Handbook

• •Home — your dashboard: tiles for open deals, deals closing in 30 days, deals out for signature and open requests, then panels for My deals, My deal calcs and My requests.
• •My Deals — every open deal you own, sorted by close date: Account, Opportunity, Stage, 1st Year ACV, Close Date, Quarter and Documents. See My Deals.
• •My Requests — what you’ve asked legal for and where each request stands. See Legal requests.
• •Deal Calculator — build, submit and track deal calcs. See Deal Calculator.
• •Handbook — this page.
• •Feedback (bottom of the sidebar) — report a problem from any page.
• •Your name (bottom left) — Notifications, Account settings and Sign out.

You see your own book: your deals, your calcs and your requests. Approvers and legal see queues across many reps. A few things are only shown to reviewers — for example the Green / Yellow / Red triage colour on a calc.

RVPs see their team’s deals and calcs, plus Deal Desk.

• •Deals, owners, stages, close dates and amounts come from Salesforce opportunities.
• •Legal requests become Salesforce Cases.
• •Approved deal calcs are recorded back on the Salesforce opportunity (see what goes to Salesforce).
• •If something in Winston looks wrong, fix it in Salesforce first — Winston follows Salesforce, not the other way around.

1. 1.Open Deal Calculator in the sidebar and press New calculator. (Or open a deal in My Deals, go to the Calc tab and press Start calc for this deal.)
2. 2.Under Start from a deal, your own open deals are listed first. Type in Search deals by account name… to search all open deals.
3. 3.Not listed? Type at least two letters and press Search Salesforce for “…”. Pick the opportunity; Winston shows Bringing that opportunity into Winston… and starts the calc.
4. 4.If you already have an open calc on that deal, Winston opens it instead of making a duplicate.

Tip · Every calc has to come from an opportunity — there’s no blank calc. That’s what links it to the right deal in Salesforce.

At the top of the calc, From Salesforce shows what Winston read from the opportunity: Customer, Opportunity (a link), AE / AM, RVP, Buyer, Buyer title, Type, Salesforce close date, Salesforce term, SVP / C-suite coaching and Workday co-sell. Only fields Salesforce actually has are shown.

You can’t edit these. To change one, change the opportunity in Salesforce. Then press the round Refresh icon (Refresh from Salesforce). Refresh only touches these fields, and saves straight away. Refresh is there while the calc is a draft.

Estimated Close Date works the same way: when Salesforce has it, it’s read-only with the note “From Salesforce. To move it, change the Close Date on the opportunity, then press Refresh.” If Salesforce has no close date, you can type one.

Heads up · You can’t change the close date in Winston. Change the Close Date on the opportunity in Salesforce, then press Refresh on the calc.

Anything Salesforce didn’t fill in is asked for here. Most are quick Yes / No answers. The ones people miss: RVP, Payment Terms (Net 30 / 45 / 60 / 90 / Other), Billing Frequency (Annual Upfront / Quarterly / Monthly / Other) and Deal Rationale.

• •Cancel / Rewrite = Yes: pick the prior opportunity, upload the order form(s) being cancelled or rewritten, tick the existing lines and explain the cancellation.
• •Drawdown: answer Drawdown Deal and enter Drawdown TCV (Product Only). Drawdowns need at least 2 years and $1M TCV ($500K for Emerge). The product table becomes a Rate Card.
• •One-Time Discount: an amount and whether it’s for Product or Services. It applies to Year 1 only and shows as a negative line (“One-Time Discount - Product/Services”). It can’t be more than the Year 1 net, and it’s not available on a drawdown.

• •Products on Deal Being Proposed has a line per product: Product, Sub Start, Sub End, Duration, Existing, List / Unit, Ext. List, Qty, Price / License, Disc %, Net Ext. (ACV), Uplift and TCV. Typing a Disc % fills in the price for you.
• •Use Add product for more lines and Copy dates to all lines to give every line the same Sub Start and Sub End.
• •Contract length comes from the Sub Start / Sub End dates — there is no separate term box. The maximum is 5 years.
• •If quantities or prices change by year, answer No to Same Quantities & Prices Each Year and use Add year (up to 5) to get a table per year.
• •Services on Deal Being Proposed works the same way. Add a service, or tick “No services” for that year.

Pick the Local Currency: USD, EUR, GBP or CAD. Enter prices in that currency. Winston works out totals, routing and triage in USD, at this quarter’s rate. The strip above the lines shows the rate. Show amounts in: switches the view between the local currency and USD.

When the currency isn’t USD, the one-time discount field becomes Amount (USD) — enter it in dollars. If the rate is provisional or stale you’ll see Reload rates. A new version (Revise) picks up the current quarter’s rate.

Want to show options (say, 2-year vs 3-year)? Use the tab strip above the calc. The + tab adds a scenario — a draft copy of the current numbers, named “Scenario 2”, “Scenario 3” and so on. The original isn’t changed. A never-submitted scenario can be removed with × → Delete scenario.

All draft scenarios are submitted together with Submit N scenarios for approval. They go to one approver, at the highest approval level any of them needs. The approver decides each one separately — approve one, send another back, reject a third — or approves them all at once.

Under the calc, Before you can submit (N to fix) lists everything that blocks submission. Each item says exactly what’s missing, for example:

• •Required answers: customer name, opportunity ID / quote #, AE, RVP, buyer name, deal type, Cancel / rewrite?, Early renewal?, SVP / C-suite coaching?, Workday co-sell?, Drawdown?, Same quantities & prices each year?, payment terms, billing frequency, deal rationale.
• •“Other” payment terms or billing frequency need a description.
• •Every product line needs a product from the price list, a quantity, a price per license, and both Sub Start and Sub End (End after Start).
• •Each year needs a service or a tick for “No services”.
• •Cancel / rewrite and drawdown deals have their own required items (see Deal details above).

Tip · Worth a double-check (won’t block submit) lists warnings — for example a line whose dates don’t match the term, a term that differs from Salesforce, or a start date less than a month after the close date. Read them; you can still submit.

1. 1.Press Save draft.
2. 2.Check On submit this goes to: — it shows who will approve and why.
3. 3.Press Submit for approval (or Submit N scenarios for approval). If there are warnings, Winston shows Before you submit — press Submit anyway to go ahead.
4. 4.You’ll see a confirmation and get a Slack DM (📨 Submitted …). The approver gets a Slack card to review it.
5. 5.Winston re-checks the calc against Salesforce. If something doesn’t match, it comes back to draft with a list of fixes and a Slack DM (⚠️ … wasn’t submitted).

Approvers see a triage colour on each calc; you don’t, but it’s worth knowing what drives it, because it’s the deal policy. Green means no flags. Yellow means something needs a higher sign-off. Red means something is outside policy and needs the deal committee, or isn’t allowed.

What raises a flag, for example: a product discount over 20% (yellow) or over 35% (red). A services discount over 20%. A large one-time discount. Payment terms past the field limit (yellow) or over Net 60 (red). Billing that isn’t Annual Upfront. Drawdowns and cancel / rewrites. Custom terms, SVP coaching or Workday co-sell. MFN, termination-for-convenience or side letters (red).

The deal policy guide is the source of truth. Use Deal policy guide (the slides) or Ask the policy guide (ask a question and get an answer with the slide it comes from) in the Deal Calculator — inside a calc they’re Policy guide and Ask policy.

Winston picks the approver from the calc, in this order:

1. 1.Cancel / rewrite → Jeremy.
2. 2.Drawdown → Jeremy.
3. 3.First-year ACV of $500K or more (in USD) → Jeremy.
4. 4.Everything else → a Deal Desk approver — the opportunity’s Deal Desk Assignee in Salesforce where there is one, otherwise by your manager and region.

• •You can never approve your own calc, and neither can the deal owner. If that leaves nobody, it goes up a level.
• •One approver’s decision settles it.
• •Your RVP is a required field on the calc but isn’t an approver in Winston.
• •Approvers can hand a calc on to another approver; the calc then shows the new approver.

Approvers choose Approve, Request changes (a note is required) or Edit & approve (they adjust and approve in one step — you’ll get an “approved with edits” DM).

• •Draft — yours to edit. Nobody else is notified.
• •Awaiting approval — submitted; with the approver.
• •Changes requested — the approver sent it back with a note. Press Revise to make the changes.
• •Approved — done. Winston records it on the opportunity.
• •Rejected — not approved (scenarios can be rejected one by one). Talk it through with the approver before trying again.
• •Superseded — an older version replaced by a newer one. Kept read-only for the record.
• •Discarded — a revision draft you threw away.

Revise (v2) opens the next version of the calc as a draft with everything copied in. It’s offered on calcs that are awaiting approval, changes requested, approved or rejected.

One open version per deal. A version is “open” while it’s a draft, awaiting approval or changes requested. While one is open, Revise is greyed out with “v2 is already … — finish or discard it first”.

Revising an approved calc? The new version needs its own approval. Revising one that’s awaiting approval? It leaves the approver’s queue. Either way, the old version becomes Superseded and stays readable. Versions shows the history and lets you compare versions.

Heads up · Only one version of a deal can be open at a time. If Revise is greyed out, finish or discard the open version first.

• •A brand-new draft (v1): Delete → Delete this draft calculator? → gone for good.
• •A revision draft (v2+): Discard → Discard this draft (v2)?. It stays in the history as Discarded, and the previous version goes back to the status it had.
• •Only the calc’s author or owner can delete or discard. Submitted calcs can’t be deleted — ask the approver to request changes, then revise.

• •Deal Calculator Details on the opportunity gets an “Approved Deal Calculator” block with a link back to the calc and a summary of the approved terms. Only Winston’s block is replaced; anything else in the field is kept.
• •Chatter: Winston comments, and the decision (✅ Approved / 🔁 Changes requested / ❌ Rejected, with the note), are posted to the opportunity’s Chatter where Chatter sync is on.
• •The approved calc shows a line at the bottom saying whether it was written to Salesforce (Approved record written to Deal Calculator Details on the Salesforce opportunity …) or not, and why.
• •Not changed: your CPQ quote. Calc approval does not approve the quote, change quote lines or post to the quote. The Quote picker on the calc only records which quote the calc is for.

Heads up · Approving the calc does not approve your CPQ quote. The quote still needs its own approval in Salesforce.

• •Open the calc. Comments is the panel on the right (or below the calc on a narrow screen).
• •Visible to: you (the rep), the calc’s approver(s), your RVP, executives and the Winston team. Nobody else.
• •Comments belong to a version. The v2 chip means “comments stay on version 2”; a link like 3 earlier on v1 → takes you to the earlier conversation.
• •Decisions show in the thread too: “Approved by …”, “Changes requested by …” with the approver’s note.
• •Comments are permanent — they can’t be edited or deleted. Up to 4,000 characters each.

1. 1.Click Write a comment… @ to mention.
2. 2.Type. Use Shift+Enter for a new line.
3. 3.Type @ and a name to mention someone; pick them from the list (Enter or Tab picks the top match, Esc closes the list). The line below shows “Mentioning …”.
4. 4.Press Enter (or the send button) to post.

Heads up · Enter sends straight away, and comments can’t be edited or deleted. Use Shift+Enter for a new line.

• •Every new comment sends a Slack DM to everyone else on the calc: “💬 … commented on *calc* (v2):” with the comment quoted.
• •If you were @mentioned, the DM says “💬 … mentioned you in a comment on …”.
• •The DM has an Open in Winston button and says “Reply in Winston — replies here don’t reach the comment thread.”
• •Replies typed in Slack do not sync back. Always reply in Winston.

Heads up · Don’t reply to the Slack DM — your reply stays in Slack and the approver never sees it in Winston. Press Open in Winston and reply there.

• •Winston → Chatter: when Chatter sync is on, the line under the comment box says so. Each comment is posted to the opportunity’s Chatter as “Name (via Winston, Deal Calc v2): …”. People on the calc become real Chatter @mentions, so their Salesforce bell rings. Decisions are posted too: ✅ Approved, 🔁 Changes requested or ❌ Rejected, with the note.
• •Chatter → Winston (reading): the thread shows the opportunity’s Chatter, and the selected quote’s Chatter (read-only), tagged Salesforce or Salesforce · Quote ….
• •Chatter → Winston (replies): when switched on, a reply to a Winston-posted Chatter message (within 30 days) comes back as a comment, and people on the calc get “💬 … replied in Salesforce Chatter on …”. New top-level Chatter posts are not brought in.
• •Winston never posts to the CPQ quote’s Chatter.
• •If a comment couldn’t be copied to Chatter, it’s still saved in Winston and marked as not posted.

• •Winston calc comment → stays in Winston, DMs everyone on the calc in Slack, and is copied to opportunity Chatter (when sync is on).
• •Slack DM reply → stays in Slack only.
• •Reply to Winston’s post in opportunity Chatter → shown in the thread; comes back as a Winston comment when Chatter replies are on.
• •New post in opportunity Chatter → shown in the thread as Salesforce Chatter; not a Winston comment.
• •Approver’s decision → in the thread, in your Slack DMs, and posted to Chatter (when sync is on).

Tip · When in doubt: write it in the calc’s Comments box. That’s the one place everyone on the calc is guaranteed to see.

1. 1.In Slack, open your DM with the Winston app. You’ll see Customer requests, Legal questions and My requests. (If you just type, Winston asks whether to Open the form or treat it as a question.)
2. 2.Choose Customer requests. In New legal request, pick the Request type and Whose paper? (Our template / Counterparty’s paper / N/A — not a contract), then Next.
3. 3.Fill in the second page: the account or opportunity, Subject, Details, and anything the type needs (signer details for NDAs and ESAs, the quote for Order Forms and Quote Assistance, amendment details).
4. 4.Attach documents (up to 3 files, 10MB each). If it’s the customer’s paper, attaching it is required.
5. 5.Press Submit. Winston replies ✅ Filed as Case … and starts a thread: “This thread is home for this request — updates, and anything legal needs from you, land here.”

• •Contracts: Beta Terms, DPA, ESA/MSA, NDA, Order Form.
• •Amendments: Amendment.
• •Questionnaires: AI Questionnaire, InfoSec Questionnaire, Privacy Questionnaire.
• •Other: AI Addendum, Outcome Study Legal Review, Quote Assistance, Services SOW, Other.

• •Your request becomes a Salesforce Case and lands in legal’s triage queue.
• •Legal assigns an owner (some request types are assigned automatically). You get “👋 Your request is with … from legal — they’ll reply right here in this thread.”
• •Status moves from waiting for legal → assigned → in progress → closed. My Requests shows the Salesforce Case status when there is one.
• •When it’s done you’ll hear it was resolved and closed. If it’s reopened, you’ll get a note in the thread.

• •Your side is the Slack thread under ✅ Filed as Case …. Reply there — Winston relays your message to the owner.
• •Legal’s side: the owner replies from their own Slack thread or from Winston, and it arrives in your thread.
• •Files you drop in the thread are saved to the Case.
• •You don’t need to reply on the Salesforce Case or in Winston — the thread is the conversation.

My Requests in the sidebar lists everything you’ve asked legal for, with Open, Closed and All filters. Columns: Request (subject and type), Account (and opportunity), Status, With (the owner, “Not yet assigned”, or “Self-serve”), Filed, and Case (a link to the Salesforce Case).

It’s read-only — replies from legal arrive in the Slack thread you asked in. Your open requests also appear on Home.

• •In-app notifications — show notifications in the bell.
• •Slack DMs — Slack DMs when you’re mentioned or someone comments.
• •Email notifications — email to your BetterUp address, only for the moments you tick.
• •Email moments for calcs: a calc you approve is submitted. A calc is handed or assigned to you. Someone comments on a calc you’re on. Your calc is approved, sent back or rejected. Also: someone @mentions you or replies to your comment, and updates on legal requests you filed.
• •Not emailed (Slack only): your own submit confirmation, calcs sent back to draft on submit, discards and new versions.

Your open deals from Salesforce, sorted by close date, with first-year ACV totals at the top. The Documents column shows where each deal document stands.

Click a deal to open its drawer: Overview, Updates & Notes (status notes, Chatter and Slack), Activity (including deal comments — these have Reply, Edit, Delete, reactions and attachments) and Calc (your calcs for the deal and Start calc for this deal).

Accounts lets the legal team search a customer and see its opportunities, legal requests and calcs together. It isn’t in the AE sidebar; your own view of the same things is My Deals, My Requests and Deal Calculator.

• •Deal not in the calc picker → it’s probably at Pipeline. Use Search Salesforce. See Start a calc.
• •Close date or another field won’t edit → it comes from Salesforce. Change it there, then Refresh.
• •Sent back to draft right after submitting → read the banner; usually Refresh from Salesforce and submit again.
• •Approver replied in Slack but nothing in the thread → Slack replies don’t sync. Ask them to reply in Winston. See Comments.
• •`No … exchange rate` on a non-USD calc → press Reload rates; if it persists, send Feedback.
• •Legal request stuck → Nudge from My requests in the Winston Slack DM (once per 24 hours).
• •A page shows nothing or an error → reload the page. If it keeps happening, send Feedback.

• •Deal terms, discounts, approval decisions → your calc’s approver (Deal Desk, or Jeremy for committee-level deals), through the calc’s Comments.
• •Deal policy → Deal policy guide / Ask the policy guide first, then Deal Desk.
• •Contracts and legal questions → Legal, through your request’s Slack thread.
• •Salesforce data (owner, stage, close date, amounts) → fix it in Salesforce, or ask your sales ops contact.
• •Winston itself (access, bugs, ideas, this handbook) → Feedback, or Nick Raffey, who owns Winston.