High-Impact Discovery Questions for Selling to Revenue Enablement Leaders in Agencies

Summary:

Revenue Enablement Leads in agencies sit at the intersection of sales, client success, and operations. Their challenge is making sure go-to-market teams run efficiently, client pitches are consistent, and revenue processes scale without chaos. They’re measured on enablement ROI. Are teams ramping faster, closing smarter, and retaining clients?

‍

Effective discovery with this persona means uncovering gaps in their enablement playbooks, alignment struggles across departments, and metrics that prove revenue impact. Use these 30 questions to guide the conversation and show how a RevOps / GTM platform can unify strategy, data, and execution.

Early Discovery (Understand context + hook interest)

How do you currently enable your sales and client-facing teams across accounts?
What’s your biggest challenge in standardizing client pitches or proposals?
How do you share best practices across sales and account teams today
What tools are currently in place for training, onboarding, and coaching?
Where do you see gaps between your enablement initiatives and actual revenue impact?
How are new hires ramping, do you track time-to-productivity?
What feedback do you get from client-facing teams about current enablement resources?
How do you ensure consistency in messaging across different service lines?
Do you have visibility into which enablement content is being used (and working)?
How do you measure the effectiveness of enablement programs?

Qualification (Uncover priorities, buying signals)

What metrics are most important for evaluating revenue enablement success?
How closely do you work with RevOps, sales leadership, and delivery teams?
What systems are currently siloed—CRM, LMS, proposal tools, analytics?
Who’s responsible for final approval on enablement-related investments?
What’s your current budget allocation for enablement platforms or tools?
How do you prioritize between sales enablement and client success enablement?
Are there specific client segments where enablement challenges show up more?
How much of your team’s time is spent on manual reporting or tracking outcomes?
What internal objections do you face when rolling out new enablement processes?
What risks do you see in not modernizing your revenue enablement stack?

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

How often do deals stall because of misaligned messaging or proposals?
What’s the impact of inconsistent client presentations on win rates?
How do you track the correlation between enablement programs and revenue outcomes?
What would reducing ramp time for new hires by 20–30% mean for your bottom line?
How often do teams waste time searching for the right collateral or templates?
How do you measure adoption of new GTM strategies across sales teams?
What’s the cost of client churn tied to poor onboarding or inconsistent delivery?
How would automated insights on enablement effectiveness change your strategy?
What’s the downstream impact of not having a single source of truth for GTM assets?
How would better alignment between sales, RevOps, and client success impact agency growth?

How Pepsales AI Makes Discovery Smarter

Selling to enablement leaders isn’t about pitching features, it’s about showing how you’ll help them prove measurable impact. Pepsales AI equips your team with:

Persona-based discovery playbooks for enablement leaders in agencies
Real-time talk tracks and objection handling during calls
Automated CRM updates capturing key enablement KPIs and outcomes
MEDDPICC & BANT scoring to qualify deals more accurately
Analytics dashboards giving RevOps full visibility into enablement pipeline health

With Pepsales AI, your reps walk into every discovery call with smart, context-rich questions and leave with structured insights that move deals forward.

‍

‍Want to Power Smarter Discovery in Your GTM Motion?

‍Give your reps the playbooks and real-time intelligence they need to win more agency deals.Get Early Access to the Pepsales AI Copilot