High-Impact Discovery Questions for Selling to Digital Strategy Leaders in Travel

Summary:

Surface digital gaps, booking inefficiencies, and revenue growth opportunities with tailored questions designed for modern travel agency sales cycles.

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Digital Strategy Heads at travel agencies face mounting pressures: customer expectations for seamless digital experiences, rising competition from OTAs, and the need to integrate fragmented booking, payment, and loyalty systems. Effective discovery helps you align with what matters: reducing manual processes, improving personalization, and unlocking new revenue streams. Use these 30 questions to drive productive discovery that resonates with travel buyers.

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Here’s a curated set of 30 discovery questions spanning early discovery, qualification, and deep needs analysis, perfect for tools focused on booking automation, omnichannel personalization, and digital transformation.

Early Discovery (Understand context + hook interest)

What’s your top digital priority this year, improving online bookings, loyalty, or personalization?
How do you currently track and optimize customer booking journeys?
Where are you seeing the biggest drop-offs in your digital funnel?
What challenges do agents face when managing online and offline bookings together?
How consistent is customer experience across mobile, desktop, and in-person channels?
Are you looking to reduce manual effort in payment processing, refunds, or itinerary management?
What’s your biggest concern with digital competition from OTAs or direct airline/hotel bookings?
How do you currently onboard new digital tools across sales and service teams?
What platforms are you using today for CRM, booking management, or personalization?
How do you prepare for peak travel seasons digitally—holiday rushes, festival travel, or corporate spikes?

Qualification (Uncover priorities, buying signals)

What outcomes would justify investing in a new travel tech or digital transformation tool?
How do you evaluate ROI for digital initiatives, conversion lift, revenue per booking, or customer retention?
Which KPIs matter most for your strategy, average booking value, repeat customer rate, or booking speed?
Who signs off on digital platform investments, IT, Finance, or Strategy?
What’s your typical timeline for rolling out new digital tools?
Are you currently comparing platforms for automation, loyalty, or omnichannel experience?
How well do your current tools integrate with GDS, CRM, or marketing automation systems?
What budget considerations or seasonal cycles affect digital investments?
What internal challenges slow down adoption of new digital platforms?
Are there risks in sticking with legacy systems that you’re actively trying to mitigate?

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

What’s your average time-to-market for launching new digital campaigns or offers?
How do booking errors or system downtime impact customer satisfaction and revenue?
What’s the downstream impact of poor digital onboarding on customer retention?
How do you detect and fix inconsistencies in pricing, itineraries, or promotions?
How often do you review digital agent-customer interactions for optimization?
How much time is spent manually managing itineraries, rebookings, or cancellations?
What would more personalization across booking journeys mean for revenue and loyalty?
What’s the opportunity cost of not capturing upsell or cross-sell opportunities digitally?
How would a 10% increase in booking conversion impact your quarterly numbers?
If you could automate one part of your digital travel workflow, what would it be search, booking, or post-travel engagement?

How Pepsales AI Makes Discovery Smarter

Pepsales AI empowers your sales team to ask the right questions, faster and more effectively. It delivers intelligent, role-specific, and industry-aware discovery questions in real time tailored to the context of each deal.

What You Get:

A ready-to-use library of proven questions by persona, industry, and product
Smart, dynamic prompts that adapt to objections, buyer roles, and sales stages
Built-in coaching to help reps lead more impactful conversations
Automated prep, no more guesswork before discovery calls

Whether you’re pitching a digital transformation platform to a Travel Strategy Head or preparing agents for omnichannel selling, Pepsales AI helps every conversation start strong and go deeper, faster.

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Want to Drive More Impactful Discovery?

‍Arm your team with questions that uncover pain, build urgency, and move deals forward. Get Early Access to the Pepsales AI Discovery Copilot