High-Impact Discovery Questions for Selling to the Head of Sales in Tech/SaaS

Summary:

Uncover real pain points, align on outcomes, and accelerate qualification with questions tailored for SaaS sales leaders.

‍

If you sell SalesTech or Enablement tools to Heads of Sales at tech/SaaS companies, discovery is where the deal is won or lost. The right questions help surface business pain, align on value, and drive urgency.

‍

Here’s a curated library of 30 discovery questions you can use across early discovery, qualification, and deep needs analysis. These questions are ideal for reps selling to senior sales leaders, especially when positioning tools that improve team performance, pipeline visibility, and sales process optimization.

Early Discovery (Understand context + hook interest)

What are your top sales priorities this quarter?
What triggered your interest in exploring new sales tools?
How are you currently tracking rep performance and productivity?
What’s the biggest challenge your team is facing when it comes to hitting quota?
How confident are you in your pipeline accuracy right now?
What’s the biggest bottleneck in your sales process today?
Are you planning any changes to your sales tech stack this year?
How do you currently prepare your team for discovery or closing calls?
What kind of sales enablement support do your reps use today?
How would you describe your current approach to deal coaching?

‍

Qualification (Uncover priorities, buying signals)

How do you evaluate new sales tools, what matters most to you?
What outcomes would justify investing in a new enablement platform?
What metrics would you need to see improve to consider this a success?
Who else is typically involved in the decision for a solution like this?
What’s your timeline for evaluating or adopting new tools?
Have you tried solving this challenge with other tools before?
Are you currently evaluating other solutions in this space?
Is the budget already allocated for solving this?
What’s stopping your team from fixing this today?
What other priorities are competing for attention right now?

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

How do you identify skill gaps or training needs on your team?
How often do reps miss quota due to poor qualification or missed signals?
What’s the impact of inaccurate forecasts on your leadership reporting?
How long does it take to ramp a new rep to full productivity?
How do you ensure your team is asking the right discovery questions on calls?
What’s the cost of stuck or lost deals due to poor discovery?
How much manual effort goes into preparing for calls today?
What would a 10% increase in win rate mean to your revenue this quarter?
How do you currently review sales calls for coaching purposes?
If you could automate one part of the sales discovery process, what would it be?

How Pepsales AI Helps

‍

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.

‍

What it delivers:

A library of proven questions per industry, persona, and product
Smart prompts that adapt to buyer role, objections, and stage
Embedded coaching and insights to guide better conversations
Automation of discovery prep, no more guesswork

Whether you’re prepping for a demo or coaching new reps, Pepsales AI ensures every conversation starts strong and gets to the real need, fast.

‍

Ready to unlock higher-quality discovery conversations?

‍

Get a free trial of the Pepsales AI Copilot
Equip your team with questions that uncover real problems, build urgency, and close more deals.