High-Impact Discovery Questions for Selling to Infrastructure Leaders in SaaS

Summary:

Surface scalability gaps, deployment bottlenecks, and compliance risks with tailored questions designed for complex SaaS and tech sales cycles.

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Infrastructure Heads at SaaS companies face unique challenges: scaling cloud environments, ensuring uptime for global users, balancing cost efficiency with performance, and keeping compliance intact across fast-moving teams. Effective discovery helps you align with what matters: reducing downtime, accelerating deployments, and enabling teams to innovate without sacrificing reliability. Use these 30 questions to drive productive discovery that resonates with SaaS 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 automation, CI/CD efficiency, observability, and infrastructure compliance.

Early Discovery (Understand context + hook interest)

What are your top infrastructure priorities this quarter, scalability, security, or cost optimization?
How do you currently monitor and manage uptime across your SaaS environments?
Where do you see the biggest delays in your software delivery pipeline?
How do you balance developer speed with infrastructure stability?
What’s your current process for handling production outages or incidents?
How do you manage compliance requirements (SOC 2, GDPR, HIPAA) within your DevOps workflows?
What challenges do you face with multi-cloud or hybrid infrastructure setups?
How do you ensure visibility across distributed systems and microservices?
What role do automation and self-service play in your current infrastructure strategy?
How do you onboard new developers or engineers into your CI/CD processes?

Qualification (Uncover priorities, buying signals)

What outcomes would justify adopting a new DevOps or infrastructure tool?
How do you measure ROI for DevOps initiatives, downtime reduction, deployment speed, or cloud cost savings?
Which KPIs are most important to your role, MTTR, deployment frequency, or system availability?
Who is typically involved in purchasing DevOps platforms, Engineering, Security, Finance?
What budget considerations or renewal cycles impact infrastructure investments?
Are you currently evaluating other platforms for monitoring, deployment, or compliance automation?
How well do your current DevOps tools integrate with your CI/CD pipelines and cloud providers?
What challenges do you face in scaling infrastructure without ballooning costs?
Are there regulatory or customer-driven pressures that influence your tool selection?
What risks do you see in maintaining your current infrastructure approach?

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

How much time is spent firefighting incidents versus building proactive improvements?
What’s the impact of delayed releases on customer satisfaction or churn?
How often do deployments fail or require rollbacks, and what’s the business cost?
What’s the downstream effect of poor observability on revenue or support costs?
How do you track and reduce mean time to resolution (MTTR) for critical incidents?
What’s the opportunity cost of engineers spending time on manual infra tasks instead of product innovation?
How would predictive insights into outages or bottlenecks change your operations?
How much effort goes into preparing for audits and compliance checks today?
How do you evaluate whether infrastructure changes are driving measurable outcomes?
If you could automate one part of your infrastructure lifecycle, what would it be, provisioning, monitoring, or compliance?

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 selling DevOps tools to a SaaS Infrastructure Head or enabling your team to run sharper technical discovery, Pepsales AI helps every conversation start strong and go deeper, faster.

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Want to Drive More Impactful Discovery?

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