High-Impact Discovery Questions for Selling Cybersecurity Solutions to CTOs in Real Estate / PropTech
.avif)
Summary:
Uncover critical IT vulnerabilities, align with digital transformation goals, and fast-track decision-making with tailored discovery questions for CTOs in the real estate and PropTech sector.
CTOs in Real Estate are focused on enabling smart, connected properties, optimizing digital platforms, and securing data across tenants, systems, and partners. For Cybersecurity/IT vendors, the discovery stage is the key moment to identify gaps, align on tech vision, and create urgency.
30 Discovery Questions for CTOs in Real Estate / PropTech (Cybersecurity / IT Solutions)
A. Initial Qualification & Context Setting
- What are your top 2–3 technology and cybersecurity priorities over the next 12–18 months?
- What has triggered your interest in exploring new cybersecurity or IT solutions at this stage of your digital roadmap?
- How does your current cybersecurity strategy align with your organization’s smart building, tenant experience, or digital leasing initiatives?
- Are there recent incidents, audits, or compliance concerns influencing your current focus on security?
- Would you describe your current tech stack as more legacy, hybrid, or fully cloud-native?
B. Current State & Challenges (Pain Points)
- How are you currently securing IoT and smart building infrastructure across your real estate assets?
- What risks are you facing when integrating third-party platforms (e.g., CRMs, leasing platforms, energy management systems)?
- Are there challenges in managing access and identity across multiple stakeholders, tenants, contractors, agents?
- How confident are you in your current ability to prevent data breaches related to property transactions or tenant PII?
- What issues are your teams experiencing with network visibility across properties, especially for remote access or mobile workforce?
- How are you managing cybersecurity across mixed-use buildings or geographically dispersed properties?
- Are manual processes or disjointed tools creating delays in incident response or threat detection?
- What are your biggest headaches with maintaining uptime, connectivity, and security across your digital platforms?
- Do you face internal resistance or bandwidth issues when enforcing security best practices across IT and property operations teams?
- Are you concerned about the growing threat landscape around ransomware, smart device hijacking, or real estate fraud?
C. Desired Future State & Goals (Aspirations)
- If you could enhance one part of your IT security framework tomorrow, what would it be and why?
- What does a fully secured and digitally connected building portfolio look like for your team?
- How would enhanced automation, real-time analytics, or AI improve your cybersecurity and IT operations?
- In what ways are you aiming to improve tenant data protection and digital trust?
- What kind of business outcomes are you targeting, reduced security risk, improved asset performance, or competitive differentiation?
D. Impact & Value Quantification
- What is the cost to your organization of a potential breach or system downtime — reputationally, financially, and legally?
- How much time is your IT team spending on manual security tasks that could be automated?
- What are the regulatory implications or insurance risks associated with your current security posture?
- How does inefficient access control or network segmentation affect tenant experience or operational costs?
- What would a 30–50% reduction in IT incidents or alerts mean for your internal capacity and business continuity?
E. Decision-Making Process & Stakeholders
- Who else in your leadership or operations teams would be involved in evaluating a cybersecurity solution, property managers, COO, legal, etc.?
- What are the most critical evaluation criteria when choosing a technology partner in your space?
F. Budget & Resources
- Do you have a dedicated cybersecurity or PropTech innovation budget this year, or is this investment still in the planning phase?
G. Timeline & Urgency
- Are there any large-scale projects, compliance timelines, or infrastructure upgrades influencing your buying window?
H. Competition & Alternatives
- Have you evaluated other cybersecurity or IT vendors recently? What were the gaps you noticed in those solutions?
How Pepsales AI Helps
Pepsales AI helps sales teams ask the right questions, faster. It delivers intelligent, role-specific, and industry-aware discovery questions in real time tailored to the context of each deal.
Key Features:
- A curated database of proven discovery questions by buyer role and vertical
- Real-time deal-aware coaching prompts to overcome objections or deepen insight
- Discovery prep automation, remove the guesswork and focus on value
- Built-in tools for question mapping, note-taking, and post-call summaries
Whether your reps are engaging in a smart city discussion or solving IoT security gaps, Pepsales AI ensures they ask the right questions to get to the real opportunity faster.
Ready to Win More Deals in Real Estate Tech?
