High-Impact Discovery Questions for Selling Martech to CMOs in E-commerce / D2C

Summary:

Uncover what really drives marketing leaders in E-commerce and D2C brands. These discovery questions are designed to surface strategic priorities, expose operational gaps, and align your Martech or GTM SaaS solution to the outcomes CMOs care about most.

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In fast-moving digital commerce, your buyers are juggling customer acquisition costs, retention strategies, and ROI pressures. The right questions help you cut through the noise, earn trust, and accelerate your deals.

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Here’s a curated library of 30 discovery questions grouped into 6 key categories to help your reps deliver value-driven conversations with marketing executives.

1. Business & Growth Priorities

What are your top 3 growth objectives for the next 12 months?
How are you balancing customer acquisition versus retention this year?
Which channels (paid, organic, social, marketplaces) are driving the most profitable growth?
Are you focused more on expanding in existing markets or entering new ones?
What role does your MarTech stack play in achieving these goals?

2. Marketing Strategy & Execution

How do you currently approach campaign orchestration across channels?
What’s the biggest bottleneck in executing your GTM campaigns today?
How do you personalize experiences across different customer segments?
What’s your current strategy for growing customer lifetime value (LTV)?
How do you measure success for key campaigns, what metrics matter most?

3. Data, Insights & Decision Making

How confident are you in your attribution models for marketing spend?
What tools are you using for real-time marketing analytics and reporting?
How do you identify and react to shifts in customer behavior?
What’s the impact of delayed insights on your team’s agility?
How do you currently manage and unify first-party and third-party data?

4. Tech Stack & Automation

Are you planning any changes to your MarTech stack this year?
How well do your current tools integrate with each other and your ecommerce platform?
What’s the most manual or time-consuming part of your marketing operations today?
Where do you see opportunities to automate repetitive tasks?
Have you tried solving these challenges with other platforms in the past?

5. Budget & Investment Readiness

Is budget already allocated for marketing technology improvements this quarter?
How do you evaluate ROI when considering new tools or platforms?
Who else in the organization is involved in decisions about Martech investments?
What’s your timeline for evaluating and implementing new solutions?
What other initiatives are competing for your budget or attention right now?

6. Risk, Challenges & Missed Opportunities

What’s the cost of a failed or underperforming campaign to your business?
How much revenue is lost due to poor customer retention?
What risks do you see in not modernizing your MarTech stack?
How often do you experience inefficiencies due to data silos or misaligned teams?
What’s keeping you up at night when it comes to marketing performance?

How Pepsales AI Supercharges Discovery

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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.

Dynamic Question Prompts
Reps get intelligent prompts tailored to the buyer persona, industry, and stage of the deal.
Embedded Coaching
Real-time coaching ensures even new reps run discovery calls like seasoned pros.
Discovery Automation
Stop wasting hours preparing for calls. Pepsales AI generates impactful discovery flows and insights in seconds.
Industry-Aware Playbooks
Access pre-built question libraries and objection-handling tips for e-commerce, SaaS, and more.

Ready to Equip Your Team for Better Discovery?

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Get a demo of Pepsales AI Discovery Copilot

Uncover deeper insights, align with CMO priorities, and close more deals with Pepsales AI.