How Automated Upsells Increased Our AOV by 40%

If you're only selling one thing per transaction, you're leaving money on the table. The best time to make a second sale is immediately after the first — and with a little automation, this can happen without lifting a finger.

Here’s how we used simple code and automation tools to add strategic upsells that increased our average order value (AOV) by over 40%.

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Step 1: Identify the Natural Next Step

We started by mapping each service and product to its logical companion. Ask:

• What’s the natural next step after this purchase?
• What do successful clients buy next?
• What complements the current offer without overwhelming the customer?

Example:

• If someone books a website audit → offer a one-time implementation sprint
• If someone buys a digital product → offer a VIP support package or 1:1 consult

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Step 2: Build Smart Offer Logic

We used a combination of tools and code to make our upsells dynamic and automatic:

Tools:

• Stripe + Webhooks – to listen for successful payments
• Airtable – to store customer purchase history
• Make (Integromat) – to handle conditional logic and deliver upsells
• Email Tool (ConvertKit / ActiveCampaign) – for timed upsell campaigns

Automation Example:

• When a customer buys Product A, Stripe fires a webhook
• Webhook triggers Make scenario: checks Airtable for past purchases
• If Product B not yet purchased → send custom email with time-limited upsell

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Step 3: Insert Offers at Key Points

On Checkout:

• Use conditional logic to show upsells in-cart or post-checkout (e.g. "Add 1-on-1 onboarding for $99")

In Confirmation Email:

• Insert dynamic content based on what they bought.
  “Most buyers of [X] also get [Y] — available for 72 hours only.”

Via Follow-Up Sequences:

• Email 24–48 hours after purchase with testimonials or bonuses for upgrading

Code Tip: Use JavaScript to detect buyer segments and dynamically render offers on the confirmation page or account dashboard.

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Step 4: Make the Offer Irresistible

We tested upsells with:

• Urgency: timers and expiring links
• Scarcity: “Only 5 onboarding spots available this month”
• Value stacking: “Normally $299, today only $149 for buyers”

Result: When urgency and relevance aligned, conversions on upsells tripled.

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Results Snapshot

We didn’t increase traffic. We just captured more value from the traffic we already had.

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What Made It Work

• No human effort — the entire flow ran on autopilot
• Hyper-relevance — offers matched the buyer’s intent
• Timed logic — created urgency without pressure

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Want Our Automated Upsell Framework?
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