Shopify Sidekick + subscriptions, end to end

What Shopify Sidekick is

Sidekick is the conversational AI assistant Shopify launched in 2024 and now ships in the top-right corner of every Shopify admin page. Out of the box it understands the native Shopify domain — products, orders, customers, themes, discounts — and can take small admin actions on your behalf (create a discount, edit a product description, summarise a customer's orders). It's free, included on every Shopify plan, and turns on automatically for stores in supported regions.

The piece that matters for subscriptions is the App Extensions API. In late 2025 Shopify opened Sidekick to third-party apps: an installed app can register data tools that Sidekick is allowed to call when a merchant's question matches the tool's domain. The merchant types or speaks a question, Sidekick decides which tool to call, the tool queries the app's database in milliseconds, the result comes back as structured data, and Sidekick reads it back in plain English. The merchant never sees a tool name or a JSON payload — they just see an answer.

SimpleSubscription is the first subscription app on Shopify to ship a Sidekick extension. Recharge, Loop, Skio, and Bold have not. That means today, if you ask Sidekick "what's my subscription MRR?" on a store running any of those apps, you'll get a polite "I don't have access to that data." On a SimpleSubscription store, you'll get the number — with a per-currency breakdown if you have one, and a month-over-month change figure in context.

Why route subscription questions through Sidekick at all

The honest answer: you don't strictly have to. The SimpleSubscription dashboard shows the same data Sidekick reads, and for any deep analysis (cohort drill-downs, exporting data, configuring billing logic) you'll still open the dashboard directly. Sidekick isn't a dashboard replacement. It's a friction remover.

The practical change is the questions you actually get answered. Most operators have a vague sense that they "should look at MRR more often" but never do, because pulling up a dashboard, picking a date range, and reading three charts takes long enough that the lookup doesn't feel worth the effort. Asking Sidekick takes three seconds. So you check daily, catch problems earlier, and act on real numbers instead of intuition. The same shift happens for churn risk: rather than waiting for the monthly retention export, a Premium-plan merchant asks "who's at risk this week?" on Monday morning and reaches out to those three or four subscribers personally. That kind of human touch is where subscription businesses actually win.

• Three-second answers instead of three-click dashboard lookups
• Asked from the admin page you're already on — no context switch
• Voice or text input — works hands-free while you're packing orders
• Combines multiple data sources in one answer ("who's at risk AND hasn't ordered in 30 days")
• Reads aloud — useful when you're between meetings or on the move

The questions Sidekick can answer today

SimpleSubscription's Sidekick extension currently exposes twelve data tools that cover the core operational questions a subscription store asks every day. The tools are invoked by Sidekick automatically — you don't type a tool name, you ask in plain English and Sidekick picks the right one. Here's the catalog, grouped by the kind of question that triggers each one.

Performance and health questions — "What's my MRR?", "How are we doing this month?", "What's my churn rate?", "How many active subscribers do I have?". These hit the metrics tool and return MRR (with per-currency breakdown if multi-currency), 30-day rolling churn, active/paused/cancelled/expired/failed counts, and billing success rate. Available on every plan.

Lookup questions — "Find Sarah's subscription", "Show me everything for customer ID 12345", "What's in subscription contract gid://...". These hit the customer-lookup and contract-detail tools. They return the contract lines, the billing history, the next renewal date, and the churn risk score. Available on every plan.

Operational urgency questions — "Who hasn't paid this week?", "What's renewing tomorrow?", "Show me recent activity", "What failed billing do I need to recover?". These hit the failed-billing, upcoming-orders, and recent-activity tools. They return live lists with names, amounts, and Shopify-admin deep links so you can click straight from the Sidekick answer into the customer record. Available on every plan.

Strategic questions — "Who's at risk of churning?", "How are my March cohort doing?", "What product is driving the most MRR?", "How is the winback campaign performing?". These hit the churn-risk, cohort-retention, product-performance, and winback tools. Some are Pro-tier, some are Premium-tier — see plan-tier gating below.

Read-only by design — what Sidekick will NOT do

This is the section to read before you install. SimpleSubscription's Sidekick extension is pure read access. It answers questions but cannot change anything in your store. That's not a feature gap — it's an intentional safety boundary, and we think it's the right default for an AI-driven interface to subscription data.

Concretely, Sidekick cannot pause a subscription, cannot cancel one, cannot refund an order, cannot change a billing date, cannot edit subscription contract lines, cannot send a winback email, cannot trigger a manual billing attempt, cannot update a customer's payment method, and cannot adjust pricing. Every one of those actions still happens through the merchant dashboard or the customer portal, where there's a confirmation step, an audit trail, and a clear undo path. If you ask Sidekick "please pause Sarah's subscription," it will tell you it can't, and it will point you at the dashboard URL where you can do it yourself.

Shopify's own action-tool framework supports writes that go through a merchant-facing confirmation modal, and as that framework matures we may expose narrow, high-confirmation actions ("pause this exact subscription for two weeks — confirm?"). The current intent-category list doesn't include "subscription" as a supported action category yet, so the read-only posture matches Shopify's own roadmap. If you want destructive actions now, you do them in the dashboard.

• Cannot pause, cancel, or resume a subscription
• Cannot refund, void, or modify any order
• Cannot change billing dates, intervals, or pricing
• Cannot edit subscription contract lines (add/remove products)
• Cannot send emails, trigger campaigns, or push notifications
• Cannot update payment methods or trigger manual billing
• Cannot create, edit, or delete selling plans

The operator workflow — three scenarios where it earns its keep

Theory is easy. Here are the three concrete workflows where Sidekick replaces actual dashboard time for operators running subscription stores.

Monday morning health check. Open the Shopify admin, click Sidekick, ask "how are subscriptions doing?". You get MRR with month-over-month change, active subscriber count, 30-day churn rate, and billing success rate in one paragraph. If anything looks off, follow up with "why is churn up?" and Sidekick will pull recent cancellations with reasons. Five minutes instead of fifteen.

Failed-payment recovery, Wednesday afternoon. Ask "who hasn't paid this week?" — you get a list of failed billing attempts in the last seven days with the customer name, the amount, the failure code (insufficient_funds vs. card_declined vs. authentication_required), and a deep link to each subscription in the admin. For the 3DS-pending ones you can email the customer a one-line nudge with the portal link. The whole loop is about ten minutes for a store with twenty failed attempts; the alternative is exporting a CSV from the dashboard, sorting it, and writing a separate email template.

Friday churn-risk outreach (Premium plans). Ask "who's at risk of churning this week?". Sidekick calls the churn-risk tool, which returns the top ten subscribers ranked by AI-scored risk along with the reason (e.g. "opened cancel page twice this week", "skipped last two renewals", "failed billing twice this month"). You pick the two or three accounts you actually want to save, draft a personal email, and you're done in fifteen minutes. Reduce subscription churn covers what to actually say in those emails — Sidekick gets you the right list.

How insights are ranked — live data, not generic AI

There's a category of AI-product disappointment that goes "I asked the AI a question and it gave me a confident, plausible, and wrong answer." That's hallucination — the model invented numbers because it didn't have real data. Sidekick avoids this for subscription questions because every answer is grounded in a live tool call against your actual database. No model is asked to estimate; the tool returns the structured number and Sidekick reads it back.

For strategic questions — "how do I grow MRR?", "who's at risk?" — the ranking comes from SimpleSubscription's own scoring logic, not from the model's judgement. Churn risk uses a feature set (payment failure history, recent portal activity, time since last skip, contract age, cancellation flow interactions) and assigns a numeric risk score per subscriber. Sidekick reads the top of that ranked list. The model picks the words; the data picks the ranking.

This matters because the failure mode of pure-LLM analytics is plausible-but-wrong recommendations. When a model is asked to rank churn risk based only on natural-language context, it tends to surface dramatic-sounding cases over actually-risky ones. Grounding the ranking in deterministic scoring logic — and only letting the model paraphrase — keeps Sidekick honest.

Plan-tier gating — what's in each plan

Some tools are available on every plan including the 90-day free trial; some require Pro; two require Premium. The gating is enforced server-side — Sidekick simply won't see a paid tool's output for a lower-tier shop, and the merchant gets a polite upgrade hint instead of a confusing error.

Every plan (including free trial): MRR with per-currency breakdown, churn rate, active subscriber counts, billing success rate, failed billing attempts, upcoming orders, recent activity, customer lookup, contract details, and active subscription listing. The everyday operator questions all work on day one of the free trial — you can install, ask Sidekick "what's my MRR?" and get the answer immediately.

Pro plan: cohort retention (signup-month buckets with retention curves), winback campaign performance, and loyalty program summary. These are the analytical tools you reach for once you have enough subscribers (a few hundred plus) for cohort-level signal to matter.

Premium plan: churn risk predictions (per-subscriber AI-scored risk list) and product performance (top products by active subscribers and MRR). These are the heavier compute-cost tools — the churn model runs nightly and stores a score per subscriber, the product performance tool runs an aggregation across the full subscriber base.

Multi-currency and Shopify Markets

Multi-currency reporting is one of the places where Sidekick most clearly outperforms a generic dashboard. A merchant running on Shopify Markets often has active subscriptions in three or four currencies — say EUR, USD, GBP — and the wrong answer is to silently sum them in the store's primary currency at today's exchange rate. That number is meaningless (and wrong by tomorrow).

SimpleSubscription reports MRR in two ways. The first is a single top-line figure in the shop's primary currency — useful for dashboards that need one number to show. The second is a per-currency breakdown for shops with active subscriptions in multiple currencies. Sidekick knows about both. Ask "what's my MRR?" on a single-currency shop and you get the simple number. Ask the same question on a multi-currency Markets store and Sidekick will tell you the breakdown is mixed and read each currency separately: "You have €4,200 MRR in EUR, $5,800 in USD, and £1,100 in GBP."

• Primary-currency MRR is the field a single-number dashboard uses
• Per-currency MRR is the field Sidekick reads aloud when currencies are mixed
• An mrrMixedCurrencies flag tells Sidekick to frame the answer correctly
• No silent FX conversion — currencies are reported as collected, not converted
• Same pattern applies to failed-billing volume and upcoming-order totals

Privacy and data scope

When Sidekick calls a SimpleSubscription tool, the call is scoped to your shop only via a signed session token from Shopify. There's no cross-tenant access, no "read other stores' data", and no Sidekick-side persistence of your subscription data after the conversation ends. The data flow is: merchant question → Sidekick → tool API call → SimpleSubscription database (your shop's records only) → structured response → Sidekick reads it back.

What Sidekick reads is what your dashboard already shows — subscription contracts, billing attempts, customer email and name on a contract, churn score, upcoming-order schedule. We don't expose anything Sidekick wouldn't see by looking at your dashboard manually. We don't expose payment method details (no card numbers, no CVV, no full tokens — only the last 4 digits and card brand that Shopify itself exposes). We don't expose customer addresses in tool responses unless the question is specifically a contract-detail lookup that needs the shipping address to answer.

On the Sidekick side: Shopify's documentation says Sidekick conversation history is stored for the merchant's own admin recall, not used to train models on subscription data, and not shared across stores. Sidekick is built into the Shopify admin, so the data-handling posture is whatever Shopify's own admin-data posture is — refer to Shopify's privacy documentation for the canonical answer.

Limitations and known edge cases

Sidekick is good at fast answers; it's not a substitute for the dashboard for everything. Here's the candid list of where it falls short, so you know to switch to the dashboard for these.

• No destructive actions — by design, see read-only by design
• No FX conversion — multi-currency MRR is reported per-currency, never converted
• No scheduled reports — Sidekick is conversational, not a cron job. For scheduled exports, use the SimpleSubscription dashboard's CSV export or the public REST API
• No deep historical drill-down — questions are answered against current state plus recent history. For "what was MRR on March 14, 2024?" you'll want the dashboard's date-range filter
• No cross-app correlation — Sidekick can read SimpleSubscription data and native Shopify data, but it can't cross-reference data from another third-party app you might have installed
• No file uploads — you can't paste a CSV of subscriber IDs and ask Sidekick to look them all up. The lookup tools take one customer at a time
• Response budget — each tool has a 1-second budget. For very large stores (10,000+ active subscribers) some aggregation queries may degrade; the dashboard's longer-running export is the right fallback

None of these are deal-breakers for the operator workflow. They're the lines between "ask Sidekick" and "open the dashboard" — and once you've used the extension for a week you stop thinking about which side any given task falls on.

Getting started

There's no separate Sidekick setup. Install SimpleSubscription from the Shopify App Store and the Sidekick extension auto-registers during the standard OAuth flow. The next time you open Sidekick in the admin and ask a subscription question, Shopify routes the call to our tool automatically. No config file, no API key, no extra permissions popup.

If you're switching from Recharge, Loop, Skio, or Bold, the migration is free and preserves your existing subscription contracts — including billing dates, payment methods, and discount history. Sidekick lights up the day the migration completes. The hardest part of the extension is asking the first question; after that the workflow finds you.