Strategy & Planning

How to run annual planning as Chief of Staff and Founder's Office

Strategy & PlanningFor Chief of Staff and Founder's Office4 apps12 steps~24 min to set up

Annual planning as a chief of staff means you're the one assembling the full picture while every functional leader is living inside their own silo. You're pulling Q4 actuals out of QuickBooks, chasing the VP of Sales for a HubSpot pipeline snapshot, reading six different versions of a Google Doc OKR template, and trying to reconcile headcount plans that live in a spreadsheet nobody has updated since September. The board wants a three-year model. The CEO wants scenario comparisons by Friday. You have none of these numbers in one place, and you are manually stitching them together across five tabs, two Notion pages, and a chain of Slack threads.

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Strategy & PlanningFor Chief of Staff and Founder's Office4 apps12 steps~24 min to set up

Outcome

What you'll set up

A connected annual planning workspace that pulls live actuals from QuickBooks and Stripe into your budget vs. plan view — so you're not chasing numbers from finance, you're reading them directly

A scenario model with at least three 'what if' cases (double hiring, hold headcount, raise prices) built against your real baseline revenue and burn — ready to share with the CEO and board before the offsite

A board-ready slide deck and written narrative auto-generated from the planning data, so the Sunday-night deck-building sprint becomes a 45-minute review instead

The Starch recipe

Apps, data, and prompts

The combination of Starch apps, the data sources they pull from, and the prompts you use to drive them.

Apps used

Scenario Analysis Budgeting Presentation Agent Knowledge Management

Data sources & config

Starch syncs your QuickBooks data on a schedule (invoices, bills, payments, journal entries, and vendor data) and syncs your Stripe data on a schedule (charges, subscriptions, payouts) — both feed the Budgeting and Scenario Analysis apps with real actuals. Plaid syncs your bank transactions and balances on a schedule to anchor cash position in the runway model. HubSpot is connected from Starch's integration catalog and queried live when the planning workspace needs pipeline and ARR data. Notion is synced on a schedule so the knowledge base pulls in existing OKR docs and planning artifacts. Google Calendar is synced on a schedule to coordinate offsite logistics and planning sprint milestones.

Prompts to copy

Build me a scenario analysis comparing three annual plans: one where we hold headcount flat, one where we add 20 people in H1, and one where we cut burn by 15%. Use our actual Stripe revenue and Plaid cash balance as the baseline. Show runway, burn rate, and break-even date for each scenario.

Set up an annual budget tracker with categories matching our QuickBooks chart of accounts — R&D, G&A, Sales, Marketing, COGS. Pull in actuals from QuickBooks and show me a pace indicator for each category versus the plan we agreed in November.

Build me a 12-slide annual planning board deck. Slide 1: 2025 recap with revenue, burn, and key milestones. Slides 2-4: three-scenario financial outlook with charts. Slide 5: 2026 headcount plan by department. Slides 6-9: OKRs by function with owners. Slide 10: risks and mitigations. Slide 11: asks from the board. Slide 12: appendix with model assumptions.

Create a planning knowledge base that archives this year's OKRs, the board-approved budget, the headcount plan, and the scenario model assumptions — so any exec or new hire can search for the rationale behind any 2026 decision.

Run these in Starch → or paste them into your favorite agent

Walkthrough

Step-by-step

1 Connect QuickBooks, Stripe, and Plaid as scheduled-sync sources. Starch will pull in your full chart of accounts, transaction history, and cash position automatically — this is the baseline every planning number gets anchored to.

2 Open the Budgeting app and tell Starch: 'Set up an annual budget with categories matching our QuickBooks chart of accounts and pull in actuals from the last 12 months.' Starch generates suggested allocations from your historical spending so you're not starting from a blank row.

3 Audit the suggested category allocations with each functional lead. Use the Budgeting app's variance view to show where last year's actuals diverged from plan — this is your first conversation starter with the CFO and department heads.

4 Open the Scenario Analysis app and describe your three planning cases in plain language. Starch builds each model using your live Stripe and Plaid baseline, so the starting numbers aren't hypothetical — they reflect what's actually in your accounts today.

5 Run the scenario comparison and identify which assumptions move the needle most on runway. Share the scenario output with the CEO before the executive offsite so the team is debating real numbers, not last quarter's gut feel.

6 Connect HubSpot from Starch's integration catalog and tell Starch: 'Add a pipeline view to the annual planning workspace showing open deals by stage, expected close date, and weighted ARR.' This keeps the revenue plan honest against what sales is actually seeing in the funnel.

7 Sync Notion so Starch can read your existing OKR docs and department plans. Tell Starch: 'Ingest all Notion pages tagged annual-planning-2026 and build a searchable knowledge base with the full context behind each OKR.' Now there's one place to find the rationale, not six Notion pages.

8 Use the Presentation Agent to generate your board deck. Describe the structure you want, reference the scenario model and budget data you've built, and get a complete draft in minutes rather than building slides from scratch at 11pm.

9 Run a red-team review of the deck against the planning knowledge base. Tell Starch: 'Flag any claim in the board deck that contradicts the assumptions documented in the planning knowledge base.' This catches the inconsistencies that usually surface when a board member reads the appendix.

10 Set up a recurring monthly check-in automation: 'On the first Monday of each month, pull actuals from QuickBooks and Stripe, compare them against the annual budget, and post a variance summary to the #exec-team Slack channel.' This keeps the annual plan a living document, not a binder that gets opened at the next board meeting.

11 After the board approves the plan, archive the final budget, scenario assumptions, headcount plan, and OKRs in the knowledge base with a 'board-approved 2026' tag. When a functional lead asks in August why their headcount allocation is what it is, the answer is searchable.

12 Schedule a quarterly planning refresh on your Google Calendar (synced through Starch) and wire it to the Scenario Analysis app so that every 90 days you're reviewing actuals-vs-plan with live numbers — not a snapshot someone exported three weeks ago.

See this running on Starch

Connect your tools, describe what you want, and the agent builds it. Closed beta is free.

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Worked example

November 2025 Annual Planning Sprint — 150-person B2B SaaS, $18M ARR

Sample numbers from a real run

2025 closing ARR (Stripe actuals)	18,200,000
2025 total opex — actuals (QuickBooks)	14,800,000
Cash on hand (Plaid)	6,400,000
2026 plan — hold headcount scenario: implied runway	22
2026 plan — +20 hires H1 scenario: implied runway (months)	14
2026 plan — burn reduction 15% scenario: implied runway (months)	28

The company closes November with $18.2M in ARR and $6.4M cash. The chief of staff opens the Scenario Analysis app and types: 'Compare three 2026 plans using our Stripe ARR and Plaid cash as the baseline: hold headcount flat at 150, add 20 hires in H1, or reduce total opex by 15% vs 2025 actuals.' Starch pulls the live numbers and builds all three models. The hold-headcount scenario shows 22 months of runway and a path to cash-flow break-even in Q3 2026. The +20 hires scenario compresses runway to 14 months — which means a Series B raise needs to close by Q2 2026 at the latest, a constraint that wasn't obvious until the model made it visible. The burn-reduction scenario extends runway to 28 months but requires cutting the marketing budget by $900K, which the Growth Analyst app shows would reduce top-of-funnel by roughly 35% based on last year's spend-to-pipeline ratio from HubSpot. The chief of staff presents all three to the CEO and CFO on Wednesday. By Thursday, the board deck is drafted using the Presentation Agent — 12 slides built from a two-paragraph description, with the scenario charts imported directly from the model. The Friday board call starts with everyone looking at the same numbers for the first time.

Measurement

How you'll know it's working

Runway in months under each approved scenario — reviewed monthly against actuals

Budget vs. actuals variance by department — flagged when any category exceeds 10% over pace

OKR completion rate by function at each quarterly check-in

Days from fiscal year-end close to board-approved annual plan (target: under 30)

Number of planning assumptions that required revision after Q1 actuals came in

Comparison

What this replaces

The other ways teams handle this today, and how the Starch version compares.

Spreadsheet + Google Slides (manual)

You control every cell, but the numbers are stale the moment you paste them, and you're rebuilding the same deck every quarter from scratch.

Anaplan or Adaptive Insights

Purpose-built enterprise planning tools with deep modeling capabilities, but they require a dedicated FP&A admin to configure and cost multiples of what a 150-person company wants to spend on a planning tool.

Notion + manual data pulls

Notion is excellent for documenting plans and OKRs, but it has no native connection to QuickBooks or Stripe, so the numbers inside it are only as current as the last time someone updated them by hand.

Mosaic or Runway (financial planning SaaS)

Strong financial modeling for operators, but focused on finance — they don't cover OKR tracking, board deck generation, or knowledge management, so the chief of staff still needs to stitch together the full planning picture across separate tools.

On Starch RECOMMENDED

One platform — scenario planning, quarterly budgeting, presentation agent all running on connected data. Setup in plain English; numbers stay current via scheduled syncs and live agent queries.

Try it on Starch →

FAQ

Frequently asked questions

Does Starch actually pull our real QuickBooks numbers, or do we have to export and upload a file?

Starch syncs your QuickBooks data on a schedule — invoices, bills, payments, vendors, and journal entries come in automatically. You don't touch an export. One honest caveat: QuickBooks report views like P&L and Transaction List are temporarily unavailable due to an upstream connector issue; entity-level data (the individual bills, invoices, and journal entries) syncs normally, and those are what the Budgeting app uses to build the actuals view.

Our CFO has the financial model in a Google Sheet with 15 tabs of custom logic. Can Starch replace that?

Probably not entirely, and we won't pretend otherwise. Starch's Scenario Analysis app is built for comparing directional futures fast — hiring scenarios, burn reduction, revenue growth rates — using your live Stripe and Plaid data as the baseline. If your CFO has a model with bespoke amortization schedules, custom waterfall logic, or complex equity modeling, that level of specificity belongs in a spreadsheet. Where Starch helps is keeping the planning workspace connected to live actuals so the spreadsheet model gets fed real numbers, not stale exports.

How does the annual plan stay current after the board approves it in December? Most plans are out of date by February.

You can set up a monthly automation that pulls actuals from QuickBooks and Stripe, compares them against the approved annual budget, and posts a variance summary to Slack. The plan becomes a living check-in rather than a one-time document. When assumptions change — say, a big deal slips or you decide to delay a hire — you update the scenario in Starch and the comparison view updates automatically.

Is Starch SOC 2 certified? We'd be connecting QuickBooks and Stripe, which have real financial data.

Starch is not SOC 2 Type II certified today. That's a real consideration if your security review requires it. We're transparent about it rather than burying it in fine print. If your company's data policy requires SOC 2 Type II before connecting financial systems, that's a blocker you should know about upfront.

We use HubSpot for pipeline. Can the annual plan pull in ARR projections from deals, not just Stripe actuals?

Yes. Connect HubSpot from Starch's integration catalog and the agent queries it live when your planning workspace runs. You can tell Starch: 'Add a revenue projection view that combines Stripe ARR actuals with the weighted value of open HubSpot deals expected to close in H1 2026.' That gives you a blended view of committed and projected revenue in the same planning surface.

The Presentation Agent is listed as 'in development' — what do we do for board deck creation today?

The Presentation Agent is currently in development; you can request beta access to get notified when it launches. In the meantime, you can use Starch to build and export the underlying data — scenario charts, budget variance tables, OKR summaries — and drop those into your existing Google Slides or PowerPoint template. The data assembly is where the time actually goes; the formatting work is faster once you have clean numbers.