Hello, Huan, thanks for connecting! I am Doornie, your personal AI sales buddy and cannot wait to chat w/ you.

How may I help you today? We can collaborate on formulating marketing or sales strategies or we can practice talking points. Just let me know what you'd like to do!

I’d be happy to work with you on strategies to engage inactive customers.

To form a strategy, let's first check the current status first. I have taken the liberty to retrieve a list of total 30 inactive customers from the database, and also conducted segmentation to help diagnose why they are not actively using our solution. This information can help us come up with targeted sale strategy to re-engage our inactive customers.

Below you can find the segmentation analysis based on our customers' inactivity, along with brief description including our targeted strategy to close the sales gap

• Light/partial use (still some activity but not habitual): fix gaps + expand
• Sustained decline (31–90 days + big drop): value erosion or slow adoption failure
• Recent drop-off (≤30 days since last trace + big usage drop): likely a change event (deploy, agent change, billing change, org change)
• Long dormant (>90 days): re-onboarding + requalification needed

Now which segment do you want to tackle first?

Great choice. Focusing on the Recent Drop-off segment gives us the highest probability of success.

Here are the principles we’ll use to guide the re‑engagement strategy for this group:

- The customer was using the product recently, so intent and familiarity still exist.

- Muscle memory is intact and their technical architecture likely hasn’t changed.

- The drop-off is usually caused by a trigger event such as a deployment change, configuration issue, billing update, or ownership change rather than a rejection of value.

- This creates a short feedback loop where the root cause is easier to identify.

- Quick wins are possible with minimal political or organizational friction.

- When addressed promptly, recovery rates for this segment are typically high. [AI synthesized]

Now, let’s define success together. When you say ‘engage inactive customers,’ what specific outcomes do you have in mind? For example, you want them to renew their existing license, enter into a new license agreement, or expand on their existing license agreement (e.g., upsell)?

Let’s explore the relevant data a bit more. I have made some analyses to highlight their last use of their license before they became inactive.

Based on this, can you describe any patterns you’ve seen among the inactive restaurants or could recall the situations that might have triggered their behavior change? For example, did they stop engaging after a price change in DoorDash marketplace, a feature release, or a season?

That’s totally fine — I can help surface a pattern from the data.

Looking at the dataset, the primary driver of Storefront under‑usage doesn’t appear to be dissatisfaction with the commission‑free model or merchants switching to a competitor. Pricing doesn’t show up as a signal here. Instead, the drop‑off is largely tied to merchant‑initiated operational changes, especially cases where online ordering was paused or the website widget was disconnected. This points more toward operational disengagement or traffic/configuration issues rather than a value rejection.

One thing that stands out is timing: most of the last recorded activities cluster around August and September. Does that period ring a bell for you? For example, was there a seasonal shift, an operational change, a staffing or ownership change, or any rollout or policy update around that time that might have prompted merchants to pause online ordering or adjust their website setup? [AI synthesized]

Anything you could think of or recall would be very helpful.

Let’s think deeper — any additional causes that might lead to their inactivity if you can think of? More importantly, which ones do you think your team can realistically influence?

Great — since upgrade-related incompatibility is the core issue and free troubleshooting is something your team can control, let’s translate that into concrete strategic levers.

Thinking about re‑engaging these recent drop‑off restaurants and driving renewal, what levers do you want to pull around the following areas?

For example:

- Outreach approach: how do you want to reach them (CS-led calls, email, in‑product messages), and how proactive or high‑touch should it be?

- Value framing: how will you position the outreach so it feels helpful rather than sales‑driven (e.g., “post-upgrade health check,” “compatibility audit”)?

- Incentives or risk removal: are there any short-term incentives you’d consider pairing with troubleshooting (temporary fee relief, service credits, extended trial time)?

- Product or operational support: what level of troubleshooting or configuration help can you realistically offer, and how fast?

- Renewal pressure vs goodwill: do you want to tie this explicitly to renewal, or first focus purely on restoring usage and trust?

Which of these levers feel most realistic and impactful for your team to activate first? [AI synthesized]

Could you share with me your best idea (just one) so we can work together to turn them into a testable hypothesis? I'd love to help you frame it in a way that fits your situation. I'd love to see you frame your ideas in the following hypothesis: "If we do XYZ, it will help those customers..."

How does that sound to you?

That’s perfectly fine — what you outlined already makes a lot of sense and is a strong foundation to work from. Let me help you crystallize it into a few clear, testable hypotheses.

- **Hypothesis 1 (Core play):** If we proactively reach out to recent drop‑off restaurants with a CS‑led “post‑upgrade health check” and offer free troubleshooting to resolve compatibility issues introduced in the Aug/Sept Storefront upgrade, it will restore paused ordering activity and increase the likelihood of license renewal.

- **Hypothesis 2 (Risk removal):** If we pair free troubleshooting with short‑term risk‑removal incentives (e.g., service credits or an extended renewal window) for recent drop‑off customers affected by the upgrade, it will rebuild trust after the disruption and reduce renewal friction.

- **Hypothesis 3 (Sequencing):** If we focus first on restoring usage and operational stability for recent drop‑off customers before explicitly discussing renewal, it will lead to higher renewal conversion than leading with renewal messaging while the product is still not working for them.

Would you like to validate these hypotheses next by defining success metrics or turning one of them into a concrete outreach experiment? [AI synthesized]

Would you like to iterate on the above strategy? Feel free to modify them.

Congratulations for going through a strategy formulation session! I will summarize below what we have discussed so far and crystallize the key outcomes into a clear, actionable recap.

As you move ahead to act on the strategy hypotheses, your unique strengths would help you…

• Bring calm, credibility, and trust into the CS‑led outreach by approaching restaurants in a composed, low‑pressure, service‑first manner. Your steady and non‑reactive style is well suited to positioning the “post‑upgrade health check” as genuine help, which supports restoring usage before naturally transitioning into renewal conversations.

• Execute the playbook efficiently by focusing on practical, concrete actions rather than over‑engineering the plan. By leaning into straightforward troubleshooting, clear value framing, and simple goodwill gestures, you can move quickly from issue resolution to renewal outcomes without unnecessary complexity, keeping momentum high across all three hypotheses. [AI synthesized]