I recently caught up with a former co-worker who now runs an information security program for a well-known retailer. While discussing new advances in cloud security and technology, he mentioned that his company had met with a provider that presented him with a mind-numbing number of deployment options for their solution. Some of the options rattled off included forward and reverse proxies; public, private, hybrid, and cloud versions of their product; an on-premise version; and packaging in an appliance or a box that could be racked in a data center.

Undoubtedly, a list of options this long provides increased flexibility to deploy solutions in a way that makes the most sense on a company-to-company basis. However, as deployment options increase, so does the complexity of creating a successful plan for deployment. In the list below, I'll provide helpful tips for balancing the aforementioned flexibility and complexity that make up the cloud security deployment space today.

1. Create a functional checklist
When selecting a cloud security solution, it's essential to identify which functions are most important to the company. For example, some organizations want visibility into activity in their cloud applications. Others want to protect against leaks of sensitive data and other security threats from both inside and outside sources. Some companies are especially concerned with regulatory compliance - the list goes on.

I suggest documenting fundamental criteria in a checklist because it offers a clean way to assess multiple providers and identify which is the best fit.

2. Select a deployment topology that maximizes coverage and minimizes user disruption
Theoretical deployment topologies can be ineffective. Your provider needs to give you documented evidence that the proposed topology has been tested and validated with other clients (ideally with similar requirements). Check with your network and industry analysts as well as your provider's references, being sure to ask questions about why they chose a particular topology, the trade-offs, and the impact to end users.

Security solutions have a reputation for not being business-friendly because of their invasive nature. Have an understanding of how your deployment will affect different user communities. For example, if you roll out a user monitoring solution for Salesforce CRM, you should evaluate the effects on:

• Sales reps who use Salesforce CRM
• Salesforce admins who manage and configure the service
• Security analysts who will use the monitoring solution
• Security executives who are responsible for oversight of all security issues
• The application LoB executive who sponsors the purchase of the CRM service.

3. Have a clear on-boarding plan with success criteria
When adopting a solution, make sure that your provider creates an on-boarding plan that addresses all major aspects of your cloud security requirements. The provider needs to break down the on-boarding plan into phases with milestones, as well as clearly document test cases and success criteria for each phase. The plan should list all dependencies for each success factor and identify whether they or you are responsible for each.

4. Insist on an annual success roadmap
Annual success roadmaps are critical because they document the usefulness of the service and identify value on an ongoing basis. In addition to proposing new capabilities, the roadmap should plan for any training required, quantify the extent to which the provider delivered on the value proposition, and identify areas for improvement. I suggest reviewing the roadmap quarterly and updating it as the organization's needs evolve. You may also want to ask for a dedicated customer success professional to be assigned to you.

Each cloud security journey will be unique, while also sharing attributes with others that have taken or are taking the same path. Understand and benefit from the lessons that companies have learned in the past. While having flexibility is great, having a clear path for your journey is even more valuable.

Important questions include: Does the solution change the behavior of users of the cloud service? Does it require installing agents on users' devices? Will it introduce performance or latency issues? What happens if the solution has an outage or downtime?

After identifying a deployment topology, test it in sandbox mode. The beauty of SaaS and cloud deployments is that most providers can offer a sandbox mode for testing the topology with appropriate use cases. If the provider does not offer a sandbox mode, it's probably a red flag.