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8 Steps to Cloud Success:  A Cloud Roadmap is the Path to Business Agility

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8 Steps to Cloud Success : 

A Cloud Roadmap is the Path to 
Business Agility

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About Sand Hill Group

 (http://sandhill.com) provides strategic management, 

investment, and marketing services to emerging market leaders. Sand Hill 
Group is best known for its work in the $600-billion software and services 
market. As founder of the “Enterprise” and “Software” conference series, Sand 
Hill Group has been credited with uniting the software business ecosystem 
of executives, entrepreneurs, investors, and professionals. The firm is also 
the publisher of SandHill.com, the premier online destination for business 
strategies for the software, cloud, and mobile ecosystem. The site and its 
newsletters are read by thousands of top software industry executives as well 
as CIOs and IT buyer executives. Sand Hill Group also funds primary research 
into key technology and business model trends that impact business in the 
software, cloud, and mobile ecosystem.  

This paper was made possible by SAP

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8 Steps to Cloud Success:  A Cloud Roadmap is the Path to Business Agility

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8 Steps to Cloud Success 

A Cloud Roadmap is the Path to Business Agility  

CIOs participating in Sand Hill Group’s study (see Appendix) stated 

unanimously that the primary driver for moving to the cloud is to meet business 

needs. More than the dollar savings that cloud computing brings to the table, one 

of the most important intangible benefit is that the cloud enables companies to 

do things they conceivably could not do in the pre-cloud era. 

As an example, a company may want to test a new idea that could be a 

breakthrough innovation for its business, but it requires 100 new servers to 

even start the evaluation process. In the pre-cloud days, that type of expensive 

constraint could result in giving up on the idea before evaluating it. But today, in 

the cloud, a company just needs a credit card to get started; and testing costs are 

so insignificant that they might not even need budget approval.

As the cloud enables business agility, the case for cloud computing adoption is 

compelling. The ability to ramp up and ramp down computing power quickly 

delivers a competitive advantage and saves money that was traditionally spent 

building overcapacity.

But transitioning to the cloud involves a significant amount of business process 

and culture change. What are the most important steps in achieving a successful 

transition? What should a company’s cloud strategy and roadmap look like? 

This paper explains eight steps for successfully transitioning to the cloud: 

1.  Adopt a progressive mindset

2.  Watch, learn, and experiment

3.  Demonstrate quick wins 

4.  Develop a business case 

5.  Understand the risks 

6.  Analyze the current IT portfolio 

7.  Create a vision of the end-state 

8.  Develop and execute the roadmap 

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Step 1: Adopt a Progressive Mindset 

Success in transitioning to the cloud depends on adapting to change. Thus, the 

first step in a cloud computing strategy and roadmap is for the company—both 

management and employees—to adopt an open, progressive mindset regarding 

the application of new technologies to gain business benefits. 

Transforming a company’s business using cloud solutions is not just about 

technology adoption and implementation. It also involves broader business 

and operational changes in several areas including governance, budgeting, 

contracting, regulatory compliance, polices, people, and processes. Thus, the 

move to cloud computing involves changing mindsets, cultural patterns, process 

patterns, and colleagues’ hearts so that they willingly adapt to new approaches 

and technologies. 

Spearheading disruptive change in the organization will be the most difficult 
part of the journey.

Machiavelli said this about change more than 500 years ago: “There is nothing 

more difficult to take in hand, more perilous to conduct, or more uncertain in its 

success, than to take the lead in the introduction of a new order of things.” 

Understanding the cloud’s power and potential is certainly important; but 

getting mentally ready to take the plunge can be a stumbling block. The 

underlying reasons—perceived or real—are many: 

•  Fear of the unknown 

•  Fear of loss of control

•  Fear of job loss 

•  Risk aversion 

•  Lack of tolerance for change 

Successfully transitioning to the cloud requires a company’s top management 

to drive change in order to ultimately generate value for customers and 

shareholders. Management needs to educate and convincingly explain to 

everyone in the company what the company is doing, why the new approaches 

bring value to the company, and who will be impacted—and how—by the 

change.

“Use of the cloud in our industry is an exception rather than the norm. I think a lot of 

companies in more traditional, mature industries like ours are missing out on a lot of 

opportunities to take advantage of what the cloud has to offer. I would encourage these 

companies to be open-minded and progressive and look at alternatives to traditional, 

client-server, on-premise systems.” – CEO, manufacturing company 

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Step 2: Watch, Learn, and Experiment 

Embracing any new technology involves learning. Sand Hill’s 2010 “Leaders 

in the Cloud” research study (see Appendix A) found that companies typically 

conduct experiments to see how the cloud really works and how it fits or doesn’t 

fit into the requirements of the business. Through this process, companies 

became familiar with constraints, issues, and benefits of the technology. 

Many of Sand Hill’s surveyed executives described this testing phase as similar 

to that of adopting outsourcing services: experiment with nonstrategic projects 

to acclimate the company to a new way of doing business, evaluate selected 

vendors, and assess business benefits. As their companies experienced the 

benefits and understood the technology, their outsourcing initiatives matured 

successfully and gained a significant share of projects. 

Some companies also take advantage of experimenting with private clouds until 

they believe public clouds become more secure. A CIO at a Fortune 500 company 

participating in the Sand Hill survey on transitioning to mobility (see Appendix) 

commented that they placed their catalogue of services (a store-like environment) 

in the cloud so that it would scale efficiently across all modes of access. Their 

initial experiment was in a private cloud while waiting for two years for the 

public cloud to become more reliable.

Step 3: Demonstrate Quick Wins 

Many companies participating in the Sand Hill survey set up innovation 

sandboxes, referred to as Skunk Works projects, where their project teams were 

allowed to work with the new cloud technology within the context of a specific 

business initiative. 

Here are some examples of such small, experimental projects that companies in 

the study executed in the cloud: 

  Initiated development projects where small teams work on specific 

business-driven projects on a public Infrastructure-as-a-Service (IaaS) 

cloud such as Amazon. Examples of these projects include a short-term 

marketing campaign, IT resources for offshore developers, and a new 

website for photo sharing. 

  Developed a small tactical application on a Platform-as-a-Service (PaaS) 

cloud such as Force.com or Windows Azure. Because the platform is so 

easy to use and does not require any programming knowledge, a CIO of a 

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manufacturing company developed a simple HR application in less than 

a week. He said this would have taken several months for a professional 

technical developer using traditional platforms. 

  Acquired a Software-as-a-Service (SaaS) application for a non-mission-

critical business process. An executive in a media company rolled out 

a cloud-based e-mail system to hundreds of users in less than a month. 

Based on high user satisfaction ratings of this new e-mail system, the 

company decided to roll out the e-mail system to all of its users. 

When the companies successfully completed these projects in much shorter 

timeframes and with less effort than it would have normally taken, they then 

pushed the results up the value chain and funded new pilot projects. The Sand 

Hill study found that many companies used the cloud to solve specific and 

tactical problems and, for the most part, achieved successful results. 

At the next stage of getting to the cloud, however, companies need to develop 

a business-case-driven cloud strategy that is fine-tuned by findings and value 

gained from the tactical projects. The emphasis needs to shift at this stage from 

“how” to more of “what” and “why.” Otherwise, short-term, tactical projects 

will dominate the transition to a cloud-based IT reality, which won’t necessarily 

generate global business value or, even worse, will end up with vendors driving 

the company’s agenda. 

Step 4: Develop a Business Case 

Companies should consider the following fundamental business drivers when 

building a business case for cloud computing: 

•  Business agility:

 Identify how to apply cloud applications and platforms 

to the business, enabling better and faster competitiveness. 

•  Operational excellence:

 Investigate how cloud solutions can lead to 

improved availability, reliability, and lower total cost of ownership (TCO), 

enabling the company to invest the savings back into the business. 

“I have never established a cloud computing strategy or issued a mandate that 

everything needs to go off premise or move to some type of hosted model. The driver 

behind it is a business need defined and executed by line-of-business stakeholders.”

– CIO, healthcare company 

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Like any other emerging technology, the fundamental decision to embrace cloud 

computing comes down to figuring out how the investment in the cloud will 

yield positive returns to the business at an acceptable risk level. The following 
CIO comment from an interview in the Sand Hill study is a good example:

If a company uses a public cloud for solving specific business problems, the 

business case also becomes an outsourcing decision—one where the company 

also looks for value in solutions that are safer, less expensive, and better than 

what it can create by itself. 

In the past few years, public cloud solutions have improved, becoming more 

robust and also more compelling in quality, stability, and overall cost-to-benefit 

ratio. 

Many commodity services (e-mail, backup, archival, collaboration, etc.) are now 

available as public cloud services. Other commodity services now available in 

the cloud include the following standard business processes: 

•  Customer relationship management (CRM) 

•  Expense management 

•  Accounting 

•  HR management 

•  Manufacturing, wholesale, and professional services components 

•  ERP (especially beneficial for fast-growth companies) 

For each business problem a company seeks to solve, it needs to look at a 

cloud solution and compare it with alternative solutions from both return on 

investment (ROI) and TCO perspectives. 

Step 5: Understand the Risks 

Like any new technology that offers credible business value, there are also risk 

factors to consider. Risks around security, privacy, and governance are major 

concerns for nearly every company. Sand Hill’s “Leaders in the Cloud” 2010 

research study found a broad range of attitudes about security, privacy, and 

governance. 

“We have an opportunity to do 10 times greater energy efficiency inside our data center 

than what we are doing today simply by adoption of the private cloud. Our goal is to 

take 20 percent of data center running costs away from the fully loaded costs including 

facilities, energy, hardware, software, maintenance, headcounts, consultancy. That’s 

close to $200 million dollars savings for us annually and a significant chunk to take off 

the bottom line.”

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Security concerns vary greatly by company—depending on the following factors:

  Business goals and rewards 

  Perceived or real risks 

  Level of risk tolerance 

  Value and sensitivity of information assets and data 

  Regulatory concerns 

Sand Hill’s survey of IT executives found large enterprises were more concerned 

about data privacy, security, and governance issues than smaller companies 

(see Exhibit 1). Most of the small and midsize enterprise (SME) IT leaders were 

emphatic that a cloud vendor’s security processes must be superior to any that 

their own company could provide. The reason: SMEs’ cost structures are such 

that they cannot afford to build secure infrastructures that match those of large 

enterprises or the leading cloud vendors. 

Exhibit 1:

 

Comparison of large and small companies’ 

concerns about cloud computing

Source: Sand Hill Group Cloud Computing Survey 2012

“Large enterprises” refers to companies with $20 billion or more in revenue.  “Small and midsize 

enterprises” includes companies with less than $500 million in revenue.

Large

Enterprises

Small and 

Midsize 

Enterprises

Data privacy

63%

53%

38%

33%

25%

23%

15%

5%

0%

3%

46%

36%

28%

47%

25%

19%

7%

18%

11%

2%

Developers/corporate culture
Lack of practical experience with cloud computing
Migration/interoperability
Lack of standards
Regulation

No barriers
Don’t know

Lack of development and monitoring of service-level 

aggreements (SLAs)

Governance (e.g., policies for control, security, 

monitering and services)

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Among many examples of surveyed business executives who were pleased 

with the security of their cloud vendors is the following statement from a 
manufacturing company executive: 

However, vendors can fail. A recent high-profile example is Amazon’s failure in 

April 2011, which resulted from a configuration error. What would happen to a 

customer’s data in that case? Would the provider return the data, or would it be 

lost forever? The good news is that companies that properly understood their 

cloud vendor’s offering made sure they included data backups and redundancies 

in their applications. They also conducted due diligence to ensure they properly 

understood the vendor’s offerings, service level agreements (SLAs), and 

architecture. Such companies remained unscathed and ran their operations 

without any interruption during the Amazon outage. 

Many vendors are getting certified to security standards such as SAS 70. 

However, even if a vendor is certified, the most important question to ask is: 

does the certification meet your specific security requirements? As one surveyed 

executive stated:

Step 6: Analyze Your Existing IT Portfolio 

Another important step in the roadmap of getting to the cloud is performing an 

inventory of the company’s current IT systems and developing a logical model 

of the existing architecture including all relevant systems, data, applications, 

processes, functional components, and services. As part of this exercise, the 

company should ask the following questions and analyze the systems from these 

perspectives: 

“You should really ask for a security review, especially if you are a big company dealing 

with a smaller company and the risk to you is greater than the risk to them in case of a 

security breach. On the other hand, if you are a small or medium-sized business, your 

risk is much lower if you are dealing with a well-established large cloud vendor such 

as SAP, Salesforce, Amazon, or Microsoft, that is betting their business on their cloud 

services.”  – Principal consultant, leading security firm 

“We have been using SaaS applications for more than nine years, and we haven’t had 

a security breach so far. At the end of the day, we are very vigilant about security, 

including strong passwords and frequent password updates; and we audit usage 

patterns of our users to monitor for any untoward behavior.” – CEO, manufacturing 

company 

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  What is working and what is not? 

  What is core to the business and what is not? 

  What is driving innovation and what is preventing progress? 

  Where are the cost efficiencies and inefficiencies? 

  What is driving business value and what is not? 

  How are the systems coupled and interoperating with each other? 

This analysis not only provides a snapshot of the company’s current state of IT, 

but also delivers crucial information to help fine-tune its business case based on 

the new architecture. 

Without doubt, the cloud deployment options in the architecture will drive down 

cost inefficiencies and improve agility and scalability, among other benefits. 

Analyzing an existing IT portfolio in this manner typically takes no longer than 

four to six weeks in a midsized company. 

Step 7: Create a Vision of the End-State 

Once the company has a clear understanding of the current state of its IT 

portfolio, the pain points, and the cost inefficiencies, it can then begin to map out 

the vision of moving purposely to the end-state. That end-state description will 

include the following aspects: 

  Which architectural components, data, applications, systems, services, 

and processes will move to the cloud and in what order?

  How much decoupling will be required to isolate the components? 

In designing the end-state vision, the company needs a reference platform that 

leverages cloud technologies for highly scalable automation, low-cost hardware, 

middleware, and application servers to connect new and existing applications. 

Such an analysis will consider not just the technology piece, but also the people, 

process, and cost aspects including the most important areas such as budgeting, 

TCO, service level agreements, governance, and compliance. 

The Sand Hill study found that, even if the cost of moving to the end-state from 

the current state is $5 million (for example), most small to midsize companies 

will move ahead with the initiative if the end-state generates cost savings of more 

than, say, $10 million per year. 

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Step 8: Develop and Execute the Roadmap 

After creating a vision of the end-state, the company then needs to determine 

which applications and data to move when, and where, before detailing the 

specifics around how to move them. It is not necessary or practical to move 

everything all at once. 

Create a roadmap for a long-term perspective (say, three years) and map out how 

the architectural components will move over in a staged manner to a much more 

effective, efficient architecture. This roadmap exercise should include a cost-and-

benefit analysis for each stage of the roadmap. 

Typically, companies focus on the “low-hanging fruit” with the most business 

value and place those components on the roadmap first. For example, companies 

initially select a relatively less-critical application that is currently not running 

cost-efficiently in-house. Moving it to an external cloud quickly will create 

significant business value. As a next step, they then select the less-valuable and 

more risky systems that are still worth moving, and place them at the back end of 

the roadmap. 

Another consideration is to review the project portfolio, and identify new and 

innovative revenue-generating projects that will benefit from a faster time-to-

market advantage using cloud technologies. 

For each of the identified applications, the company needs to evaluate a cloud 

vendor’s offering to ensure that it meets the security, scalability, reliability, data 

privacy and governance needs of the enterprise and meets established security 

and compliance (SAS 70, FISMA, ISO/ IEC 27001, PCI, and HIPAA) standards. 

This evaluation includes: 

  Review the vendor’s SLA provisions based on the company’s specific 

business risks, risks that typically may not be covered in standard SLAs. 

  Identify changes required in the vendor’s data compliance and security 

procedures (if any) to adapt to the company’s risk, compliance, and 

business metrics. 

  Identify interoperability, lock-in, and compatibilities issues and determine 

workarounds as applicable. 

  Carry out a hands-on product and technology validation and evaluation 

against the above criteria. 

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  Assess the company’s financial stability and longevity. 

  Evaluate the company’s commitment to innovating with its customers. 

  Obtain examples of customers’ successes. 

Conclusion 

Transitioning to the cloud is similar to a major change initiative and needs 

top management support, clear vision, and careful planning. The eight steps 

presented here are sequenced in a logical order designed to yield maximum 

value. Typically, the more detailed activities of later steps provide additional 

information that helps companies fine-tune and refine the results of previous 

steps. In this sense, this is an iterative and cyclical process that companies can 

apply throughout the IT life cycle. 

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APPENDIX A 

Overview of Sand Hill Group Studies

The information in this paper is based on six studies conducted by Sand Hill 

Group in 2010-2012, as follows:

1.  “Leaders in the Cloud: Identifying the Business Value of Cloud Computing 

for Customers and Vendors” (March 2010).  This landmark research study 

identified the business value realized by companies deploying cloud-

computing initiatives. The two-phase study design utilized 40 one-hour 

interviews to uncover insights from customer and vendor experiences, and a 

quantitative market survey with 511 participants provided a snapshot of cloud 

initiatives and priorities at a variety of companies. The interviews and survey 

questioned respondents about their current cloud initiatives, current and 

planned use of specific cloud models, business benefits, organizational and 

technical challenges, and details of specific use cases.

2.  “Leaders in the Cloud: The Changing Tide: (March 2011). This study gauged 

software vendors’ cloud outlook for the coming year and beyond. The study 

utilized an online survey with 100 participants supplemented with in-depth 

follow-up interviews of 10 percent of the participants to gather executives’ 

impressions on the direction of the cloud market, their cloud strategies, and 

customer readiness for adoption. 

3.  “Software CEO Outlook 2010: New Decade, New Realities” (April 2010). This 

study, comprised of a survey and follow-up in-depth interviews, focused 

on the opinions of 107 software CEOs and CFOs regarding the changes in 

software products, business models, and pricing models due to changing 

customer expectations and the adoption of cloud computing. 

4.  “Software CEO/CFO Outlook 2011: The Gains and Pains of Growth” (April 

2011). This study, comprised of a survey and follow-up in-depth interviews, 

focused on the opinions of 119 surveyed software CEOs and CFOs regarding 

the future state of the software industry. Questions included a focus on cloud 

and mobile solutions. 

5.  “Leaders in Enterprise Mobile Strategies: Tug of War Between Business Value 

& Risk” (November 2011). This study looked at the value-generation benefits 

and the challenges of transitioning to enterprise mobility. The survey of 53 

enterprise executives and an additional 20 in-depth interviews of enterprise 

CIOs, CISOs, and vice presidents, uncovered mobile strategy pitfalls, best 

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practices, cost analyses, and a roadmap. Study participants also provided 

information about their companies’ use of cloud computing to enable their 

mobile applications.

6.  “Job Growth in the Forecast: How Cloud Computing is Generating New 

Business Opportunities and Fueling Job Growth in the United States” 

(December 2011). This research study uncovered several aspects of how 

companies of all sizes are leveraging cloud computing solutions for 

competitive advantages.

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Copyright 2012 Sand Hill Group

The information contained herein has been obtained from sources believed 

to be reliable. Sand Hill Group disclaims all warranties as to the accuracy, 

completeness or adequacy of such information. The Sand Hill Group shall have 

no liability for errors, omissions or inadequacies in the information contained 

herein or for interpretations thereof. The reader assumes sole responsibility for 

the selection of these materials to achieve its intended results. The opinions 

expressed herein are subject to change without notice. Reproduction of this 

report in print or electronic form is strictly prohibited without written permission 

from Sand Hill Group.