lines, MRR, pipeline stages land as governed datasets.HubSpot ingester: build · connector agent: exists
Next 7:30
The aha. Her first morning brief: "Atlas Freight ($820K, Committed) is 45 days past expected close. Your champion's last reply was July 10 (thread cited). The account page notes a leadership change at the prospect. Draft a re-engagement email?" She half-knew all three facts. She had never seen them joined. That join — CRM stage × email silence × account intel — is the product.brief rails: exist · PE recipe: new
Day 2
Share-schedule bootstrap. The system finds her June board pack in Drive and proposes: "These 12 metrics are what you already report to Northstar. Approve to publish them as live datasets — here is exactly what each looks like on their side." One approval replaces the monthly email ritual forever.new sweep recipe
Day 7
The fund view is live. Northstar's analyst stops emailing the template. Dana's weekly digest shows the audit line: "Northstar's workspace read 4 shared pages and ran 2 dataset queries this week."cross-org publication: build

Total CEO-attended time: about one hour, split across a day. First value: T+45 minutes. Full aha: inside 24 hours.

What flows up

  • Tier 1 — the schedule, continuously. The agreed KPI series as governed datasets: revenue/ARR, NRR, cash, EBITDA, covenant-relevant metrics (for Northlane: 60+ day delinquency), plan-vs-actual, milestone states. Defined once at onboarding, amended only by mutual edit. The CEO cannot silently switch a scheduled metric off — and can see every send.
  • Tier 2 — curated, CEO-approved. Summaries of fund-attended meetings, flagged risks with the CEO's narrative attached, documents she explicitly shares, generated board packs. Every item is a propose-only cited diff in her inbox: approve, edit, or dismiss.

What stays. Period.

  • Gmail and private Slack — restricted by default even inside LiveCEO's own access layer.
  • Raw Drive documents and full transcripts — the fund gets summaries of shared meetings, never the recording room.
  • HR, personnel, her private notes and chats with her own assistant.
  • The mechanism is enforcement, not promise: the portco materializes a filtered "fund view" of its wiki; the fund's agent mounts it read-only. The agent physically cannot read outside its filesystem root.
THE VALUE EXCHANGE — PRINTED ON THE INVITE SCREEN "You get the assistant. Northstar gets a live feed of the metrics you already owe them every month — and stops emailing you for them. Nothing else leaves your workspace. You can see exactly what they see, at any time, on one screen."

Three terms that turn a suspicious CEO into a yes: symmetric visibility (the "Shared with Northstar" mirror renders byte-for-byte what the fund's agent reads, plus an audit feed of every fund-side access), the fund pays (a portfolio service, like the legal panel), and she keeps the brain at exit (policy revoked, workspace hers — the fund is a temporary subscriber to her system).

STRESS TEST — THE BAD-NEWS CASE

Northlane's covenant, replayed through the boundary

The delinquency series is Tier 1: covenant-relevant, on the schedule, already in every monthly pack. It flows — no CEO action can stop it, and Marcus knew that on day one, which is why it doesn't feel like betrayal when it happens. The evening the refresh carries 4.2%, his Jarvis fires first: "This flags on Northstar's side at tomorrow's brief. Attach context?" He attaches the cohort analysis and the remediation plan his credit committee already drafted. At 7:30, Maya's brief leads with the crossing — with his narrative attached. The first conversation starts at "here's the plan," not "why are we hearing this from a spreadsheet." The system will never let him hide the number — and will never let him be ambushed by it.

THE FUND-SIDE PAYOFF (ESTIMATES TO VALIDATE IN THE PILOT)
MetricMonthly-pack status quoWith upstream flow
Reporting latency30–45 days stale on arrival< 24h (daily reindex, incremental cursors)
Covenant-breach detectionNext reporting cycle — up to 6 weeks, nakedNext sync + morning brief, with CEO narrative attached
Analyst normalization effortest. 10–20 h/month across 5 portcos~0 — datasets land queryable
Board-call commitments trackedPartner's handwritten notesEvery recorded fund-attended meeting, cited, joined to plan
CEO board-pack effortest. 8–12 h/quarter~1 h review — generated from the same datasets the fund reads

The flywheel, stated once: every portco install makes the fund's Today cards sharper; every sharp fund-side moment ("how did you know to ask about Atlas?") makes the next CEO's install conversation shorter. The CEO side is not an add-on — it is the fund product's data layer, wearing a chief-of-staff suit.

BUILT FROM EXISTING BLOCKS

Almost everything already runs in production.

This experience is not a new platform. It is new sweep recipes, one new render tool, and a re-skinned shell over LiveCEO's shipped rails. The honest ledger:

Experience elementLiveCEO building blockStatus
Today's card triggers (the heartbeat)Post-reindex hook chain (postRefresh.ts) + every-minute scheduled-job clock (cron.ts) + NL alerts (alertEval.ts) — each card is a headless agent turn on a tickexists new PE recipes
Cited, propose-only actionsProposal Inbox with evidence capture (taskProposalApply.ts, taskEvidence.ts); managed actions for interactive sends (managedActionCatalog.ts)exists
Answers with citationsAgent engine (agentCore.ts): Claude Agent SDK, Read/Grep/Glob over the curated wiki — no RAG; wiki pills + reader panel (Markdown.tsx, ReaderPanel.tsx)exists
Numbers that can't be inventedDatasets lane: SELECT-only AST-validated SQL over org-scoped Postgres (datasetQuery.ts) + post-turn numeric-claims verifierexists
Composition schema + block rendererNew render_composition write tool (same event-intercept pattern as alertTool.ts) + ~18-block deterministic renderer reusing v1's Recharts kit, MetricCards, graph snippetbuild
Meeting prep & commitmentsT−30 brief (meetingBrief.ts) + T+10 extraction (meetingExtract.ts) + Recall.ai notetaker + calendar datasetexists
Voice in, headline outProduction WebRTC Realtime stack (voiceClient.ts) with pinned tool ask_company_brain; dictation lane as fallbackexists ask_portfolio_brain
CEO-side connectorsComposio OAuth ingesters (Drive, Gmail, Calendar, Slack, Jira, GitHub…) + conversational connector-setup agent → Manifest v2 for ERPs/finance stacksexists HubSpot ingester
Pinned live surfacesLive-dashboard semantics (liveDashboards.ts): stored question, regenerated after every reindex, staleness surfacedadapt
The trust boundaryAccess-management layer: per-policy materialized wiki views (wikiMaterialize.ts), scoped agent filesystem roots — extended to cross-org fund-view mounting + shared-dataset replicationexists cross-org: build
"Shared with Northstar" mirror + audit feedChangelog machinery with withheld-count honesty (knowledgeUpdates.ts) as the doctrine; the mirror screen itself is newbuild
Push channels + the dialSlack bot, Telegram bot, durable email lane — all shipped; the three-position dial is a thin policy over themexists dial
Generated documents (decks, memos)Artifact pipeline (artifactGen.ts) — demoted to documents only, rendered inside a doc-artifact block; never numeric surfacesadapt

Largest genuinely new engineering item: cross-org linking + fund-view materialization + shared-dataset replication — the seam between company brains and the fund brain. It is an extension of shipped access-management machinery, not a new idea.

WHAT WE KEEP FROM V1

The shell dies. The substance survives.

Four v1 assets carry forward directly: the canonical data layer (five internally consistent companies — every generated surface in v2 binds to it), the killer-scene content (the eight sourced answers are precisely what a proactive assistant should surface unprompted), the renderers (charts, metric cards, graph — reframed as blocks in a summonable vocabulary), and the citation contract — made real and clickable. The rule: nothing survives as a place you go. Everything survives as a surface that comes to you.

Vortex Games 9-day buffer Portside Software NRR 118→109 Solstice Outdoor TrailMart 34% Northlane Financial 4.2% vs 3.5% Meridian Clinical Labs CLIA clock

The cast stays. Five companies, five kinds of PE anxiety, one set of canonical numbers that never contradict themselves. Part 1 scripted nine killer scenes; v1 shipped eight of them as canned, cited answers. Four of the nine, replayed as v2 moments:

Scene 1 — "Why did delinquency spike?"

v1 · You navigatedThe associate opens the Credit & Loan Book dashboard; the 60+ delinquency tile is red. Then he asks the sidebar.
v2 · It found youThe card was at the top of Today at 6:58 — pushed, ranked, evidence attached."Why did it spike?" amends the composition: cohort cut, memo excerpt, disclosure clock. The analysis was waiting before the question existed.

Scene 2 — "Which company is most exposed?"

v1 · You navigatedNo view ranks exposure. The navigational answer is five company pages and a mental join — 5+ clicks across 35 tabs.
v2 · One question, mid-call"Where is our concentration risk?"A ranked comparison materializes in one agent turn: Solstice ~34% in TrailMart, Portside healthiest at 6%, citations into both wikis, and the first question for Solstice management. Cross-cutting questions need no navigational home — they never had one.

Scene 7 — "What's new since Friday?"

v1 · A widget among ten"Since Friday, updated 8:02 AM" competes with an opex chart for the same glance; "Open full briefing" is a dead button.
v2 · The brief is the home"What's new since Friday?" — spoken, at 7:55.Voice: "Three things. Northlane's covenant letter draft is ready. Portside's stalled $820K deal has a meeting Thursday. A Solstice competitor launched 20%-off in Germany — the counter-move is waiting on budget sign-off." Each line cited on glass.

Scene 8 — "What aren't they telling us?"

v1 · Tab four of sevenThe Alignment tab's best-in-app content — "what management isn't flagging" — buried where only the trained associate looks.
v2 · Trigger class 3 firesThe card comes to you before the board call."Vortex board committed 'cert-ready by Oct 1' — QA queue math now contradicts it." Plan page, Jira dump, transcript line: every claim cited. Delivered T−30, when the question is still askable.
DECIDE TOGETHER

Fourteen open questions.

Same contract as Part 1's sixteen: each question ships with our lean, and the lean is an invitation to disagree. Chips mark the option space; green is where we currently stand.

1

Generative depth: how do screens actually get made?

A — pre-generated surfaces onlyB — fully generative UIA content in C's skeleton (demo) → C live (product)

Our leanBuild the composition schema and block renderer now; ship the demo on hand-authored compositions. Every hand-authored composition becomes a golden-set eval when the live model takes over. Model B is disqualified for finance — one broken layout in front of an LP-grade audience discredits the data itself.

2

Today + Canvas: one screen with two states, or two tabs?

One screen — Today is the Canvas at restTwo tabsSeparate routes

Our leanOne screen. Tabs are the first CRM cell division — the moment there are two destinations there will be nine (v1's own history proves it). Intent folds the stack into a ribbon; Esc unfolds it. The demo becomes one continuous camera move with zero navigation cuts.

3

Voice: how hard do we commit for the v2 demo?

Wire the production Realtime stackLabeled concept momentCut voice from v2

Our leanWire it — voiceClient.ts is lift-ready and the commute-brief beat is a headline moment. Hard rule either way: no simulated listening. v1's 1.7-second fake mic is exactly the affordance that collapses under one audience question. Voice is input plus headlines; it never reads tables and never creates an answer that isn't on glass.

4

Proactivity aggressiveness: what may interrupt, and when?

Quiet — Tier 0 onlyStandard — Tiers 0–1, ≤3 pushes/dayVigilant — Tiers 0–2, ≤5/dayPage immediately on any covenant event

Our leanStandard as the default; immediate paging only for contractually defined hard triggers. The 3–5/day ceiling is researched, not aesthetic — the over-notifying agent gets muted, then uninstalled. Everything else queues for the morning brief.

5

CEO app packaging: same product scoped down, or a companion app?

Same two surfaces, company-scopedSeparate companion productPortal inside the fund app

Our leanSame product. Marcus gets Today + Canvas scoped to Northlane, plus one extra summonable surface: the "Shared with Northstar" mirror. A separate portal would recreate the reporting-tool framing the whole adoption story exists to avoid.

6

Does anything keep a permanent screen?

Nothing — composer + ribbon are the only chromePinned compositions get a galleryThe CEO mirror stays one tap away

Our leanNothing. Pins are summonable via ⌘K or by asking, never a gallery-as-home. Possible exception worth debating: the CEO's mirror, which carries trust weight and may deserve a permanently visible entry point on the CEO seat.

Decided · 2026-08-25v1 and v2 ship together as one product. The workspace keeps its screens — Portfolio overview, Dealflow, Watchtower, Tasks, company pages — and the v2 experience becomes the Personal cabinet: one tab, the landing tab. Inside the cabinet, the two-surface model stands unchanged (Today ⇄ Canvas, composer, propose-only writes). The dashboards remain destinations for those who want them; the cabinet is where the day starts.

7

Notification channels: where do pushes land?

Slack DM for fund seatsTelegramEmail digestIn-app only

Our leanSlack DM for partners and associates (it's where they live), email + in-app for CEO seats, Telegram where a principal asks for it. All three lanes are shipped production channels; the dial is per-person policy on top.

8

Demo scope for v2: how much do we actually build?

Thin: the Monday 7:42 choreography end-to-endFull block library + live modelSlides/video only

Our leanThin and real: the Today surface with 7 seeded cards over v1's data model, six hand-authored compositions (covenant, exposure, prep, vault, bottleneck, portfolio), the reader panel with working citations, and voice for the brief. One continuous scene beats forty views.

9

Ranking transparency: is "why is this first?" a first-class question?

Yes — deterministic tiers, scores logged, askableRanking is opaque, keep it simple

Our leanYes. The ranking is the product's most consequential opinion; it must be explainable on demand. Deterministic tier-first logic, magnitude then recency within tiers, logged per card.

10

Bad-news sequencing: who learns about a covenant crossing first?

CEO evening, fund at next morning briefSimultaneousFund first

Our leanCEO first — evening, with "attach context?" — fund at the 7:30 brief with the narrative attached. The gap is ritual cadence, not a policy delay: data lands on both sides at the same sync, the fund is never held back, the CEO is never ambushed. Tier 0 hard triggers may page earlier — that is why Maya’s phone buzzed at 6:58 while the narrative still arrived with the 7:30 brief. This is the single sharpest trust decision on the page.

11

History: is the past retrievable only by asking?

Yes — no archive pages, ask for Friday's viewA browsable brief archive

Our leanOnly by asking ("show me Friday's Northlane view", "what fired this month?"). An archive page is a destination, destinations breed badges, and badges breed the CRM. The thread rail covers within-session recall.

12

Dealflow in v2: one scene, or the whole vault?

One scene — "have we seen this pitch before?"Full vault compositionsDefer dealflow entirely

Our leanOne scene. Scene 9 is the fund's institutional-memory showstopper and needs zero vault UI — a question and a materialized comparison. The full deal-card vocabulary waits for the product phase.

13

Home at rest: ranked brief, or near-blank canvas?

Brief-first — Today’s ranked cards are the homeBlank-first — an empty stage until you askAdaptive — blank until the first Tier 0–1 card lands

Our leanBrief-first. A truly blank home is the purest anti-CRM statement — but it makes the proactivity invisible and hands the first move back to the user. The ranked stack is the assistant’s opening sentence; blank-first turns Jarvis back into a search box. This is the page’s strongest implicit opinion — contest it here.

14

The phone: what does a push open into?

Deep-link into responsive Today (mobile web)Channel-native — the Slack/Telegram message is the whole experienceNative app

Our leanA push is a Slack/Telegram/email message whose link opens the responsive Today surface — the 6:58 covenant beat is push → phone → Today, no app install. The Thursday commute readout is a scheduled voice readout over the same lanes (Telegram voice note first; the Realtime voice session once M3 lands). A native app is not a v2 question.