High-Impact Discovery Questions for Selling to Sales Enablement Leads in Tech / SaaS
.avif)
Summary:
Uncover enablement gaps, align with growth targets, and accelerate adoption with questions tailored for Sales Enablement leaders in SaaS.
If you’re selling SalesTech or Enablement solutions to Sales Enablement Leads in Tech/SaaS, discovery is critical. These leaders are measured on how well they scale onboarding, shorten ramp time, drive rep productivity, and align content/tools to revenue outcomes. The right discovery questions help you surface enablement challenges across fast-growing, often globally distributed teams.
Below is a curated set of 30 discovery questions designed for this persona, spanning early discovery, qualification, and deep needs analysis. Perfect for tools focused on rep onboarding, coaching, content alignment, and performance visibility.
Early Discovery (Understand Context & Current Processes)
- What are your top enablement priorities for this quarter?
- How are you measuring the effectiveness of your enablement programs today?
- Where do you see the biggest gaps in rep readiness or performance?
- How long does it typically take new hires to ramp to quota?
- How do you currently align enablement programs with product launches or GTM motions?
- What challenges do you face in scaling training across global teams?
- How do reps access sales content during live customer conversations?
- What tools or systems are you currently using to deliver enablement?
- How do you track the ROI of training and content usage?
- How often do managers get visibility into how reps are applying coaching?
Qualification (Surface Buying Signals & Priorities)
- What criteria do you use to evaluate new enablement technology?
- Are you focused more on faster onboarding, rep productivity, or coaching effectiveness right now?
- What key metrics would you want to improve with an enablement solution?
- Who else (sales ops, revenue leaders, product marketing) is involved in enablement decisions?
- What is your timeline for exploring new tools this year?
- Have you tried other enablement platforms or LMS tools before?
- How important is integration with your CRM, CMS, or collaboration tools?
- Do you already have budget allocated to enablement initiatives?
- What barriers currently prevent you from scaling enablement effectively?
- Are there concerns around adoption, rep engagement, or ROI proof points?
Deep Needs Analysis (Quantify Pain & Tie to Outcomes)
- How much time do managers spend on manual coaching or deal reviews?
- What’s the cost of longer ramp time on your revenue goals?
- How do you ensure reps adopt new messaging or positioning quickly?
- What percentage of your content is actually used in live selling?
- How do you measure whether enablement programs change rep behavior?
- What’s the biggest challenge in providing just-in-time coaching during deals?
- How do you identify skill gaps across teams without relying on anecdotal manager feedback?
- How much effort is spent prepping reps for new product rollouts?
- What would it mean if ramp time decreased by even 10–15%?
- If you could automate one part of coaching or training, what would it be?
How Pepsales AI Makes Discovery Smarter
Pepsales AI helps your sales team (and your enablement function) ask the right questions and capture the right insights in real time. With role-specific and industry-aware discovery prompts, reps stay aligned with enablement goals and customer needs.
What You Get:
- Persona-based question libraries for sales enablement leaders in SaaS
- Smart prompts that adapt to objections, sales stage, or role
- Coaching insights that connect enablement to revenue outcomes
- Faster prep for discovery calls, demos, and onboarding sessions
Enablement leaders can finally ensure reps not only learn but apply discovery best practices in live customer conversations.
Want to Drive More Impactful Discovery?
Equip your reps with questions that shorten ramp time, increase adoption, and prove enablement ROI.
