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Discovery Questions That Resonate with CTOs & VPs of Engineering in SaaS & Tech Companies

Summary:

For CTOs and VPs of Engineering in high-growth SaaS companies, success depends on accelerating software delivery without compromising stability, security, or team efficiency. Your discovery questions should surface pain points around deployment bottlenecks, infrastructure scalability, developer productivity, and tool fragmentation while positioning your DevOps tool as the solution to streamline engineering velocity, automation, and resilience.

Here’s a set of 30 tailored discovery questions to guide high-impact conversations.

1. Deployment Velocity and Release Management

  1. What’s your biggest challenge in getting code from commit to production quickly and reliably?
  2. How often do deployment delays impact feature delivery or product roadmaps?
  3. Do you have a clearly defined release process or does it vary across teams?
  4. How confident are you in your rollback or hotfix capabilities when something goes wrong?
  5. If you could improve one aspect of your CI/CD pipeline today, what would it be?

2. Infrastructure, Scalability & Reliability

  1. How are you managing infrastructure provisioning across environments?
  2. What’s your current strategy for scaling infrastructure during peak load periods?
  3. Are infrastructure changes introducing instability into production systems?
  4. How often do outages or incidents relate to manual configurations or environment drift?
  5. Where do you see the biggest friction between development and operations teams?

3. Developer Experience and Workflow Efficiency

  1. Are your developers spending too much time on DevOps tasks that could be automated?
  2. What tools are currently in your DevOps stack, and where are the gaps?
  3. How easy is it for a developer to spin up a local or staging environment?
  4. Are long feedback loops slowing down engineering productivity?
  5. If you could remove one repetitive task from your engineering team's workflow, what would it be?

4. Observability, Monitoring & Incident Response

  1. Do you have real-time visibility into the health of your systems post-deployment?
  2. How do you currently detect and respond to production incidents?
  3. Are teams able to trace issues across services and environments quickly enough?
  4. Is there a unified view of logs, metrics, and traces or are they siloed?
  5. Where do you face challenges in root cause analysis or mean-time-to-resolution (MTTR)?

5. Security, Compliance, and Governance

  1. How are security and compliance integrated into your DevOps workflows?
  2. Are your teams equipped to handle secrets management, role access, and infrastructure as code audits?
  3. How often do you run into friction between compliance requirements and delivery speed?
  4. Do you have visibility into what’s being deployed, where, and by whom across all environments?
  5. What are your biggest concerns around infrastructure or pipeline security today?

6. Strategic Alignment and Future Scaling

  1. As you grow, how do you plan to scale your DevOps practices across more teams and services?
  2. Are you currently investing in platform engineering or internal developer platforms (IDPs)?
  3. What KPIs or metrics do you use to measure DevOps success across your org?
  4. How aligned are your engineering, security, and SRE teams on shared goals?
  5. If you could solve one DevOps pain point that’s slowing down innovation, what would it be?

How Pepsales AI Helps

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Pepsales AI empowers sales teams targeting engineering leaders to run deeper, sharper discovery conversations. It delivers smart, role-specific, and tech-aware questions in real time designed for technical buyers like CTOs and VPs of Engineering.

What it delivers:

  • A proven library of technical discovery questions by persona, product type, and  industry
  • Adaptive prompts that shift based on role maturity, objections, or org complexity
  • Contextual coaching to help reps handle technical pushback with confidence
  • Discovery automation, so your team can focus on listening, not guessing

Whether you’re selling DevOps platforms, infrastructure automation, or internal tooling, Pepsales AI helps your team zero in on the real blockers and position your value clearly and credibly.

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Ready to Win Over Engineering Leaders with Smarter Discovery?

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