The Deal Calculator in Winston: How-To for Reps

Draft, 20 Oct 2026. The Deal Calculator is being rolled out in stages. If you see “coming soon” on your Home page, it is not switched on for your team yet. Everything below applies once Deal Calc goes live for your team.

What it’s for

The Deal Calculator is where you price a deal and send it to Deal Desk for approval. It replaces the deal-structure spreadsheet. Once the deal is approved, that version stays in Winston as the approved record. A calculator is required when Year 1 ACV is over $500K and optional at or below that. The summary strip shows this as Calculator Required?.

Before you start

Have these ready:

• The opportunity. It must be open. Your own deals list it in Winston, and you can pull any open opp in from Salesforce.
• The Salesforce quote. If the opp has more than one CPQ quote, know which one you’re pricing.
• Deal terms: contract length (1–5 years), subscription start and end dates, the date you expect the order to be signed, payment terms, billing frequency and currency.
• Products and services with quantities and prices (or discounts).
• A short deal rationale: history with the customer, the deal structure, and anything unusual.
• For a cancel/rewrite: the earlier opportunity whose order form is being replaced, plus a PDF of that order form.
• For a renewal or expansion: the current order’s lines. On production deals you add these by hand for now.

Step by step

1. Open the calculator. Choose one of these:
   • In My Deals, open the deal and go to the Calc tab, then click Start calc for this deal.
   • Go to Deal Calculator, click New calculator and search by account name. If the opp isn’t listed, click Search Salesforce for “…” to bring it in.
   • If the deal already has a calculator in progress, you’ll see Continue v… instead. Winston opens the existing calculator rather than making a duplicate.
2. Check the Salesforce fields. Customer, AE, opportunity and close date come from Salesforce and are read-only. If one is wrong, fix it in Salesforce and click Refresh from Salesforce. Read anything listed under Filled from Salesforce — please check.
3. Pick the quote from the Quote drop-down. It defaults to the opp’s primary quote. On production deals, picking a quote records it but doesn’t copy the quote lines in, so make sure your product lines match the quote.
4. Fill in Deal Details. This includes RVP, buyer name and title, Type, Order Effective Date (signed), Cancel / Rewrite, Early Renewal, Contract Length, Same Quantities & Prices Each Year, Local Currency, SVP/C-Suite coaching, Workday Co-Sell, Services Included?, Payment Terms, Billing Frequency and Drawdown Deal. Every question must be answered before you can submit.
5. Add products. Click Add product, then enter Sub Start, Sub End, Qty and either a Price / License or a Disc % (the price fills itself in). The arrow next to a line’s dates copies them down to every line below it. If quantities or prices change by year, set Same Quantities & Prices Each Year to No and use Add year to get one table per year.
6. Add services (if any) under Services on Deal Being Proposed, and a One-Time Discount if needed. The one-time discount applies to Year 1 only, to either Product or Services.
7. Write the Deal Rationale. You can also add Custom Terms Requested if there are any.
8. Check the numbers. The summary strip shows Product, Services and Total TCV (each with ACV) and the Blended Discount. If the opp’s own Year 1 ACV differs a lot from yours, its figure turns orange.
9. Click Save draft as you go. When Before you can submit shows nothing left to fix, click Submit for approval. Just above the version history, the line On submit this goes to: tells you who will review it.
10. Watch for the confirmation. Winston runs its checks and routes the calculator. Slack DMs you a receipt naming the approver(s). If anything fails, the calculator comes back as a draft with a Sent back to draft — fix these and submit again list, and you get a Slack DM listing the same items.

Statuses you’ll see: Draft → Awaiting approval → Approved, Changes requested or Rejected. Each time you rework a calculator, a new version is created (v2, v3…). Older versions remain in the version history.

Who approves, and how long it takes

The routing table below applies once Deal Calc goes live for your team. During the pilot, a small Deal Desk group stands in for these approvers. Either way, the On submit this goes to: line shows the real answer for your deal.

You never approve your own calculator. Approvers get a Slack card and can approve simpler deals straight from Slack. Committee deals are decided in Winston.

Turnaround: [Deal Desk to confirm the target response time.]

If you’re asked for changes

• Slack DMs you the approver’s note. You’ll also see it at the top of the calculator, under Changes requested.
• Click Revise (v…). This opens a new draft with your numbers already filled in. Make the changes and submit again. To abandon the revision, click Discard; the previous version comes back.
• Rejected: the note explains why. Talk it through with the approver, and use Revise if the deal changes.
• Approved with edits: an approver may adjust your numbers and approve in one step. Slack DMs you a list of every change. If their edits push the deal into a higher approval tier, it goes to that tier instead, and you’re told.
• To change an approved deal, use Revise. The new version needs its own approval.

Scenarios (comparing options)

To compare structures, such as 2-year vs 3-year or different discounts:

• Click + on the scenario tab bar. It makes a draft copy of the current numbers, and the original stays as it was. Tabs are labelled Scenario 1, Scenario 2, and so on.
• Edit each tab separately. You can delete a never-submitted scenario with the × on its tab.
• Click Submit N scenarios for approval to send them together. All of them go in at once, so every scenario must pass its checks first. The set is routed at the highest tier among the scenarios.
• The approver decides each scenario individually (usually approving one).

Comments and @mentions

Use the comments panel to talk to Deal Desk about a calculator. Type @** to mention someone on the deal, and they get a Slack DM. Everyone else on the calculator is notified of new comments. Comments are also posted to the opportunity’s Chatter in Salesforce, and the opp’s own Chatter shows up in the thread. Comments don’t change the calculator’s status. Approvers use Request changes** to send it back to you.

Common warnings and what they mean

Warnings (orange) won’t stop you submitting. Winston repeats them in a Before you submit box, and you can click Submit anyway.

• “Subscription dates span X but Contract Length is Y”: your dates and the term don’t match. If the dates run longer, TCV only counts the contract length.
• “Line … runs X but the contract is Y”: one product’s dates don’t cover the full term. This is fine for a deliberately short product.
• “Subscription start is less than a month after the order effective date”: subscriptions usually start at least a month after signing.
• “SF reports $X Y1 ACV” in orange: the opp’s ACV differs by more than 5% from yours. Check which one is right.

Blockers must be fixed before you can submit:

• Missing answers. Any blank Deal Details question, the rationale, the RVP, or a product line without a quantity or price.
• Drawdown minimums. A drawdown needs a term of at least 2 years and a drawdown TCV of at least $1M, or $500K for Emerge opps. One-time discounts don’t apply to drawdowns, so that block is greyed out.
• Cancel / Rewrite = Yes. You need to pick the prior opportunity, upload its order form(s), tick the existing lines being cancelled, and explain why.
• Currency. Non-USD deals use Salesforce’s quarterly corporate FX rates. All routing and approval figures are in USD. If the rate is marked PROVISIONAL or has changed, click Reload rates. A calculator priced at last quarter’s rates is sent back with “Re-quote: exchange rates changed”.
• Year tables vs. Contract Length. The number of year tables must match the contract length.

Getting help

• Deal Desk / Jeremy Anderson: pricing policy, discounts, drawdowns, cancel/rewrites.
• [Jeremybot — placeholder, details to come]
• A problem with Winston itself (can’t open, error message, wrong data from Salesforce): [Winston support contact to confirm].