High-Impact Discovery Questions for Selling to Data Leaders in Retail

Summary:

Expose data silos, align with customer intelligence needs, and uncover real ROI drivers with questions tailored for insights leaders in retail.
Retail decision-makers are flooded with fragmented data. If you sell AI/Analytics solutions to Data or Insights Leads, you need discovery questions that surface gaps in visibility, personalization, and operations.

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Here’s a ready-to-use set of 30 questions mapped to retail buying cycles, perfect for driving urgency and showing the strategic value of your platform.

Early Discovery (Understand context + hook interest)

What are your biggest data priorities this retail cycle, forecasting, personalization, or CX?
How are you tracking shopper behavior across online and offline touchpoints?
What’s the biggest challenge in unifying or accessing customer data?
How do you currently analyze merchandising or promotional performance?
What tools or dashboards are you using for real-time store or eComm insights?
Are marketing and merchandising teams working from the same data sets?
Where do you face delays in generating or delivering insights to other teams?
What’s your biggest bottleneck in launching new analytics initiatives?
Are you using predictive models for demand planning or pricing today?
How do you monitor and act on returns, cart abandonment, or churn signals?

Qualification (Uncover priorities, buying signals)

What would success look like from an AI or analytics investment this year?
What are the most important KPIs your execs care about right now?
Are you trying to centralize data or make it more self-service for business users?
Who typically champions or sponsors analytics initiatives internally?
Have you tried solving this with internal BI teams or off-the-shelf dashboards?
Are there silos between ecommerce, stores, and supply chain data?
How important is real-time or near-real-time access to insights?
What would help your team move faster—cleaner data, better modeling, or automation?
Is this tied to a broader transformation (CDP rollout, CX overhaul, etc.)?
What’s the biggest blocker to scaling analytics across teams today?

Deep Needs Analysis (Tie value to goals, quantify pain)

What’s the impact of slow insight delivery on campaign or inventory performance?
How much manual effort goes into preparing reports across channels?
What would a 10% improvement in personalized targeting mean to your revenue?
How much time is lost when teams operate from different data sets?
What’s the cost of poor visibility into product performance or shopper intent?
How do you measure ROI on existing analytics tools or platforms?
What gaps exist in your understanding of customer journey or CLV?
How confident are you in your current data quality or accuracy?
What reporting or insight do senior leaders keep asking for that’s hard to deliver?
If you could automate one retail analytics workflow tomorrow, what would it be?

How Pepsales AI Helps

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Pepsales AI helps sales teams ask the right questions, faster. It delivers intelligent, role-specific, and industry-aware discovery questions in real time tailored to the context of each deal.

What it delivers:

A library of proven questions per industry, persona, and product
Smart prompts that adapt to buyer role, objections, and stage
Embedded coaching and insights to guide better conversations
Automation of discovery prep, no more guesswork

Whether you’re prepping for a demo or coaching new reps, Pepsales AI ensures every conversation starts strong and gets to the real need, fast.

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Ready to unlock higher-quality discovery conversations?

Get Early Access to the Pepsales AI Discovery Copilot
Equip your team with questions that uncover real problems, build urgency, and close more deals.