Discovery Power Questions for Heads of Digital Marketing in Retail
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Summary:
Winning over retail marketing leaders requires you to understand how they drive footfall, boost online conversions, and unify customer experiences across channels.
The Head of Digital Marketing is under pressure to deliver measurable ROI from campaigns while managing fragmented tech stacks and changing shopper behavior. The right questions open doors to strategic conversations.
Here’s a curated set of 30 discovery questions, grouped by their mission-critical focus areas to help you position Martech/GTM SaaS solutions effectively.
Customer Acquisition & Engagement
- How are you balancing in-store traffic and digital engagement today?
- Which acquisition channels are driving the most profitable customers?
- How do you identify and target high-value customer segments?
- What’s your current approach to retargeting lapsed shoppers?
- Are you satisfied with the performance of paid media campaigns across platforms?
- What’s your strategy for engaging customers post-purchase to drive loyalty?
Marketing Performance & ROI
- How do you measure marketing effectiveness across online and offline channels?
- What’s the biggest challenge you face with campaign attribution?
- How confident are you in connecting marketing spend to store revenue?
- Which KPIs are you under the most pressure to improve this quarter?
- How do you ensure marketing initiatives align with merchandising and store operations?
- What’s your strategy for responding to underperforming campaigns in real time?
Omnichannel Integration
- How connected are your online and in-store customer journeys?
- What tools are you using to deliver a consistent omnichannel experience?
- Where do you see gaps in integrating eCommerce, app, and physical stores?
- How do you handle customer data across multiple platforms and touchpoints?
- What’s the impact of data silos on campaign performance?
- If you could unify one aspect of your digital and in-store strategy, what would it be?
Tech Stack Optimization
- How satisfied are you with your current MarTech stack?
- Are there any tools in your stack you’re considering replacing this year?
- How well do your marketing tools integrate with your CRM and POS systems?
- What’s the most time-consuming part of your team’s digital marketing workflow?
- How are you leveraging AI or automation in campaign management today?
- Where do you see the biggest opportunities to streamline marketing operations?
Innovation & Future Readiness
- What new marketing capabilities do you wish you had today?
- How do you experiment with emerging platforms like TikTok or retail media networks?
- What’s stopping you from launching more personalized or dynamic campaigns?
- How prepared is your team for upcoming seasonal peaks or market shifts?
- What trends in shopper behavior are most concerning for your strategy?
- If budget wasn’t a constraint, what’s the first area of marketing you’d transform?
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- Navigate complex omnichannel strategies with confidence
- Tie your solution directly to revenue and customer experience outcomes
- Guide conversations that position you as a strategic partner, not just another vendor
Pepsales helps you unlock higher-quality conversations that drive action.
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Equip your team with intelligent discovery prompts that uncover what really matters to digital marketing leaders in retail.
