High-Impact Discovery Questions for Selling to Heads of Sales Enablement in Tech / SaaS

Summary:

Uncover enablement gaps, optimize GTM execution, and accelerate revenue alignment with questions tailored for Heads of Sales Enablement in SaaS.

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If you’re selling a GTM tool (like Pepsales AI) to Heads of Sales Enablement in Tech/SaaS, discovery is critical. These leaders are tasked with equipping reps, scaling onboarding, driving adoption of GTM strategies, and ensuring cross-functional alignment between marketing, sales, and product. The right questions help you uncover how enablement leaders currently support GTM motions and where smarter tools can make the difference.

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Below is a curated set of 30 discovery questions designed for SaaS Heads of Sales Enablement, spanning early discovery, qualification, and deep needs analysis. Perfect for positioning tools that strengthen onboarding, coaching, content alignment, and GTM effectiveness.

Early Discovery (Understand Context & Current Priorities)

What are your top sales enablement priorities for upcoming GTM initiatives?
How do you currently align enablement with product launches or market expansion?
What challenges do you face in scaling onboarding across fast-growing SaaS teams?
How do you ensure reps adopt new messaging and positioning effectively?
Where do you see the biggest gaps in readiness for GTM execution?
How are you measuring rep productivity and enablement ROI today?
How do managers track whether coaching is applied in live selling?
What tools or processes are you currently using to deliver enablement content?
How do reps access GTM resources during live customer conversations?
How do you balance enablement needs between new hires and tenured reps?

Qualification (Surface Buying Signals & Priorities)

What criteria do you use to evaluate new GTM or enablement tools?
Are you focused more on faster onboarding, better adoption of GTM strategy, or pipeline impact?
Which metrics are most important to you—time to quota, content usage, win rates, or rep productivity?
Who else is involved in enablement technology decisions (RevOps, Product Marketing, Sales Leaders)?
What’s your timeline for exploring or implementing new GTM tools?
Have you tried other enablement or GTM platforms in the past?
How important is integration with your CRM, LMS, or CMS?
Do you already have a budget earmarked for GTM execution or enablement this year?
What challenges do you face in driving adoption of new tools across sales teams?
Are there concerns internally about ROI proof, rep engagement, or cross-functional alignment?

Deep Needs Analysis (Quantify Pain & Tie to Outcomes)

How much time do managers spend manually preparing reps for GTM rollouts?
What’s the cost of longer ramp time during product launches?
How do you measure the impact of enablement on win rates?
What percentage of your GTM content is actively used in selling conversations?
How do you identify gaps in adoption of new messaging or sales plays?
What’s the biggest challenge in ensuring consistent GTM execution across global teams?
How much effort is spent prepping reps for competitive positioning in the field?
What would a 10–15% improvement in content adoption or ramp time mean for quarterly targets?
How do you connect enablement metrics back to revenue outcomes?
If you could automate one part of GTM enablement, what would it be?

How Pepsales AI Makes Discovery Smarter

Pepsales AI acts as a real-time GTM copilot, helping reps and enablement leaders uncover insights and stay aligned with strategy. With role-specific and SaaS-aware discovery prompts, every conversation ties back to GTM goals and revenue outcomes.

What You Get:

Persona-based question libraries for Heads of Sales Enablement in SaaS
Smart prompts that adjust to objections, sales stage, or role
Coaching insights that connect GTM execution to measurable revenue impact
Automated prep for discovery calls, product rollouts, and enablement sessions

For enablement leaders, this means less manual prep, higher adoption of GTM strategy, and faster execution at scale.

Want to Drive More Impactful Discovery?

Equip your teams with questions that accelerate adoption, shorten ramp time, and prove GTM ROI.

Get a free trial of the Pepsales AI Copilot