Brennan WardDeal Desk

Demos

See the assistant work

Two full recorded walkthroughs with shorter clips cut from each, and a static version of the daily deal brief. One shows how I work a complex renewal pricing request. The other shows the Deal Strategy Assistant, which runs on a demo Salesforce org and Slack workspace. All data is fictional.

Complex pricing: working a renewal request

The full recording shows how I think through a pricing request out loud. The scenario is a fictional customer, Harborline Logistics, renewing a subscription with seats and committed credits. The AE sends eleven asks, and I work from the existing contract to a first-round counter. The Salesforce org, the order form, and every number are illustrative. Each clip below is tied to the interview questions it helps answer.

Full walkthrough · 52:56

Working a complex renewal request, start to finish

The complete recording of how I work a Deal Desk pricing request: the account executive's work item in Salesforce, the existing contract and order form, and my read on each of the customer's eleven renewal asks. The customer, the order form, and the Salesforce org are fictional.

The order form on screen in this recording is my first draft, and it labels $318.75 as a per-year price. That was wrong. $318.75 is a monthly price per seat, so the $189,656.25 on that form is monthly revenue, and the real annual figure is $2,275,875. I catch it myself at 40:36 (Clip 14). The Salesforce order form is corrected.

Helps answer:Complex enterprise dealPrice analysisGive/getSaying no to SalesLegal, Finance, and Product

Clip 1 of 18 · 2:22

Read the request first, then decide on a call

The AE opens the request as a work item. I read it for what is reasonable and what is a throw-at-the-wall ask, check the dates (renewal ends Dec 6, customer wants to sign by Nov 6), and work through it asynchronously before booking time with the AE.

Helps answer:Saying no to SalesDeal flow efficiency

Clip 2 of 18 · 1:29

Ramp or discount option? Don't bank on an acquisition

The customer wants seats that ramp from about 220 as an acquisition closes. The trigger is out of anyone's control, so I lean toward a discount option agreement that spells out the volume discounts instead of a locked ramp.

Helps answer:Give/get

Clip 3 of 18 · 3:53

Ask what an ask means before you price it

Rollover credits, overages, a "true-down", support at 5%, quarterly billing at net 60, and a renewal cap. Where the wording is jargon and I'm guessing at the meaning, I ask the AE to clarify instead of building an offer on a guess.

Helps answer:Complex enterprise dealSaying no to Sales

Clip 4 of 18 · 2:41

Where I draw a hard no, once

Termination for convenience after month 12 with a refund turns a three-year price into a one-year deal with the first year refunded. I say no to the whole request up front, so no follow-up version of it comes back. I also ask what "MFN pricing" means in plain terms.

Helps answer:Saying no to Sales

Clip 5 of 18 · 2:29

Ask Sales for the customer's top three

I ask why the customer wants to sign by Nov 6 when the renewal runs to Dec 6. With eleven asks on the table, I also ask the AE which three the customer cares about most, so the offer is built around them. A deal that works for both sides moves faster than a line in the sand.

Helps answer:Give/getSaying no to Sales

Clip 6 of 18 · 3:11

Pull the current contract before anything else

Renewals start from the baseline. I open the executed order form from the closed-won opportunity and note the MSA that governs it, the 24-month term, and the billing terms today (annual upfront, net 30). That makes a move to quarterly net 60 a large change.

The order form on screen here is my first draft, and it labels $318.75 as a yearly price. It is a monthly price per seat. I catch this in Clip 14.

Helps answer:Complex enterprise dealPrice analysisLegal, Finance, and Product

Clip 7 of 18 · 4:21

Spot the re-rate: fewer units at a lower price

The customer asks to buy fewer seats and credits, and for a lower unit price on each. Each ask is fine alone. Together they re-rate products they already own. I line up what they would pay under the ask against what they pay today.

The $189K I call the annual spend here is actually the monthly number. The real annual spend is about $2.28M. I catch it in Clip 14.

Helps answer:Complex enterprise dealPrice analysis

Clip 8 of 18 · 4:57

Use the contract's own language

The order form already says unused credits expire, overages bill at $1.10, and seat price can rise at most 7% at renewal. I use that wording to push back on rollover, and to turn the 7% cap into the opening counter: a firm price for fewer seats with volume discounts as they grow.

This opening counter was built before I priced the real size of the deal. I walk it back in Clip 17.

Helps answer:Complex enterprise dealPrice analysisGive/get

Clip 9 of 18 · 1:36

Who else needs to weigh in

I can't price Premier Support from margin math alone, so I queue a conversation with whoever delivers it. For the tax-exempt term, I confirm the customer is still exempt, a check my Deal Strategy Assistant can run, and raise it with another team if the status has changed.

Helps answer:Legal, Finance, and ProductDeal flow efficiency

Clip 10 of 18 · 4:44

The first-round counter to Sales

The plan I'd bring to the AE: no deeper seat discount, and a 7% increase to $341.06 a seat if they drop to 225 seats for three years. Tiered pricing lets them grow into better rates, credits go to 91 cents (the same 7%), and overages stay at the committed rate. I open high, with room to work down.

This is my first-pass counter, built on the wrong annual figure. In Clip 14 I find the deal is about $2.28M a year, not $189K, and in Clip 17 I drop this approach.

Helps answer:Complex enterprise dealGive/get

Clip 11 of 18 · 2:03

Trade billing terms for price

Quarterly billing at net 60 is a big change from annual upfront. I ask what the customer values most, because billing flexibility can be a give if it buys a three-year commitment and healthy pricing. A tighter renewal cap is an easy give if the rest comes together.

Helps answer:Give/get

Clip 12 of 18 · 2:33

Rev Accounting, and how Sales hears a no

A three-year term and longer price protection go to Rev Accounting for approval. A refund request on a non-refundable contract is a clear no, and I coach the AE to say so plainly instead of leaving the door open. Sales feels more confident saying it when the no comes with internal backing.

Helps answer:Saying no to SalesLegal, Finance, and Product

Clip 13 of 18 · 1:56

Is November 6 real? Don't speed up for free

I would not expect this to close in 30 days. I ask whether anything actually forces a Nov 6 signature, such as a budget deadline or an approver. If there is real urgency, it may justify more gives. If not, the renewal date is the working deadline.

Helps answer:Saying no to Sales

Clip 14 of 18 · 4:47

Price the ask in a sheet, and catch my own mistake

I open a sheet and price what the customer wants next to what they pay today. The annual fees come out wrong: the $189K on the order form is a monthly number. Today's deal is about $4.55M over two years, $2.28M a year, and the ask takes about $800K a year off it. That is an unequivocal no, and rollover is a much cheaper give than a write-down this size.

Helps answer:Complex enterprise dealPrice analysis

Clip 15 of 18 · 1:47

Pick the deal apart, then check the margin

I skip the hand math and say what I would do next: take the deal apart one variable at a time, so every no has a reason behind it, then compare the margin on today's deal to the margin on the ask. SaaS runs about 85%, and I don't like to go under 80% outside of rare exceptions. I don't have a real price book in this demo, so I don't run it on camera.

Helps answer:Price analysisLegal, Finance, and Product

Clip 16 of 18 · 2:15

At this size it goes to leadership

A deal this big isn't just me. My game plan doesn't change, but I expect it to end up with the CFO and the head of sales, and a competitor bid that low is probably legit. I still take the first round of feedback through the rep so I have the context, and I lay the numbers out for leadership so they aren't digging for them.

Helps answer:Complex enterprise dealSaying no to Sales

Clip 17 of 18 · 2:07

I changed my mind. That's not capitulating

At this size I wouldn't even model a 7% increase, so the opening counter from earlier is out. My first read was built on the wrong annual fees. I read the math, found the mistake, and made a new judgment call. Being fluid and flexible matters on deals, pricing, and concessions.

Helps answer:Complex enterprise dealPrice analysisGive/get

Clip 18 of 18 · 1:27

Line up my manager and accounting before it moves

I get my manager aligned that a re-rate is on the table, along with the termination and price cap questions. Accounting comes in too. It isn't really a Rev Rec issue by itself, but it can be depending on how much discounting I give. We forecast the standard 5% to 7% increase on a renewal worth about $2.28M a year, and this dramatically reduces it.

Helps answer:Complex enterprise dealLegal, Finance, and Product

Deal Strategy Assistant

Start with the full walkthrough, or jump to a shorter clip. All data is fictional.

Demo video 1 · 10:50

Full walkthrough

The complete recording from start to finish: the Salesforce pipeline, the brief run in Claude, and the Slack draft.

Demo video 2 · 2:35

Run the daily brief

Claude runs the brief against the Salesforce pipeline and surfaces one deal that needs strategy help today: a new logo whose parent company already has a closed-won contract. The brief also lists what it has not confirmed.

Demo video 3 · 1:29

Slack draft, saved unsent

The message to the account executive arrives as an unsent Slack draft. The analyst reads it, edits it, and decides whether to send.

Demo video 4 · 1:51

The Salesforce pipeline

The demo Salesforce org the brief reads: the home page and the Opportunities list. All records are fictional.

Demo video 5 · 1:47

What the brief leaves out

The brief lists the deals it did not surface and why, including a bulk close-date update it did not treat as news, and the checks it skipped.

Demo video 6 · 1:04

More deals in the same run

Two more cards: a county health agency new logo with an open tax-exemption certificate question, and an expansion whose close date has slipped three times.

Demo video 7 · 0:56

Wrap-up

The closing segment, recorded back in the Salesforce pipeline view.

Interactive brief

This is a static export dated 2026-09-26, rendered from JSON. Deal facts come from a fictional Salesforce Developer Edition org; the recommendations and draft messages are authored examples. Amounts are total contract value (TCV), and days to close count from Sep 26. Select a deal to expand it. This page makes no Salesforce or Slack calls.

Deal Strategy Brief — Brennan Ward

2026-09-26
Open deals reviewed
40
Worth your time
5
Surfaced TCV
$2.98M
AEs covered
5

Connector and data warnings

  • Meeting-notes connector not connected: call summaries skipped.
  • Contract object was empty in this org on the as-of date: affiliate pricing was read from Account descriptions, not Contract records.
  • Owner.Manager is not set on User records: AE-to-manager routing came from the setup file, not Salesforce.
Filter:
  1. HIGHReach out today

    1. Halvorsen Energy — Expansion

    $450K TCV · Expansion · Negotiation/Review · closes 2026-09-29 (3 days from Sep 26) · AE Derek Olsen · Mgr Marcus Reyes

    Close date slippingNo deal strategy engagement
    Details

    What I see

    • Close date slipping. Close date pushed three times since July. Next Step reads 'Close this week'. Chatter, Sep 25: 'Budget approval slipped again. Customer says end of week.'Source: Opportunity Description, NextStep, FeedItem 0D5…Ee5
    • No deal strategy engagement. No open Deal Strategy case on Halvorsen Energy.Source: Case search

    Why it matters

    A deal that slips on budget sign-off three times may have a structure problem, not only a calendar problem. If the customer cannot fund the full expansion this quarter, a ramp or a split start date could let the paper sign now while spend lands when the budget does.

    Recommended next step

    Ask Derek what the budget approval is contingent on. If funding the full expansion at once is the block, offer a 90-day ramp on the new hosts so the order form can sign before the full amount is funded.

    Deal type basis
    Existing customer (Type = Existing Customer - Upgrade) and the opportunity name says Expansion; the amount adds hosts to an existing deployment.
    Sales tax
    No exemption signal in the record. Finance/Tax confirms treatment.
    Affiliates
    None found.
    Deal Strategy case
    None open

    Draft to Derek (authored example, unsent)

    Hi Derek, hope you're doing well. I noticed Halvorsen's close date has moved three times on budget sign-off, and the latest note says end of week. If the block is funding the whole expansion at once, a 90-day ramp could let the paper sign now while spend lands as they migrate, without changing the rate. This is simply a proactive suggestion for you to consider. I'm happy to model two options and talk them through over a 20-minute Zoom call this week. Let me know if you have any questions.

    Draft sources: Opportunity Description and NextStep (006…KE8Lg); Chatter post 0D5…Ee5, Sep 25

    Record: Opportunity 006…KE8Lg

  2. HIGHReach out today

    2. Pinecrest Software — New Logo

    $330K TCV · New Logo · Negotiation/Review · closes 2026-10-09 (13 days from Sep 26) · AE Priya Raman · Mgr Dana Whitfield

    Cloud marketplace routeSignature path mismatchNo deal strategy engagement
    Details

    What I see

    • Cloud marketplace route. Customer wants to buy through AWS Marketplace to burn down an EDP commitment. Chatter, Sep 25: 'Their cloud team says the private offer needs to be in by the 1st to count against this year's commit.'Source: Opportunity Description, FeedItem 0D5…Ee4
    • Signature path mismatch. Next Step is 'Finalize pricing'. No private offer, order form, or marketplace paperwork mentioned. The customer's deadline (Oct 1) is earlier than the close date (Oct 9).Source: Opportunity NextStep, Chatter (30d)
    • No deal strategy engagement. No open Deal Strategy case on Pinecrest Software.Source: Case search

    Why it matters

    A private offer has its own paper and its own clock. If it is not published by Oct 1, the customer may lose the EDP credit, and the deal could slip or come back asking for a discount to make up the difference.

    Recommended next step

    Line up the marketplace paperwork now: confirm the AWS account ID, the private-offer terms, and who signs. Move the internal target to Sep 30.

    Deal type basis
    Type = New Customer; the account has no earlier opportunities, contracts, or cases in the org.
    Sales tax
    Marketplace route: tax handling depends on the private-offer terms. Finance/Tax confirms.
    Affiliates
    None found.
    Deal Strategy case
    None open

    Draft to Priya (authored example, unsent)

    Hi Priya, hope you're doing well. I noticed Pinecrest's cloud team needs the AWS private offer in by the 1st to count against their EDP commitment, which is about a week before the Oct 9 close date. Starting the marketplace paperwork now (their AWS account ID, the offer terms, and the signer) could keep the deal on track. This is simply a proactive suggestion for you to consider. I'm happy to walk through it over a 20-minute Zoom call this week. Let me know if you have any questions.

    Draft sources: Opportunity Description and NextStep (006…KE8Lf); Chatter post 0D5…Ee4, Sep 25

    Record: Opportunity 006…KE8Lf

  3. HIGHReach out today

    3. Lakeshore County — New Logo

    $410K TCV · New Logo · Negotiation/Review · closes 2026-10-12 (16 days from Sep 26) · AE Maya Chen · Mgr Dana Whitfield

    Possible tax-exempt entitySignature path mismatchNo deal strategy engagement
    Details

    What I see

    • Possible tax-exempt entity. Account is Lakeshore County Health District: Industry = Government, Ownership = Other. Chatter, Sep 25: 'Procurement confirmed they need our vendor packet by end of month. Nothing on tax yet.' No exemption documentation is noted. Eligibility is not confirmed; it needs Finance/Tax review.Source: Account 001…NKw, FeedItem 0D5…Edz
    • Signature path mismatch. Next Step: 'Procurement reviewing order form'. Procurement asked for a W-9 and vendor packet. A public-sector purchasing review is not reflected in the close date.Source: Opportunity NextStep and Description
    • No deal strategy engagement. No open Deal Strategy case on Lakeshore County Health District.Source: Case search

    Why it matters

    Public-sector buyers often need vendor onboarding, tax documentation, and a purchasing review before they can sign. Each step can take time if it starts late (an assumption for this example: about a week each). Starting early protects the Oct 12 close date.

    Recommended next step

    Send Maya the vendor packet (including the W-9) and start the tax-documentation request with Finance/Tax today. Ask procurement whether a cooperative purchasing vehicle is required.

    Deal type basis
    Type = New Customer; the account has no earlier opportunities, contracts, or cases in the org.
    Sales tax
    Possible exemption (county health agency). Not confirmed, and no documentation is on file. Finance/Tax decides eligibility and required documents.
    Affiliates
    None found.
    Deal Strategy case
    None open

    Draft to Maya (authored example, unsent)

    Hi Maya, hope you're doing well. I noticed Lakeshore's procurement wants our vendor packet by the end of the month, and the Chatter note says nothing has moved on tax yet. If the county may qualify for a tax exemption, Finance/Tax will need to confirm eligibility and the documents required, so it may be worth starting that request alongside the vendor packet. This is simply a proactive suggestion for you to consider. I'm happy to help line it up over a 20-minute Zoom call this week. Let me know if you have any questions.

    Draft sources: Opportunity NextStep and Description (006…KE8LZ); Account 001…NKw (Industry, Ownership); Chatter post 0D5…Edz, Sep 25

    Record: Opportunity 006…KE8LZ

  4. MEDIUMMention this week

    4. Brightwater Logistics — New Logo

    $640K TCV · New Logo · Proposal/Price Quote · closes 2026-10-28 (32 days from Sep 26) · AE Maya Chen · Mgr Dana Whitfield

    Private equity ownershipAffiliate with pricing on fileMulti-year ask
    Details

    What I see

    • Private equity ownership. Account description: 'Portfolio company of Harborline Capital Partners, acquired 2024.' Harborline Capital Partners exists as an Account (Industry = Finance, private equity firm).Source: Account 001…NKt, Account 001…1ED
    • Affiliate with pricing on file. Ridgeway Haulage Co is also a Harborline Capital Partners portfolio company and a customer since 2024 (Closed Won, Dec 2024).Source: Account 001…NKu
    • Multi-year ask. Customer wants a 3-year deal; the CIO asked for the best multi-year rate. Next Step: 'Send proposal with 3-year pricing'. Chatter, Sep 25: 'CIO mentioned Harborline wants to standardize tooling across their other companies next year.'Source: Opportunity Description, NextStep, FeedItem 0D5…Ee0

    Why it matters

    A sponsor that wants to standardize tooling is a portfolio motion, not one deal. Pricing Brightwater against Ridgeway's paper and offering sponsor-level terms now may set the rate card for every portfolio company that follows, and Ridgeway is a possible reference.

    Recommended next step

    Before the 3-year proposal goes out, ask whether Harborline wants pricing that covers other portfolio companies. Structure the multi-year rate as a give against a sponsor-level commitment, not a standalone discount.

    Deal type basis
    Type = New Customer; the account has no earlier opportunities, contracts, or cases in the org. Built to demonstrate a PE-owned new customer whose portfolio affiliate is already a customer, with a multi-year ask.
    Sales tax
    No exemption signal in the record (private company). Finance/Tax confirms treatment.
    Affiliates
    Ridgeway Haulage Co (Harborline Capital Partners), customer since 2024.
    Deal Strategy case
    None open

    Draft to Maya (authored example, unsent)

    Hi Maya, hope you're doing well. I had a chance to review Brightwater Logistics and noticed it's part of Harborline Capital Partners' portfolio. Ridgeway Haulage is also in that portfolio and is already a customer, so it may be worth exploring whether the sponsor wants a coordinated approach before the three-year proposal goes out. I'm happy to help assess the options and structure a recommendation. This is simply a proactive suggestion for you to consider. Happy to discuss it over a 20-minute Zoom call this week if useful. Let me know if you have any questions.

    Draft sources: Account 001…NKt (Brightwater description: Harborline portfolio company); Account 001…NKu (Ridgeway Haulage: Harborline portfolio, customer since 2024); Opportunity NextStep: 'Send proposal with 3-year pricing' (006…KE8La); Chatter post 0D5…Ee0, Sep 25

    Record: Opportunity 006…KE8La

  5. MEDIUMMention this week

    5. Corvane Financial — Renewal (commitment reset)

    $1.15M TCV · Renewal · commitment reset · Qualification · closes 2026-11-03 (38 days from Sep 26) · AE Priya Raman · Mgr Dana Whitfield

    Reset or renewal approachingConsumption ahead of commitmentNo deal strategy engagement
    Details

    What I see

    • Reset or renewal approaching. Opportunity is a commitment reset. Next Step: 'Schedule renewal kickoff'. Stage is still Qualification 38 days out.Source: Opportunity NextStep, StageName
    • Consumption ahead of commitment. Consumption through month 9 is 138% of the prorated commitment, driven by log ingestion. Chatter, Sep 25: 'Log volume keeps climbing, customer is happy but finance is asking about the overage trend.'Source: Opportunity Description, FeedItem 0D5…Ee1
    • No deal strategy engagement. No open Deal Strategy case on Corvane Financial.Source: Case search

    Why it matters

    Sustained overage is a strong signal for a larger commitment. If the reset is sized from actual usage, the overage can become a bigger commitment at a better rate, and the finance conversation gets easier, not harder.

    Recommended next step

    Pull nine months of usage and model the run rate forward. Bring Priya three reset options (12, 24, 36 months) before the kickoff so the customer's finance team hears a plan, not an overage bill.

    Deal type basis
    Existing customer (account note: platform subscription since 2023). Next Step is 'Schedule renewal kickoff', so the primary type is Renewal; the commitment reset is the structure. The org's Type list has no Renewal value, so the type is carried in the name. If the reset is sized up from usage, it can also be read as an expansion.
    Sales tax
    No exemption signal in the record (public company). Finance/Tax confirms treatment.
    Affiliates
    None found.
    Deal Strategy case
    None open

    Draft to Priya (authored example, unsent)

    Hi Priya, hope you're doing well. I noticed Corvane is running at 138% of its prorated commitment on log ingestion, and their finance team is already asking about the overage. Sizing the reset from actual usage could turn the overage into a larger commitment at a better rate, which may make for an easier conversation. This is simply a proactive suggestion for you to consider. I'm happy to sketch the options with you over a 20-minute Zoom call this week, before the kickoff. Let me know if you have any questions.

    Draft sources: Opportunity Description and NextStep (006…KE8Lc); Chatter post 0D5…Ee1, Sep 25

    Record: Opportunity 006…KE8Lc

Also watching

  • Oakridge Mutual — New Logo (tool consolidation) ($760K TCV)
    Not surfaced in this run: the brief shows at most five deals, and five ranked higher. Flags: tool consolidation (three tools being replaced; two of the customer's contracts end in March, one next September) and a 45% discount request. No Deal Strategy case is open. A phased ramp could answer the 'can't pay for both' concern without the discount. Because it was not surfaced, it is eligible again in the next brief.
  • Tallis Retail — Expansion ($520K TCV)
    Not surfaced in this run: ranked below the five surfaced deals. Flag: early non-standard asks (a 5-year price lock and termination for convenience after year 2) raised in Chatter, with no Deal Strategy case open. Because it was not surfaced, it is eligible again in the next brief.

Already engaged (not surfaced)

  • Lumenfield Media — Renewal ($380K TCV)
    Deal Strategy case 00001026 is open (ramp structure). Chatter: 'Thanks for the ramp model, sending to customer today.' Rule: a deal with an open Deal Strategy case is not surfaced; it is listed here instead.

Checks skipped

  • Meeting notes (connector not connected)
  • Contract records (none in this org on the as-of date)
  • Manager routing from Salesforce (User.Manager not populated)

Coverage: Maya Chen, Derek Olsen, Priya Raman, Luis Ortega, Hannah Brooks. Managers: Dana Whitfield, Marcus Reyes. Deal-support rule: Open Case with Subject starting 'Deal Strategy -' linked to the Account. Minimum TCV reviewed: $25,000. The brief shows at most 5 deals and skips deals raised in the last 21 days unless something material changed.