Hello, Huan, thanks for connecting! I am DataDog, your AI coach 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 help you develop 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 — **Light / Partial Use** is a strong segment to focus on.

This group isn’t disengaged; they’re **under‑activated**. There’s still usage signal and an existing foothold, which means intent hasn’t disappeared. The core principle here is that this is **an activation and expansion challenge, not a revival**.

Compared to recent drop‑offs, it’s slightly harder because the issue is often **shallow adoption rather than a broken workflow**. That means success depends on **creating new habits and reinforcing value**, not just restoring something that already existed. Still, the probability of re‑engagement is high because you’re building on what’s already working rather than starting from zero. [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 customers or could recall the situations that might have triggered their behavior change? For example, did they stop engaging after a price change, a feature release, or a season?

That’s helpful — even when patterns aren’t obvious at first glance, the timing tells us something.

Looking closer at the **Light / Partial Use** group, there *is* a subtle pattern emerging: their reduced usage appears to correlate with **cost‑reduction behavior ahead of renewal**, rather than a loss of perceived value. In other words, they may still find APM useful but are deliberately using it less due to **pricing sensitivity**.

Notably, most of this usage reduction seems to cluster around **August / September**, which suggests a coordinated or external trigger rather than random disengagement.

Does that timeframe ring a bell for you? For example, do you recall any **pricing changes, contract adjustments, budget cycles, or internal cost‑control initiatives** on either our side or the customer side that typically happen around August or September? [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?

That makes sense — pricing is the core lever here and it’s something you can actively influence.

Now let’s make this actionable: **what strategic levers do you think you could use to address the pricing concern while still protecting renewal?**

For example, are you considering things like:

- Temporary incentives (e.g., renewal discounts, credits, or phased pricing)

- Reframing the value of the new feature vs. core features they already rely on

- Usage‑based adjustments or right‑sizing to align cost with actual usage

- Bundling or packaging changes to reduce perceived price shock

- Education on ROI or cost savings enabled by the new feature

Which of these feel realistic for your team, or are there other levers you’d want to explore? [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 totally fine — what you’ve outlined is already a strong foundation. You’ve clearly identified the core issue and the levers you can influence. Building on that, here are three clear, testable strategic hypotheses tailored to the **Light / Partial Use** segment and the pricing‑driven drop in usage:

- **If we proactively communicate that customers’ pricing remains unchanged unless they enable the new feature**, then light/partial‑use customers will feel less price anxiety and be more willing to maintain current usage levels and renew their existing license.

- **If we reframe the new feature as optional and flexible, paired with clear ROI messaging that shows when and why to enable it**, then customers will perceive greater control over cost and value, increasing renewal confidence even if they choose not to adopt the feature immediately.

- **If we combine transparent pricing education with targeted renewal incentives (e.g., limited‑time credits or phased adoption offers)** for light/partial‑use customers, then we can reduce renewal friction caused by the recent price increase and improve renewal rates without undermining long‑term pricing strategy.

If you’d like, we can now pick one of these and define success metrics, messaging, and a simple rollout plan to test it with a subset of customers. [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:

- **Customer segment to tackle**

- **Light / Partial Use customers** — still showing some activity but not fully adopting the solution. This is an activation and confidence‑building opportunity rather than a true re‑engagement or revival case.

- **Clear goal**

- **Renew their existing license** by reducing renewal friction and addressing cost concerns without eroding long‑term pricing strategy.

- **Diagnosis: why inactivity exists**

- The primary driver of reduced usage is a **pricing increase tied to a new feature** introduced around August–September.

- Customers did not lose perceived value in the core product; instead, they **reduced usage as a cost‑control response**, driven by price anxiety and uncertainty about how pricing works.

- **Prioritized strategic hypotheses (with key talking points)**

1. **Transparent pricing reassurance**

- *Hypothesis:* If we proactively communicate that pricing **does not change unless the new feature is enabled**, customers will feel less price anxiety and be more confident renewing.

- *Key talking points:*

- “Your current pricing stays the same if you don’t enable the new feature.”

- “You remain in full control of when and whether you adopt it.”

2. **Optional feature + ROI reframing**

- *Hypothesis:* If we clearly position the new feature as **optional and flexible**, supported by simple ROI framing, customers will better understand when it makes sense to adopt without feeling forced.

- *Key talking points:*

- “Adopt only when there’s a clear use case.”

- “Here’s how the feature pays for itself when you need it.”

3. **Targeted renewal incentives**

- *Hypothesis:* If we pair pricing education with **selective renewal incentives** (e.g., credits, phased adoption, or limited‑time offers), we can reduce renewal friction caused by the price increase and improve renewal rates.

- *Key talking points:*

- “We recognize the recent change and want to make renewal easy.”

- “Here’s a low‑risk way to renew while keeping future flexibility.”

You now have a clear segment focus, a well‑defined goal, a controllable root cause, and three testable strategies to move into execution with confidence. [AI synthesized]

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

- **Execute with discipline and consistency:** Leverage your conscientious approach to create clear, repeatable renewal playbooks (pricing explanation, ROI framing, incentive guidelines) and ensure every customer touchpoint delivers the same precise, confidence‑building message.

- **Lead calm, trust‑building customer conversations:** Use your emotional steadiness to handle pricing discussions with clarity and composure, reinforcing customer confidence by patiently explaining optionality, control, and long‑term value without pressure. [AI synthesized]