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Mike Lieberman, CEO and Chief Revenue ScientistThu, Jul 15, 2021 17 min read

Rate Your Digital Transformation Progress: Are You Ahead, Behind Or On Track For Success?

Answer These 9 Questions To Measure Your Progress Against Other Companies Like Yours

In case you’ve been under a rock for the past 18 months, companies have been aggressively transforming how they go to market, and specifically how they apply digital technology to marketing, sales and the customer service areas of their businesses.

This is commonly referred to as digital transformation, and it’s exploding. To be clear on exactly what digital transformation is and what it isn’t, I share this definition from The Enterprisers Project:

“Digital transformation is the integration of digital technology into all areas of a business, fundamentally changing how you operate and deliver value to customers. It’s also a cultural change that requires organizations to continually challenge the status quo, experiment and get comfortable with failure.” For more on this, consider clicking on this link.

But over the past six months or so, we’ve seen a trend in companies thinking they’re already doing this when, in most cases, they’re not even close to understanding the scale and scope of what digital transformation actually entails.

So for your educational enjoyment, we’ve created nine questions that, depending on your answers, will uncover whether you’re tracking to be ahead, behind or on pace for keeping up with what innovative and progressive companies are already working on for digital transformation.

1. Is Your Entire Company And Leadership Team Aligned And Bought Into A Long-Term Digital Transformation Initiative?

If you can answer yes, you’re ahead of the game. This is a big lift for many organizations, and most underestimate the importance of alignment across the organization.

If you’re unsure of your answer, then you’re not aligned and you need to get aligned quickly. Since this initiative impacts every single part of the company, you can’t afford to have a single team or department not on board with this approach to the business.

If you answer no, then our advice is to hit the pause button on anything you’re working on in this area and do a major reset. It’s not possible to transform anything across your organization without 100% alignment and buy-in from the entire organization.

From the very newest sales rep all the way up to the CEO, everyone must understand the importance of the initiative as it relates to your survival as a business. It’s equally important to your ability to differentiate your business and grow. Without this approach, growth will be exponentially harder.

Once everyone is aligned, the rest of the tasks will be much easier to execute.

2. Do You Have The Resources (Internal Or External) To Help Guide You Through The Transformation?

If you can answer yes to this question, you’re ahead of the curve. Again, most organizations lack the expertise to pull off a massive cultural and corporate change initiative like this.

If you’re not sure or outright don’t think you have the right resources, you’re not alone. Almost every organization lacks the right resources internally, and the smart ones have brought this expertise in from the outside.

This might take the form of an outside consultant (or two or three consultants). These people have led digital transformation initiatives for other companies like yours – many other companies, preferably.

If you prefer a company to a single person, then consider bringing in an agency that has the experience helping organizations like yours transform marketing, sales and customer service execution.

The strength of a company or agency is that they offer a wider variety of expertise and skills. If this is what they do, they can look at the overall strategy, timelines, investment requirements and resources required.

Then they transition into the tactics, including sales process, sales tools, marketing tools, marketing tactics, customer service tools and the analytics to track the entire customer journey. They can also bring in the technology partners required to properly automate, report on and help optimize this “click-to-close” execution over time.

3. Do You Have A Documented Sales Process?

The questions might get easier from this point on. To answer yes to this, you have to be able to present a printed visual representation of your current sales process. Everyone in sales has to have a copy of your sales process and they have to be working their hardest to follow it.

You and your leadership team have to be referring to it and encouraging everyone to follow it. There can be no alternative sales processes, no matter the scenario.

If you don’t meet the definition above, or if you can produce a document but your sales reps aren’t following it religiously, then you don’t have a documented sales process.

While this is more common than you might imagine, it’s dramatically impacting your ability to keep up with your competition, and without it there is no way to productively digitally transform your sales process.

Digital Transformation at Mid-Sized Companies4. Are Your Sales And Marketing Teams Aligned?

A lot of people think their marketing and sales teams are aligned, but for true alignment here are the criteria you should be looking for.

They have shared goals around revenue. This means both teams, or any individuals, achieve success both financially and publicly when the company hits its revenue goals.

They meet together and talk about the quality of leads, the number of leads and the follow-up associated with leads generated. Everyone on both teams is intimate with the conversion metrics associated with each stage of your revenue cycle.

It might mean that you have a service-level agreement (SLA) between both teams, although that is not a requirement. It means whoever is leading marketing and whoever is leading sales works together on all aspects of both marketing and sales execution.

It might mean you have a single executive or chief revenue officer (CRO) leading both marketing and sales. But again, that is a nice to have, not a need to have.

If you look across your organization and you don’t see any of this, then you’re not leading the pack, you’re falling behind.

5. Have You Mapped Your Prospects’ (And Customers’) Buyer Journeys?

Again, to answer yes to this question, you need to have a visual representation of your entire prospect and customer buying journey. What are the steps in that process? Who is taking those steps? What questions are they asking? What concerns do they have? How do those questions and concerns change as they move from stage to stage in that journey?

What are all your touch points, and how do those touch points make your prospects and customers feel? How have you designed your marketing, sales and customer service processes to create remarkable experiences at every touch point? We call those little WOWs, while other people call them peaks.

Those little experiences create memories for your customers. These help them become advocates and tell compelling stories about your brand. They are critical to driving scalable growth.

There is no middle ground here. Either you have this map and you’ve done the hard work to map your entire prospect/customer journey, or you haven’t. There is no half-done here. You either did it completely and you’re using it to improve the experience, or you still need to do it.

6. Do You Have A Marketing, Sales And Service Technology Platform?

I said the questions would get easier. Most people know whether they have the technology to drive true digital transformation or not.

Are you using a marketing automation platform like HubSpot, Adobe, Pardot, SharpSpring or Zoho? Are you using a CRM like HubSpot, Salesforce or Pipedrive?

What are you using for customer service? Zendesk, Freshdesk or HubSpot?

It doesn’t matter what you use, but you have to use something. The more integrated and connected the tools, the easier it’s going to be to drive the transformational gains you’re looking for.

If you can answer yes to all three areas of the business, you are ahead of about 50% of the people you’re competing with.

If you can only answer yes to one or two of the areas, you’re probably not ahead at all but simply on par with the others.

If you are not using anything in all three areas, you’re behind for sure, and you need to quickly consider looking into marketing, sales and customer service software to improve your prospect and customer experience.

Technology Platforms for Digital Transformation7. Have You Created Content To Engage Prospects And Customers?

This is the trick question on the list. You might think you have engaging content, and you probably have content you’ve been using for both marketing and sales, but let’s be clear here – this isn’t that.

This is not product information. It’s not company information. It’s not blog articles.

To answer yes, you’ve taken every question ever asked by a prospect during your sales process and created content to answer that question.

You’ve tailored your content to individual roles. If you sell to the COO, CRO and CFO, you would have three different pieces of the same content to target specific role-based biases.

You’ve created industry-specific versions of this content. You have videos of customers talking about how great your company is and how much they’ve enjoyed their experience with you.

You have documented case studies and success stories that can be publicly shared with anyone. You’ve reviewed all of your content and know that every piece is written about your prospect, not about you.

In most cases, people have to answer no to this question. While they might aspire to have this level of content for marketing and sales, they are still working toward this specific capability.

Now for the good news – most of your competition doesn’t have this yet either. But this only means you have a limited window to get your content machine activated, start creating this level of content and then scale it accordingly.

8. Does Your Website Drive A Consistent Level Of Leads For Your Business?

You should know this or at least be able to quickly visit a dashboard to see how many leads your website and marketing are delivering each month.

That makes this a two-part question. Part one: Are you getting leads from your website? Part two: Is it a consistent level?

The question is not about whether it’s enough leads, because almost no one ever has enough leads. But are you getting leads from your website month over month at a similar level?

You can answer yes if you’ve received the same number of leads (plus or minus 5%) over the past six months.

If you haven’t, then you should answer no, and you should know that this puts you behind most companies.

While most companies aren’t satisfied with the number of leads they get, 90% of companies that talk with Square 2 all have some level of lead generation coming from their website. Again, it might not be increasing, but they have a site that does produce leads month over month.

If you do answer no, this should be a signal that you need to immediately make changes in the way you do marketing. Falling any further behind in this area could be significant to the long-term viability of your business.

9. Have You Aligned Investment, Timing And Expected Results Across The Organization?

I saved this question until the end, but it probably should have been one of the first ones you consider.

To answer yes, you need to have run a number of quantitative models that predict data-driven performance metrics for the company across marketing, sales and customer service.

You’ve signed off on the expected results and people with experience creating revenue generation strategies. Plans have aligned the investment required to create, install and optimize those plans with your expected results.

Part of those expected results is the timing of the results. How long is it going to take to ramp up this digital approach to revenue generation? You now know what to expect, including the investment and how long it’s going to take.

If you can answer yes to this question, consider yourself to be in the top 10% and well on your way to creating a company that can scale revenue on-demand.

But if you’re not, this should be one of the first steps you take to get started on the path toward digital transformation and scalable revenue growth.

Now that you know what you should be working on to drive digital transformation and revenue growth for the organization, let’s see how you did:

  • If you answered yes to eight or nine questions, you’re ahead of the curve and likely ahead of your competition.
  • If you answered yes to between four and seven questions, you’re probably on par with most companies in your industry.
  • If you answered yes to three or fewer questions, you’re falling behind quickly.

If you’re in either the on par or falling behind category, you must act now to start moving your company forward.

What worked two years ago won’t work next year. Your prospects are getting smarter. They don’t want cold calls or cold emails. They’re not traveling to big trade shows; in fact, they might not be traveling at all. They’re not going back to their offices, so you won’t be able to stop by and say hi.

You’re going to need to rethink your entire revenue-related execution and do so quickly. Once the companies ahead of you start rolling out their new transformative processes, customers will flock to those brands and those businesses, making it almost impossible for you to catch up.

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Mike Lieberman, CEO and Chief Revenue Scientist

Mike is the CEO and Chief Revenue Scientist at Square 2. He is passionate about helping people turn their ordinary businesses into businesses people talk about. For more than 25 years, Mike has been working hand-in-hand with CEOs and marketing and sales executives to help them create strategic revenue growth plans, compelling marketing strategies and remarkable sales processes that shorten the sales cycle and increase close rates.