High-Impact Discovery Questions for Selling to Heads of Operations in Logistics

Summary:

Heads of Operations in logistics live under constant pressure, tight delivery windows, razor-thin margins, fluctuating fuel and labor costs, and client expectations for speed and visibility. Their focus is keeping the supply chain moving while improving efficiency and cutting waste.

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When selling Productivity / Ops SaaS into this role, the key is showing how technology can simplify workflows, reduce bottlenecks, and provide real-time insights into fleet, warehouse, and delivery performance. These 30 discovery questions help you uncover operational inefficiencies, automation opportunities, and the ROI they expect from digital transformation.

Early Discovery (Understand context + hook interest)

What are your top 3 operational priorities for the next quarter?
How do you currently track and manage daily logistics operations?
What systems or tools are in place for fleet and warehouse coordination?
Where do you see the most recurring delays or bottlenecks?
How do you balance cost efficiency with on-time delivery goals?
What KPIs are most critical for your operations dashboard today?
How do you track real-time exceptions like delays or reroutes?
What’s your biggest challenge in workforce scheduling and resource allocation?
How do you currently communicate changes to drivers, warehouses, and clients?
Where do manual processes still slow you down?

Qualification (Uncover priorities, buying signals)

How do you measure operational efficiency across your logistics network?
What level of visibility do you currently have into the end-to-end supply chain?
Which tools do you integrate today—ERP, TMS, WMS, or others?
How do you prioritize investments between fleet, warehouse, and technology upgrades?
What part of operations eats up the most time and resources today?
Do you face challenges with siloed data between teams or systems?
How often do service-level agreements (SLAs) get impacted by inefficiencies?
What is the process for investigating and resolving missed deliveries?
Who is typically involved in approving new operations platforms?
What’s your budget outlook for operations digitization in the next 12 months?

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

How much time does your team spend on manual reporting each week?
What’s the cost impact of recurring delivery errors or misrouted shipments?
How does limited visibility into operations affect customer satisfaction?
What savings would come from reducing fuel waste or idle time by 10–15%?
How often do teams have to work overtime to meet delivery targets?
What’s the impact of not having real-time alerts when shipments are delayed?
How do you measure the ROI of process improvements in your operations?
How would centralizing communication and task management improve efficiency?
What would it mean if you could predict and prevent delays before they occur?
How much competitive advantage would streamlined, automated ops give your logistics network?

How Pepsales AI Makes Discovery Smarter

For complex roles like the Head of Operations, discovery isn’t about features, it’s about uncovering inefficiencies and quantifying impact. Pepsales AI equips your team with:

Persona-based discovery playbooks tailored for logistics operations leaders
Real-time talk tracks & objection handling focused on efficiency, cost, and visibility
Automated CRM capture of operational KPIs, pain points, and decision criteria
Deal qualification frameworks (MEDDPICC, BANT) that ensure reps focus on real opportunities
Pipeline intelligence giving RevOps and sales leaders full visibility into logistics deals

With Pepsales AI, your sales team goes beyond surface-level questions and uncovers the operational value drivers that make your Productivity / Ops SaaS indispensable.

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