The CTO's Guide to Managed Security & DevOps
Technical evaluation framework for assessing managed service providers. Architecture fit, security posture, team collaboration, and technology stack considerations.
Key Questions CTOs Ask
The technical concerns that matter when evaluating managed service providers
Will this fit our architecture?
We work with cloud-native, hybrid, and legacy systems. Our approach is stack-agnostic with expertise across AWS, GCP, Azure, Kubernetes, and traditional infrastructure.
What's the security posture?
Zero Trust architecture, defense-in-depth, SOC 2 Type II compliance. 24/7 SOC with SIEM, EDR, and proactive threat hunting.
How does team augmentation work?
We embed with your team via Slack/Teams, participate in standups, contribute to PRs, and transfer knowledge systematically. Not a black box.
What's your technology stack?
Infrastructure as Code (Terraform, Pulumi), GitOps (ArgoCD, Flux), observability (Datadog, Grafana, ELK), security tooling (Wiz, Snyk, CrowdStrike).
How do you handle CI/CD integration?
We integrate with your existing pipelines (GitHub Actions, GitLab CI, Jenkins) and add security scanning, compliance checks, and deployment gates.
What about observability?
Full-stack observability with metrics, logs, traces, and APM. We implement SLOs, error budgets, and actionable alerting without noise.
Technical Evaluation Criteria
Deep-dive into the technical capabilities you should validate before committing
Security Architecture
Key Requirements
- Zero Trust network design
- Defense-in-depth layers
- Secrets management (Vault, SOPS)
- Identity & access management
- Encryption at rest and in transit
- SIEM with threat intelligence
How to Evaluate
- Request architecture diagrams
- Review incident response playbooks
- Validate compliance certifications
- Test security automation
Infrastructure as Code
Key Requirements
- Version-controlled infrastructure
- Immutable infrastructure patterns
- Automated drift detection
- Multi-environment management
- Disaster recovery automation
- Cost optimization automation
How to Evaluate
- Review IaC repositories
- Check PR review process
- Validate testing practices
- Assess rollback procedures
GitOps Practices
Key Requirements
- Git as single source of truth
- Automated deployments
- Progressive delivery (canary, blue-green)
- Automated rollbacks
- Audit trail for all changes
- Policy enforcement (OPA, Kyverno)
How to Evaluate
- Review deployment workflows
- Check policy enforcement
- Validate RBAC implementation
- Test rollback scenarios
Observability Stack
Key Requirements
- Metrics, logs, and traces unified
- SLO/SLI implementation
- Distributed tracing
- Real-user monitoring
- Custom dashboards per service
- Intelligent alerting (no noise)
How to Evaluate
- Request sample dashboards
- Review alerting philosophy
- Check on-call processes
- Validate cost management
Container & Orchestration
Key Requirements
- Kubernetes expertise
- Service mesh implementation
- Container security scanning
- Resource optimization
- Multi-cluster management
- Helm/Kustomize patterns
How to Evaluate
- Review cluster architectures
- Check security policies
- Validate upgrade processes
- Assess HA/DR capabilities
CI/CD Integration
Key Requirements
- Pipeline security scanning
- Automated compliance checks
- Artifact signing & verification
- Environment promotion gates
- Test automation integration
- Deployment approval workflows
How to Evaluate
- Review pipeline templates
- Check security scanning
- Validate test coverage
- Assess deployment velocity
How We Work With Engineering Teams
Embedded collaboration, not outsourced black box. We work alongside your team, not instead of them.
Onboarding (Week 1-2)
- Architecture review & documentation
- Access provisioning & security setup
- Tool integration (Slack, Git, ticketing)
- Team introductions & workflow alignment
Knowledge Transfer (Ongoing)
- Comprehensive documentation in your wiki
- Regular architecture decision records
- Lunch & learns on security/DevOps topics
- Pair programming & PR reviews
Daily Collaboration
- Participate in team standups
- Contribute to sprint planning
- Code reviews & architecture discussions
- Incident response & postmortems
Continuous Improvement
- Quarterly architecture reviews
- Security posture assessments
- Performance optimization sprints
- Technology radar & recommendations
Code in your repositories
Coverage without on-call burden
Average incident response time
Technology Stack & Expertise
Battle-tested tools and platforms we use to build and secure your infrastructure
Cloud Platforms
- AWS (EKS, ECS, Lambda, RDS)
- Google Cloud (GKE, Cloud Run, BigQuery)
- Azure (AKS, App Service, Cosmos DB)
- Multi-cloud & hybrid architectures
Container & Orchestration
- Kubernetes (all major distributions)
- Docker & containerd
- Helm, Kustomize, ArgoCD, Flux
- Service mesh (Istio, Linkerd)
Infrastructure as Code
- Terraform (certified experts)
- Pulumi (multi-language IaC)
- CloudFormation, ARM templates
- Ansible, Chef (legacy support)
Security Tools
- Wiz, Snyk, Aqua Security
- CrowdStrike, SentinelOne
- HashiCorp Vault, AWS Secrets Manager
- SIEM: Splunk, Elastic Security
Observability
- Datadog (preferred), New Relic
- Grafana, Prometheus, Loki
- ELK Stack, OpenTelemetry
- PagerDuty, Opsgenie
CI/CD
- GitHub Actions, GitLab CI
- Jenkins, CircleCI, Buildkite
- Spinnaker, Harness
- ArgoCD, Flux for GitOps
Databases
- PostgreSQL, MySQL, MongoDB
- Redis, Elasticsearch
- Cloud-native (Aurora, Cloud SQL, Cosmos)
- Database migration & optimization
Networking
- VPC design, transit gateways
- Load balancers (ALB, NLB, GLB)
- CDN (CloudFront, Cloudflare)
- VPN, Direct Connect, ExpressRoute
The Case for Technical Leadership
Why managed services free you to focus on strategic initiatives that create competitive advantage
Focus on Product, Not Plumbing
Your team builds features that differentiate your product. We handle infrastructure, security, and compliance work that doesn't create competitive advantage.
60-80% more engineering time on core product
Accelerate Without Adding Headcount
Scale operations without the 3-6 month hiring cycle. Get senior-level expertise immediately without recruitment, onboarding, or retention overhead.
90 days faster time-to-capability vs hiring
Enterprise Security Without Enterprise Cost
SOC 2, ISO 27001, PCI DSS, HIPAA expertise without building a security team. We've done this dozens of times and know every pitfall.
$300K-800K saved vs building security team
Battle-Tested Practices
Patterns proven across 50+ companies. We bring institutional knowledge from incident response, scaling challenges, and compliance audits.
Avoid 12-18 months of trial and error
24/7 Coverage Without Burnout
Round-the-clock monitoring and incident response without destroying your team's work-life balance. We handle 3am pages.
Zero on-call burden for your engineers
Technology Radar & Future-Proofing
We track emerging tech, security threats, and compliance changes. You get proactive recommendations, not reactive firefighting.
Stay ahead of technology curve
Red Flags When Evaluating Providers
Warning signs that should make you think twice before signing a contract
Lack of Technical Depth
Sales team can't answer architecture questions. No certified engineers on staff.
What to look for instead: Ask to speak with actual engineers who will work on your account. Request certifications.
Proprietary Lock-In
Everything built on proprietary tools. No standard IaC or GitOps practices.
What to look for instead: Insist on infrastructure-as-code in your Git repos. Avoid vendor-specific tooling.
Black Box Operations
No visibility into what they're doing. Documentation kept in their systems only.
What to look for instead: Demand documentation in your wiki, code in your repos, transparency in all work.
Offshore-Only Teams
No US-based engineers. Communication happens only via tickets.
What to look for instead: Ask about team locations, time zones, communication methods. Test responsiveness.
No Compliance Experience
They've never done SOC 2, ISO 27001, or your required framework before.
What to look for instead: Request case studies, certifications, and compliance team credentials.
Manual Processes
Still logging into servers, making manual changes, no automation.
What to look for instead: Ask about IaC coverage, automation level, and change management processes.
Slow Response Times
SLAs measured in hours or days, not minutes. No 24/7 coverage.
What to look for instead: Review actual SLA commitments. Ask about on-call processes and escalation paths.
Inflexible Pricing
Rigid packages that don't match your needs. Hidden fees for everything.
What to look for instead: Request transparent pricing. Understand what's included vs. additional cost.
Technical Evaluation Checklist
Use this checklist when vetting potential managed service providers
Technical Validation
- Review their IaC repositories and coding standards
- Speak with their senior engineers (not just sales)
- Request architecture diagrams from similar clients
- Test their incident response process
- Validate security certifications and compliance
- Check their technology radar and innovation track record
Collaboration Assessment
- Understand communication channels and frequency
- Review knowledge transfer and documentation practices
- Assess cultural fit with your engineering team
- Test responsiveness during sales process (indicator of future)
- Clarify decision-making authority and escalation
- Verify team stability and turnover rates
Business Terms
- Clear SLA definitions with penalties for misses
- Flexible contract terms (avoid 3-year lock-ins)
- Transparent pricing with no hidden fees
- IP ownership of all work product
- Reasonable termination clauses with transition support
- Insurance coverage (E&O, cyber liability)
Ready for a Technical Deep Dive?
Schedule a call with our CTO to discuss your architecture, security requirements, and how we can augment your team without disrupting your workflow.
Get a Free Security & Infrastructure Assessment
Understand your current security posture, identify critical risks, and get a prioritized roadmap for improvement.
What you'll receive
No commitment required. Assessment takes 48 hours. Report is yours to keep.
Assessment Preview
Areas we evaluate in your free assessment
Security Posture
A-F Rating
Infrastructure
Health Check
Access Controls
Gap Analysis
Vulnerabilities
Risk Score
Sample Report
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