Upsell opportunity brief
Use this skill before a review or check-in with an existing client, or when a project is weeks from ending and nothing has been lined up after it. Produces a one-page brief: the one opportunity worth raising, the evidence from delivery that supports it, the price, who signs, and the sentence to open with. Also use for "what else can we sell [client]", "prep the renewal conversation", "this project ends next month", "expansion opportunities in the book".
Jay DingwallCEO and Founder, FamousFolksApplies to a client already paying, before a review or at the end of a project. Produces one page naming a single opportunity and the proof from the work itself.
The play
- Start in the delivery record, not the service list. What the team actually did, worked around and absorbed is where real expansion lives. Reading the service list first produces a pitch for whatever the firm most wants to sell, which the client can hear coming. The sources, in order of how well they convert, are in references/signal-sources.md.
- Pull the free work first. Everything delivered this quarter that was not in scope and was not billed. On most accounts this is the entire brief: the client already values it, already receives it, and is already not paying for it. Converting it is a pricing conversation, not a pitch.
- Add what the team worked around. A thing the delivery team keeps patching is a problem the client has, whether or not they have named it.
- Add what the client asked for and did not get quoted. Asked once is a note, asked twice is an opportunity, asked three times and not quoted is a failure of account management.
- Run the gates before writing anything. Account health, a named problem in the client's own words, a budget holder, and timing. All four, in that order, with the failure conditions in references/qualifying-gates.md. The first gate is the one that matters: an unhealthy account is never upsold, it is fixed.
- Pick one opportunity. Not three with a recommendation, one. A brief listing options moves the decision back onto the client, and an unhappy or busy client declines all of them.
- Branch by the situation:
- Project ending, delivery went well: lead with continuation, priced as a retainer, raised at least six weeks out. Four weeks is already late.
- Project ending, delivery was rocky: no expansion. Close well, fix the relationship, revisit next quarter.
- Retainer running steady: convert the free work. Nothing new, just scope and price catching up with reality.
- Champion has changed: the new person did not buy the original work and owes it nothing. Re-establish value before proposing anything.
- Client raised budget pressure in the last quarter: the only sellable opportunity is one that removes a cost they have already named.
- Write the brief to the format in references/brief-format.md, including the one sentence that opens the conversation. Draft that sentence before the price, because an opportunity that cannot be opened in one sentence is not clear enough to sell.
What good looks like
- First thing I check that most people skip: how much unbilled work went out the door last quarter. The biggest expansion on most accounts is already being delivered free, and nobody has counted it.
- The mediocre version: a list of every other service the firm offers, mapped to the client with no evidence, raised at the renewal meeting because that is when somebody remembered. The client hears a vendor trying to grow an account.
- I know the brief is right when the opening sentence quotes something the client said and the opportunity sounds like their idea.
- Second test: it names who signs, and that person has been in a room with the firm this quarter. If they have not, the real work is getting access, not writing a proposal.
- Red flag: the evidence section cites the firm's capability rather than the client's situation. That is a brochure.
Rules
- MUST run the health gate first and stop there when it fails.
- MUST base the opportunity on evidence from delivery, quoted where possible.
- MUST name one opportunity, not a menu.
- MUST name the signer and when they were last engaged.
- MUST raise an end-of-project continuation at least six weeks out.
- NEVER upsell an account with unresolved delivery problems.
- NEVER lead with a service the client has not given a reason to need.
references/brief-format.md
The brief
One page, internal. Read before the meeting, never sent to the client.
[CLIENT] - upsell brief - [date]
Current: [what they pay, for what, since when]
Health: [pass] - [one line of evidence]
THE OPPORTUNITY
[One sentence. What the firm would do and what it changes for them.]
THE EVIDENCE
- They said: "[verbatim, with who and when]"
- We delivered [X hours / N instances] of this outside scope last quarter
- The team has worked around [specific thing] on [N] occasions
THE PRICE
[Number and shape: retainer, project, rate change. One option.]
WHO SIGNS
[Name, role. Last in a room with us: [date]. Knows our work: yes/no.]
WHEN
[Date to raise it, and the meeting it belongs in.]
THE OPENING LINE
"[The one sentence that starts the conversation.]"
IF THEY SAY NO
[The one thing to learn from the no.]
The opening line
Drafted before the price. Three properties:
- It quotes or paraphrases something the client said.
- It describes their situation, not the firm's service.
- It can be said out loud without a deck.
| Weak | Strong |
|---|---|
| "We wanted to talk about expanding our scope." | "You mentioned the team can't keep up with landing pages. We've built nine for you outside scope this quarter. Can we talk about making that part of the engagement?" |
| "We have a design system offering." | "Every new page takes us three rounds because there's no component library. Want me to price fixing that once?" |
If the sentence cannot be written, the opportunity is not understood well enough to raise.
One option, not three
A menu transfers the decision back to the client, and a busy client declines a menu. Pick the one with the best evidence behind it and hold the others for next quarter.
The exception is price shape, not substance: the same opportunity as a project or as a retainer is one option with two ways to pay.
If they say no
Fill this in before the meeting. The useful nos are specific: not now, not that, not at that price, not me who decides. Each points somewhere different, and deciding in advance what to listen for turns a declined pitch into account intelligence rather than a bad afternoon.
What never goes in
- Capability descriptions. The client knows what the firm does.
- Case studies from other clients. This brief is about their evidence.
- More than one opportunity.
- Anything the delivery team has not confirmed. A brief built on an opportunity the team cannot staff is worse than no brief.
references/qualifying-gates.md
The gates
Four, in order. A failure at any gate stops the brief. Writing one anyway produces a conversation that costs more than the work was worth.
Gate 1: account health
Fails if any of these is true:
| Condition | Why it stops everything |
|---|---|
| A delivery problem raised in the last 60 days and not closed out | Expansion reads as a firm that would rather sell than fix |
| A missed deadline this quarter with no reset conversation | Same |
| An invoice more than 30 days overdue | They have a reason they have not mentioned |
| Response times from the client doubling over a quarter | Disengagement. Find out why first. |
| The last three meetings were status, with no decisions | The relationship has gone transactional |
A failed health gate is not a delay, it is a different piece of work. Fix the account, then revisit next quarter.
Gate 2: a named problem
The opportunity must answer something the client has said, in words that can be quoted back. Not inferred, not something the firm believes they need.
Passes: "Our team can't keep up with the volume of landing pages." Fails: "They'd really benefit from a design system."
If nothing qualifies, the gate failure is the finding: the firm does not know enough about the client's current problems, and the next conversation is discovery, not a proposal.
Gate 3: a budget holder
Name the person who signs. Then answer two things: have they been in a conversation with the firm this quarter, and do they already know what the firm delivers.
| Situation | What to do |
|---|---|
| Signer engaged this quarter | Proceed |
| Signer exists but has not been engaged | The opportunity is access. Get in a room first. |
| Day-to-day contact says they will handle it internally | Help them sell it. Give them a one-pager in their language, not yours. |
| No signer identified | Stop. This is the whole problem. |
Gate 4: timing
| Trigger | Raise it |
|---|---|
| Project ending | At least 6 weeks before the end |
| Retainer renewal | 8 weeks out |
| Free work conversion | At the next scheduled review, never ad hoc |
| Problem the client just named | Within 2 weeks, while it still hurts |
| Client in budget season | During planning, not after |
Fails if the only available moment is the renewal meeting itself. A first expansion conversation held in the renewal conversation makes the renewal harder, because it turns a decision about continuing into a negotiation about more.
When a gate fails
Write one line on which gate and what would clear it, and put it where the next quarter's brief will find it. A failed gate is useful information about the account, and it is lost every time someone just quietly decides not to pitch.
references/signal-sources.md
Where the signals are
Ranked by how often they turn into signed work. The order is the opposite of where most firms look.
1. Unbilled work already delivered
Everything done this quarter that was not in scope. The extra round, the deck that was not quoted, the "quick favour" that took two days, the person cc'd on everything who is not on the contract.
Converts best because there is nothing to prove. The client already receives it and already values it. The conversation is about the scope catching up with reality, not about buying something new.
Count the hours before the meeting. "We delivered about 60 hours outside scope last quarter" is a different conversation from "we've been doing a bit extra".
2. What the team works around
Anything the delivery team patches repeatedly. A broken handoff, a file the client never sends on time, a system nobody owns, a step done manually every month.
The client may not have named it. The brief's job is to name it in their terms and in hours or money, not to describe the workaround.
3. Asked for and never quoted
Requests that came up in a call and got a "we could look at that" and nothing else. Once is a note. Twice is an opportunity. Three times with no quote is a failure of account management, and the brief should say so internally even if it does not say so to the client.
4. Their stated plans
Something the client said they are doing next quarter that the firm could do or support. Hiring, a launch, a funding round, a conference, entering a new segment.
Weaker than it looks, because plans slip and the client knows their plans better than you do. Good as the timing hook for an opportunity from sources 1 to 3; thin as the opportunity itself.
5. Usage and results data
What the work produced, and where the numbers stopped. Useful as proof inside a brief built on something above, rarely enough on its own.
6. The firm's service list
Last. This is the source most briefs start from, and it is the reason most upsell conversations sound like a vendor growing an account. Use it only to put a name and a price on an opportunity the first five sources already found.
Collecting this without a research project
Fifteen minutes with the people who do the work, once a quarter, two questions:
- What did we do for them that we did not bill for?
- What do you keep having to fix or work around on this account?
Delivery teams answer both instantly. They have never been asked.