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High-Impact Discovery Questions for Selling to Digital Marketing Leaders in E-commerce

Summary:

Surface growth gaps, campaign inefficiencies, and ROI opportunities with tailored questions designed for fast-paced e-commerce and D2C sales cycles.

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Digital marketing leaders in e-commerce face increasing pressure to drive conversions, optimize campaigns, and prove ROI across multiple channels. Effective discovery helps you align with what matters: improving marketing automation, enhancing customer engagement, scaling campaigns, and maximizing digital spend efficiency. Use these 30 questions to drive productive discovery that resonates with digital marketing 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 campaign optimization.

Early Discovery (Understand context + hook interest)

  1. What are your top marketing priorities this quarter customer acquisition, retention, or conversion optimization?
  2. How do you currently track campaign performance across channels?
  3. What challenges do your marketing teams face in scaling campaigns effectively?
  4. How do you manage cross-channel messaging consistency?
  5. Which MarTech tools or platforms are currently in use?
  6. How much time is spent manually analyzing performance or creating reports?
  7. What internal processes slow down campaign execution or optimization?
  8. How do you onboard new marketing team members across digital channels?
  9. How do you ensure compliance with data privacy regulations like GDPR or CCPA?
  10. How do you prepare for high-stakes campaigns, seasonal launches, or product rollouts?

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Qualification (Uncover priorities, buying signals)

  1. What outcomes would justify adopting a new marketing automation or GTM platform?
  2. How do you evaluate ROI for MarTech tools in your e-commerce business?
  3. Are there specific KPIs (CAC, LTV, ROAS, conversion rates) that matter most?
  4. Who approves MarTech investments Marketing, IT, or Finance?
  5. What’s your expected rollout timeline for new tools or processes?
  6. Are you exploring other platforms for campaign automation or analytics?
  7. How well do your current tools integrate with your e-commerce and CRM systems?
  8. What budget cycles or constraints impact MarTech adoption?
  9. What internal blockers prevent faster adoption of new marketing tools?
  10. Are there risks with maintaining the current marketing tech stack 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 campaign processes affect ROI and customer engagement?
  4. How do you currently 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 digital marketing initiatives on overall revenue growth?
  8. Are there missed opportunities where better automation could improve results?
  9. If you could automate one major part of your campaign execution or analysis, what would it be?
  10. How would real-time campaign insights change your decision-making and budget allocation?

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How Pepsales AI Makes Discovery Smarter

Pepsales AI empowers digital marketing 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 marketing 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 marketing leaders lead more impactful conversations
  • Automated prep no more guesswork before discovery calls

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

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‍Want to Drive More Impactful Discovery?

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