Enterprise Readiness Checklist

Enterprise Readiness Checklist

An itemized checklist to ensure your product meets the requirements of enterprise buyers.

Jay Allen's photo
Jay Allen
·Dec 25, 2022·

9 min read

Amazing product features and user experience are crucial to winning new clients – but they’re not enough to persuade buyers at large enterprise firms.

Those buyers need to know that your product can withstand disruption from external and internal factors and provide predictable business continuity.

Why is enterprise readiness so important?

Selling to enterprises requires a set of specific capabilities relating to security, compliance, scaling, resilience, and more.

Enterprise buyers might need to check these things off their list before they can even consider doing business with you. Your product is only “ready” (ie. viable) when it can meet all of the mandates of an enterprise buyer.

The risk of being ill-prepared

If your product isn’t quite ready, you’re likely to lose a sale to your competitors. Even if their product features and design pale in comparison to yours, they’re likely to win the sale – so long as they can provide the required assurances about security, compliance, resilience, and scaling.

And, on the rare occasion when you win an account without providing all of those assurances, you’re gambling with your brand’s reputation. Recovering from data breaches can take your customer months, if not years. If that happens on account of your product, you’re going to have a hard time keeping that account or winning many new ones.

The benefits of readiness

The benefits go beyond simply landing new accounts. When you can prove that your product is built to sustain an enterprise business’s security, compliance, and scaling needs, then the possibilities to upsell expand.

Readiness also gives you a chance to position your business as a serious contender, regardless of the size and growth of your organization.

The enterprise readiness checklist: Core aspects

There are six core categories to consider in your evaluation:

  • Security and privacy

  • Deployment flexibility

  • Compliance and reporting

  • Scaling and automation

  • Cost optimization and innovation

  • Resilience

Each of these categories provides a crucial vantage point for understanding your product’s strengths, limitations, and possibilities for growth.

Security and privacy

An enterprise business will have a security policy that mandates a baseline for software security. It’s likely this policy will be aligned with an industry standard such as OWASP Application Security Standard and NIST Secure Systems and Applications.

It’s vital for software to meet the enterprise security baseline so it doesn’t become the weak link in their security posture.

An enterprise security baseline will demand that software can demonstrate capabilities in each of the following requirements:

  • Encryption of data in-transit and at-rest.

  • Front-end protection against CSRF, XSS and SQL Injection attacks.

  • Software supply-chain protection using Software Bill of Material.

  • Defense-in-depth

  • Identity and access management

  • Data protection

  • Detection and reporting

SaaS products have an advantage over traditional software. The cloud enables a shared responsibility model, enterprise-ready build, and deploy solutions.


  • Does your product offer sophisticated security methods to thwart external attacks like multi-factor authentication, role-based access control (RBAC), and SSO capabilities?

  • Does your product offer extensive audit logging capabilities for event logging and anomalous activity detection within your applications?

  • Does your product adhere to regional data privacy laws and regulations like GDPR and CCPA?

Being able to show formal evidence of compliance with these security requirements and privacy regulations will differentiate your product as seriously committed to these aspects.

Deployment flexibility

Your product needs to be able to be deployed in a wide variety of different environments, including across clouds, hybrid architectures, customer VPCs, and more.


  • Do you have reliable, predictable processes for deploying your software in a customer cloud or in a hybrid environment?

  • Can you deploy cross-cloud?

  • Are deployments version-controlled and managed across to secure processes?

Compliance and reporting

Enterprises have internal compliance standards and will likely also have external compliance requirements, especially in regulated industries. This is often a big difference between them and small businesses and startups.

No enterprise will deploy blackbox software into their landscape. Software that has a compliance badge on the box but can’t demonstrate compliance and can’t report on compliance status will not be seen as enterprise ready.

Internal compliance can be “is this software built to our standards”, “is this software being used to our standards” and reporting both on-demand and scheduled should be able to answer these questions.

Compliance questions

For software, common enterprise compliance questions can be:

  1. Standard secure deployment process - Is the software built and deployed using standards? Report on software that does and does not comply.

  2. Configuration drift - Is the running software the same configuration today as it was when originally deployed?

  3. Audit - is the software built using self-documenting stacks, or is it manual Word-like documentation that is often out of date?

Using a modern build and deployment solution is key to compliance reporting because it “shifts-left” these capabilities into the software process. The poor alternative is manual “after the fact” documentation, which although is common in enterprises, it’s something enterprises want to fix.


  • Do your customers rely on a compliance accreditation standard for their partners to adhere to? Think SOC2 or ISO27001.

  • Do your customers require a certain SLA baseline for reporting and fixing downtime issues?

  • Do they have data residency or data loss prevention requirements that your product can offer assurances for?

Scaling, automation and performance efficiency

Software vendors can use cloud well-architected frameworks, all of which have a pillar called performance efficiency. This category lists application best practices for scaling and automation for enterprise readiness:

  • Autoscaling

  • Caching

  • Batch processing

  • Decoupling and queues

  • Content-delivery networks

  • Data partitioning

A key aspect of deployment flexibility is automation. Enterprises look for automation because they don’t want to manually adjust for scale. It’s too slow and humans make errors, even the highly professional cloud providers make these mistakes. Having to raise a support ticket to add users or deploy more containers is not scalable or automated.


Software is more enterprise-ready when it can automatically scale in four directions:

Scale out

Add more application containers to increase resources

Scale up

Add more cpu, memory to a container to increase resources.

Scale in

Destroy containers to decrease resources.

Scale down

Reduce cpu and memory to decrease resources.

Software needs to be architected to cope with these scaling features, and it needs the systems around it in run time to have deployment flexibility to trigger the events based on demand.


  • Does your product provide flexible deployment options to multiple platforms using Infrastructure as Code (IaC)?

  • Does your product provide observability and automation opportunities to instrument key events to prevent downtime and scale to new instances? Think DevOps automation.

  • Does your product allow auto-scaling options to handle peak workloads while optimizing resource efficiency?


The AWS Well-Architected Framework defines resilience as:

“Resiliency is the ability of a workload to recover from infrastructure or service disruptions, dynamically acquire computing resources to meet demand, and mitigate disruptions, such as misconfigurations or transient network issues.”

There are many factors that can make cause software to fail:

  1. Human operator error.

  2. Configuration drift.

  3. Failing components aren’t observed or restarted.

  4. Exhausted resources due to failure to scale up.

  5. Cascading failures.

  6. Facility outage including network and power.

  7. Bad actors including ransomware.

Outages cost money for every business, but for large enterprises the blast radius of an outage is much larger. For this reason, enterprises will want to see how the software and the build, deployment, and run services demonstrate resilience.


Beyond the internals of the software, enterprises always check a product’s systems:

  • Is the software architected using resiliency techniques as directed by cloud well-architected frameworks?

  • Are resiliency best practices embedded into the build and deployment software?

  • Are the build, deployment and run services resilient in themselves?

Enterprises will have more confidence in resiliency when they can see it is robust, automated, proven, best practice and demonstrable.

Cost optimization and innovation

Cost optimization for software means continuously adjusting the resources it requires. This means that the software needs to be “wrapped” in a build, deployment and run system that can adjust the resources that the software uses, and therefore optimize the costs.

“Cost optimization is a continual process of refinement and improvement over the span of a workload’s lifecycle.”

Cost optimization relies on rapid build-and-deploy solutions plus automation to scale up/out and then scale back down/in on-demand.

An enterprise will look for the software and its support systems to deliver cost optimization through:

  1. Use Infrastructure-as-Code to document the resources actually used, and refine them over time based on usage data.

  2. Use automation to scale up/out and down/in on-demand.

  3. Be able to deploy new stacks with different cost profiles.

Cost-optimization is mostly about the systems that support the software rather than internal application code, though of course application architecture is important for cost optimization as detailed in all cloud hyperscaled well-architected frameworks.


  • Does your product enable the discovery of new data sets or show adoption usage metrics across the enterprise?

  • Do you and your customers have cost transparency, so you can see what’s actually getting deployed in a customer’s account?

  • Does your product provide insights on which parts of the enterprise spend more time and resources within a specific domain? For example, approval cycles within a contracting department.

  • Does your product provide usability improvements to nudge for better acceptance and usage of the product for productivity? Think about surfacing potential cost savings by switching to an annual consumption-based infrastructure tier.

Tips for implementing the enterprise readiness checklist

You now know the defining aspects of an enterprise readiness checklist. But how do you get the organization to rally behind making our product and offering enterprise-ready?

The following section provides tips in three key areas:

  • Leadership

  • Collaboration

  • Transparency

Align your leadership with the purpose

As a result, getting your leadership aligned on becoming enterprise-ready will be the primary success factor for running and executing this checklist. Try to ensure that you can address all concerns and queries from your organizational leadership before implementing this checklist.

Collaborate on the enterprise readiness audit

The idea of an audit can easily make people nervous. After all, it’s looking for gaps in performance – and no one wants to be blamed for that. At the same time, you need everyone to participate in order to conduct a truly exhaustive audit.

Helping teams understand why we are evaluating enterprise readiness would alleviate their concerns and motivate them to honestly introspect on key improvement areas and align them to the overall mission.

Make the process transparent for all stakeholders

As you take stock of your enterprise readiness gaps, you should consistently share the results of your assessment with your leadership and all relevant stakeholders.

The more information team members have on making resilient products, the more empowered they’ll be to make necessary changes.

Making enterprise readiness easier

Don’t let complex deployment processes slow your customer adoption. TinyStacks lets you automate customer deployment, version management, and monitoring to any cloud with infrastructure as code. TinyStacks lets you:

  • Templatize your app and its infrastructure so you can deploy to customer VPCs in hours, not weeks

  • Host single-tenant cloud instances for customers with automatic VPC peering support.

  • Add multi-cloud capability to your app so you can support customers on any cloud.

  • Get you a single view into your customer deployments across clouds, regions, and versions.

Schedule a demo with us today to learn how we can help.

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