Digital Transformation is a hot topic. A topic either loved or hated. In some organizations,
Digital transformation is the profound transformation of business and organizational activities, processes, competencies
https://www.i-scoop.eu/digital-transformation/and models to fully leverage the changes and opportunities of a mix of digital technologies and their accelerating impact across society in a strategic and prioritized way, with present and future shifts in mind.
As Rudy Giuliani said in 2008, “change is not a destination, just as hope is not a strategy”, digital transformation illustrates change and the hope change improves the business. A strategy and a destination
The purpose of this article is to offer the beginnings of a strategy for user and application rationalization, enhanced security, and enhanced
What is a Mid-Sized company?
According to the Business Journal, mid-sized companies are companies from 100 to 500 employees and account for 2.1% of businesses in US major metropolitan areas1. Two percent may not seems like a lot. In the sheer number of companies, as compared to small businesses, it’s not. My hometown of St Louis hosts 1,500 whereas New York City is home to roughly ten thousand.
Depending on your industry and your revenue the Small Business Association is likely to categorize these Mid-Size businesses as Small Business2. An example would be a caterer which has 200 employees and generates five million dollars annually, by SBA definition, would be a small business. In order to understand the digital transformation needs of a particular business, we need to segment them a bit more. My Say summed it up nicely in Forbes, “A two-person shop has a radically different perspective than a 200-person operation, on just about every topic.” 3 For the purposes of this article I will address step one for businesses 100 to 1000 employees. If your business is smaller or larger you may find a nugget or two of value as well.
Challenges of “Mid-Sized Companies”
Mid-Sized business is an interesting market segment because the business is big enough to see substantial value in technology however, too small to be on any big technology brands “focused account” list. Businesses in this category generally buy out-of-the-box applications to solve a majority of their business needs. In some cases a company will have a heavily modified ERP or CRM. In even fewer cases the company will have a self developed proprietary software which drives competitive advantage.
Technology staffing is particularly hard. Your company needs the top talent but you struggle to recruit and keep them. The constant turnover in the IT department has led to partial project completion, a sprawl of technology, and a hodgepodge of hardware and vendors – all of which is undocumented. The IT staff you have retained are most likely B and C players leading to general unhappiness of IT from other employees. This cascades into retention issues in other departments. An article in TechGirl warn employers by saying, “Employees are constantly evaluating the whole experience of what it’s like to work for your company – IT included.” 4

There are key advantages of Mid-Sized businesses which will accelerate any digital transformation. First, the executive staff is deep in the weeds of the business. What I mean is, the CEO or COO is likely on the plant floor talking to employees about what is working and not working. Second, the business strategy is well known by all employees. Mid-sized companies can’t afford employees which have not bought into the mission. Employees create a very personal connection to the business in mid-size firms. Third but certainly not least, the cost of change is low and the measurability of change is high. If a technology decision can save one million dollars over 3 years it will make a huge impact to a mid-size company. Imagine the impact of that same million dollars in a billion dollar revenue company. The billion dollar company executives may see the entire project as too costly due to having diverted people off more lucrative projects.
Where to Start
You are probably assuming I am going to say step one is a business or technology assessment. You are only partially right. The truth is, you most likely need a very detailed assessment. A mid-sized company needs the A-team to spend quality time with the business to unscramble the years of technology debt and create a technology strategy which aligns to the business strategy.
The problem is, it’s expensive. It’s expensive from a pure dollars perspective but also from a time investment perspective. Someone – mostly the C Suite – is going to have to teach the consultants enough about the business, the challenges, and the opportunity for them to provide any reasonable recommendations. Assessments are even more challenging when the consulting firm sells and implements its recommendations. Should a company get two assessments? Three? Now things are getting out of hand. Employees wonder why the CEO goes off to a conference, meets other CEO’s, and comes back with three IT initiatives. It’s difficult to get no-biased recommendations.
I’m not anti-
What is the solution?

Start with a single sign-on solution (SSO). Why? Think of SSO as the keys to the kingdom when every door has a different lock. Capterra has a good article titled, “Single Sign-On: What It Is, How It Works, and Why You Need It” which gets into the nuts and bolts a bit more than this article if you are interested. SSO can also be the pebble which starts the landslide of discovery and change.
I’ll explain. When a medium-sized business embarks on an SSO project there is a clear goal; all software and services must integrate with the single sign-on service. At first, this may seem like a trivial exercise. It’s not. What you will soon discover is some or none of your software supports SSO. Don’t panic, this is the pain associated with change and the reason I recommend to start with SSO. The good news is you will be able to take a victory lap on the numerous small wins associated with the project.
Before you embark on the SSO journey you will have to decide what you want to use for identity source. There are many options including cloud identity services, one of your own applications (HR systems), and Active Directory to name a few. When you are looking at SSO solutions you should ask what is used or available for Identity and Access Management (IAM).
As you can see the SSO project is already illuminating sections along the digital transformation path. You have inadvertently started an application assessment and decided on a source of truth for your users’ Identity.
I recommend starting with your line of business application(LOB). The LOB application houses some of your most sensitive data and is critical to the day to day operation of the business. If your LOB app does not support SSO you may want to pause this project and consider if the LOB is the right fit going forward. If the line-of-business application doesn’t support SSO, it may support external authentication. External authentication should never be confused with SSO. SSO mixes the single authentication source with the ability to seamlessly log into all integrated application. Hence, reducing phishing, browser hacks, and other very common security concerns. External authentication will at least get you part of the way there while you are waiting for a feature to added for SSO or
Assuming your line of business application is compatible with single sign-on, you will discover during configuration, there are accounts on the system which are old, wrong, or unknown. This is bad and normal. After all, this LOB application has probably been around a while through various IT personnel and software integrations.
During the configuration of the line of business application you have just done a miniature user audit. You took the time to look at who has access to what in order to configure the correct rights for their SSO user. Every other user you have disabled or deleted.
Now is the time for that first victory lap I promised you. Because of the SSO project we have:

- We have assessed the viability of SSO of our LOB app.
- Chosen our identity provider (aka single point of truth for users and passwords)
- Performed a user audit and clean up of accounts on the LOB app.
- Ensured the right users have the right privileges on the LOB app.
- Provided an authentication method which will function on any device
The same steps we followed for the LOB apps are the same steps we follow for all the applications in the company. The result is a complete assessment of the companies software and its ability to use a single sign-on provider, the software users, and all user access. I would argue single sign-on is a basic litmus test for modern software and a basic characteristic you should use in your evaluation process.
The great news is all this hard work “assessing” your software is directly attributable to completing
Win Win for all Stakeholders
There is rarely a solution which benefits all stakeholders in such a tangible and meaningful way as single
Executives Alignment
The business strategy is filled with staffing, real estate, marketing, sales targets, acquisitions, etc. Single sign-on increases the operational tempo of the business allowing for the faster and cheaper completion of the strategy. When the “how” is less complicated the “what” happens much faster. Many of the things the Executive team wants to accomplish will require social and process transformation technology transformation
Technologist Alignment
Contrary to what users may think, it is not a technologists dream to be the maestro of user accounts and access on 50 different software platforms. It is not fun for them to say, “I’ll have to ask” when users ask for access to a software application that Bob or Carol have access to even though everyone does the same job. T
User alignment
As stated in the opening of this article, the user community is changing. Every interaction with the company is tested and weighed against the alternatives at other companies. You may have witness an example of one employee moving to another company and soon after other follow. It’s a simple cause and effect. The user who moved first simply communicated the benefits of the new company. With the advent of social media your user experience is tested against others easily and frequently.
Single sign-on elevates the user experience in mid-sized companies significantly. Employees can get the access they need based on their role and not who set up their access and in what year. SSO opens the door for alternate work styles and better work-life balance. Remember the days when a manager used to lock up the office after the last person left? Don’t remember them fondly, those are dark days. Remember when someone wanted to work from home IT had to go to their house and set up their computer, connect an VPN or sent them home with the travel laptop? Very dark days.
Step one of many steps

The digital transformation journey is a long one. Technology could be disrupted again and again during this journey. Starting with SSO will lead to greater transformation opportunities. An organization which embraces transformation will have a greater chance of negotiating change and accomplishing strategic objectives.
Remember the definition of Digital Transformation at the beginning of the article, “transformation of business and organizational activities, processes, competencies
Recommendation
There are many solutions on the market for SSO. As a Cloud Solution Strategist at VMware, I am most knowledgable and therefore partial to Workspace one.
To reiterate, SSO
Message to Service Providers

VMware has a tremendous MSP program for providers to add value and help end customers. The mid-market is a key market for service providers because they are big enough to invest in their business while small enough to need help. Workspace One is a multi-cloud solution which requires no previous VMware experience.
Thanks for taking the time to read. Comments open below.
Greg
- https://www.bizjournals.com/bizjournals/on-numbers/scott-thomas/2012/07/2-percent-of-all-companies-are.html
- https://www.sba.gov/document/support–table-size-standards
- https://www.forbes.com/sites/groupthink/2012/08/29/how-big-is-a-small-business-heres-why-it-matters/#1c6998235c5d
- https://www.pe.com/2015/03/14/tech-girl-how-technology-impacts-employee-retention