Discovery Questions for Travel Tech Selling to Heads of Digital Strategy in Hospitality Chains
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Summary:
When speaking with Digital Strategy Heads at large or mid-size hospitality chains, it's essential to uncover how they're navigating the evolving digital landscape. These professionals are typically focused on digitizing the guest experience, increasing direct bookings, leveraging data for better decisions, and staying agile in a competitive hospitality market. To effectively position your Travel Tech solution, you’ll need to deeply understand their goals, current infrastructure, digital friction points, and vision for the guest journey.
30 Discovery Questions: Travel Tech × Digital Strategy Head × Hospitality Chains
A. Context & Priorities
- What are your top digital transformation goals for the next 12 months in the hospitality business?
- How has the shift in traveler behavior (post-COVID, AI, etc.) influenced your digital roadmap?
- What role does your digital strategy play in improving direct bookings vs. OTA reliance?
- Are there specific KPIs you're looking to impact—like conversion rate, loyalty, or average revenue per guest?
- What percentage of your bookings are currently influenced by digital touchpoints?
B. Current Tech Stack & Gaps
- What platforms are you using today to manage the end-to-end guest journey digitally?
- How integrated is your booking engine with CRM, loyalty programs, and channel managers?
- Are you currently using personalization on your website or booking portals?
- Do you feel your current tech stack supports dynamic pricing and inventory optimization effectively?
- Are you leveraging guest behavior data to create segmented offers or upsell campaigns?
C. Challenges & Frustrations
- Where do you see the most friction in the guest booking or check-in journey today?
- What digital experience gaps are hurting direct booking conversions?
- Are you struggling with data silos between marketing, ops, and guest services teams?
- How are your digital tools handling mobile-first users or last-minute bookings?
- Is it difficult to align digital experiences across multiple properties or locations?
D. Future Goals & Vision
- What would a fully connected and guest-personalized journey look like to you?
- Are you exploring AI-powered tools like recommendation engines or dynamic pricing?
- What technologies (AR/VR, smart rooms, AI chatbots) are you excited to test in the next year?
- How are you planning to leverage guest feedback and reviews more proactively?
- What role do you envision for automation in check-ins, upselling, or loyalty interactions?
E. Value, ROI, and Opportunity
- What kind of ROI do you expect from any new travel tech platform you implement?
- If you increased direct bookings by 10–15%, what would that mean for your P&L?
- How are you currently measuring digital ROI across the funnel (impressions to repeat bookings)?
- How does reducing dependency on OTAs fit into your digital profit strategy?
- What is the current cost of inefficiencies in your digital guest journey?
F. Stakeholders & Decision Process
- Who else in your organization is involved in evaluating or approving new digital initiatives?
- How closely do you work with your revenue, marketing, and IT heads when evaluating tech platforms?
G. Timelines & Budget
- Are you currently evaluating solutions, or is this part of a long-term transformation plan?
- Is there a fixed budget allocated for digital experience transformation this year?
H. Competitive Insight
- Are there any digital strategies or tech rollouts from competitors that caught your attention recently?
Why Pepsales AI is a Game-Changer Here
Pepsales AI gives Travel Tech teams an unfair advantage by:
- Surfacing CX, revenue, and digital readiness gaps early in the call
- Equipping reps with real-time questions aligned to the buyer’s strategy
- Auto-summarizing digital blockers and competitive insights
- Enabling value mapping tied directly to revenue & guest satisfaction
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