v1.3.03 loop iterations

Retainer Upsell Playbook

Acquiring a new client costs many times more than growing an existing one, yet most agencies spend almost no structured effort on expansion. The Retainer Upsell Playbook finds the natural expansion inside a current account, builds the case using the client's own data, and writes the conversation so it lands as strategic advice rather than a pitch.

What this skill does

The best upsell is advice, not sales. If the conversation feels like you're pushing product, it's lost before it starts. If it feels like you're pointing out something you noticed in their numbers, you've earned the right to recommend the next step. The GROW framework structures the brief so the conversation lands the second way.

Gap analysis comes first — what are they trying to achieve that the current scope doesn't fully address, and what's the logical next step from work you're already doing well. Results evidence builds the case from the client's own data, not from your service catalogue. Opportunity framing picks one of four shapes (the multiplier, the missing piece, the next level, the protection) so the recommendation has structural clarity rather than reading like a list of capabilities. Win-win proposal lowers the friction — pilot period, phased approach, small expansion to the existing retainer rather than a separate proposal that has to clear a separate approval.

The skill refuses to upsell unhappy clients. If the relationship is strained, the upsell conversation accelerates churn — the client reads the expansion attempt as "they're trying to make more money from a service that isn't even working." The opening question is always "how would you rate this client's satisfaction right now, one to ten?" Below seven, the skill produces a relationship-repair plan first and tells you to come back to the upsell after the next quarter's data lands.

You get the opportunity summary, the evidence section built from the client's own performance data, a proposed expansion with service, investment, projected impact, and timeline to results, the conversation framework (opener, insight, recommendation, easy-yes structure), objection handling for the three responses you'll actually hear ("we want more from current work first," "budget's tight," "let us think about it" — including a specific follow-up plan, not just a comeback), and a checklist of supporting materials to pull together before the conversation. The "small expansion to current retainer" framing is preferred over a separate £5K proposal, because it converts.

When this triggers

·You can see the gap in a client's setup but every framing you've tried for raising it sounds salesy
·You just delivered a strong quarter and want to convert the trust into a scope expansion rather than letting it dissipate
·You're trying to grow revenue without taking on more clients
·A client's stated goals don't match their current retainer scope and you want to surface that honestly
·You need the objection responses ready before the conversation, not after it

Example

Trigger

User: 'Content marketing client, £3K/mo. Blog ranking great — organic traffic up 60% in Q2. Their stated goal is trial signups but we don't touch the funnel below the blog. Want to propose a CRO add-on without it feeling pushy.'

Output

# Upsell brief — [Client] Current retainer: £3K/mo · Proposed: +£1,800/mo for 6 weeks pilot Opportunity summary: Blog traffic is up 60% but trial signups grew only 8%. The leak isn't above the funnel — it's between the blog and the trial form. A short CRO sprint focused on the five highest-traffic posts is the obvious next step, and it's the work that converts the SEO win into the metric they actually care about. The evidence (from their own data): · Top 5 blog posts: 42K monthly visits, 1.8% trial conversion · Same posts, paid landing variant: 6.4% trial conversion · Implication: ~£28K/yr trial value left on the table Proposed expansion: Service: CRO sprint — 5 highest-traffic posts, hypothesis testing, in-page conversion optimisation Investment: +£1,800/month for 6 weeks (pilot) Projected impact: 2-3x trial conversion on those five pages Timeline to results: 4-6 weeks Conversation framework Opening (after sharing Q2 results): "Looking at the Q2 numbers, the SEO work is doing exactly what we hoped — but I noticed something I want to flag. Your top five posts are pulling 42K visits a month and converting at 1.8%. The paid landing variants convert at 6.4%. We're leaving a meaningful chunk of the trial value on the table." The recommendation: "I'd like to propose a six-week CRO sprint on those five posts specifically. Same retainer rhythm, smaller add-on, focused output. If it lifts conversion the way we think it will, we'd fold it into the ongoing scope. If not, we stop after six weeks." Easy yes: Six-week pilot, defined exit, +£1,800/mo not a separate proposal. Objections: · "We want to see more from current work first" — current work is what surfaced the opportunity. Six-week pilot reduces the ask. Worth running parallel. · "Budget's tight" — pilot first, redirect from current spend if needed. Don't expand if relationship isn't healthy.

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What you get

134-line SKILL.md, ready to drop into ~/.claude/skills/
Tested through 3 Karpathy-loop iterations (versions v1.0.0 → v1.3.0)
Triggers automatically when relevant — no command to remember
Lifetime updates as the skill is refined further