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

Summary:

Surface growth gaps, campaign inefficiencies, and ROI opportunities with tailored questions designed for dynamic retail environments.

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Retail growth leaders face pressures to increase customer acquisition, retention, and omnichannel sales while managing marketing spend effectively. Effective discovery helps you align with what matters: scaling campaigns, optimizing GTM strategies, improving automation, and maximizing revenue growth. Use these 30 questions to drive productive discovery that resonates with retail growth leaders.

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Here’s a curated set of 30 discovery questions spanning early discovery, qualification, and deep needs analysis, perfect for tools focused on marketing automation, GTM enablement, and growth analytics.

Early Discovery (Understand context + hook interest)

  1. What are your top growth priorities this quarter customer acquisition, retention, or omnichannel expansion?
  2. How do you currently track performance across online and offline retail channels?
  3. What challenges do your growth teams face in scaling campaigns effectively?
  4. How do you ensure consistent messaging across channels and touchpoints?
  5. Which MarTech or GTM tools are currently in use?
  6. How much time does your team spend manually analyzing campaign performance?
  7. What internal processes slow down GTM execution or optimization?
  8. How do you onboard new growth team members across different retail channels?
  9. How do you ensure compliance with data privacy regulations like GDPR or CCPA?
  10. How do you prepare for high-stakes seasonal campaigns or product launches?

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Qualification (Uncover priorities, buying signals)

  1. What outcomes would justify adopting a new growth or marketing automation platform?
  2. How do you evaluate ROI for MarTech tools in retail?
  3. Are there specific KPIs (CAC, LTV, conversion rates, sales growth) that matter most?
  4. Who approves investments in growth or marketing tools Growth, Marketing, or Finance?
  5. What’s your expected rollout timeline for new tools or GTM processes?
  6. Are you currently exploring other platforms for growth automation or analytics?
  7. How well do your current tools integrate with your e-commerce, CRM, or POS systems?
  8. What budget cycles or constraints affect GTM tool adoption?
  9. What internal blockers prevent faster adoption of new growth tools?
  10. Are there risks with maintaining the current processes that you’re trying to mitigate?

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

  1. How much time does your team spend manually creating reports or dashboards?
  2. What is the financial impact of underperforming campaigns or low conversion rates?
  3. How do inefficient GTM processes affect ROI and customer acquisition?
  4. How do you track campaign effectiveness across paid, owned, and earned channels?
  5. How much effort is required to optimize campaigns and adjust budgets in real time?
  6. What would improved cross-channel visibility mean for customer acquisition and retention?
  7. How do you measure the impact of growth initiatives on overall retail revenue?
  8. Are there missed opportunities where better automation could improve results?
  9. If you could automate one major part of your GTM or growth process, what would it be?
  10. How would real-time insights into campaign performance change your decision-making and budget allocation?

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How Pepsales AI Makes Discovery Smarter

Pepsales AI empowers retail growth leaders to ask the right questions, faster and more effectively. It delivers intelligent, role-specific, and industry-aware discovery prompts in real time tailored to each growth context.

What You Get:

  • A ready-to-use library of proven questions by persona, industry, and product
  • Smart prompts that adapt to objections, buyer roles, and campaign stages
  • Built-in coaching to help growth leaders lead more impactful conversations
  • Automated prep no more guesswork before discovery calls

Whether you're evaluating a new MarTech platform, scaling GTM campaigns, or optimizing growth strategies, Pepsales AI helps every conversation start strong and get to the real need, fast.

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