Digital Drag is Real — Here’s What Businesses Told Us (And What We Heard)

Video call with business leader and strategist reviewing notes on digital strategy

Digital Drag is Real — Here’s What Businesses Told Us (And What We Heard)

From AI-powered startups to service-led scaleups, here’s what business leaders are really struggling with — and why our DMA conversations feel more like mini-discoveries.

Montage of diverse business owners

Cold Calls That Sparked Real Conversations on Digital Maturity

Yes — we cold-called. And we’re glad we did.

 

In the last quarter, our outreach led to dozens of conversations with time-poor business leaders. Business leaders, marketers, ops leads. Some scaling, some stalling. But all curious.
 

These weren’t just sales calls. They became real conversations.

 

And what they shared has reshaped how we position the DMA — not just as a service, but as a discovery-led clarity tool.

How Our Discovery Framework Works

 

Our call structure isn’t accidental. It’s designed to feel like a conversation, not a pitch. It reveals friction without forcing vulnerability.

We open with your Snapshot Quiz answers. Then we explore five layers:
 
  1. Workflow friction
  2. Visibility and messaging
  3. AI-readiness and scale blockers
  4. Internal drag vs external expectations
  5. Strategy sequencing
 
By the end, most business leaders say the same thing: “This is the first time I’ve said this out loud.”
 

5 Discovery Themes That Showed Up Again and Again

152

Here are five anonymised stories that reflect what we heard:

 

1. The System Integrator with a Vision

Strong technical team, launching an AI tool. But their digital marketing was fragmented — scattered messaging, sporadic updates, and no clear campaign structure. Buyers couldn’t connect the dots between the product’s capability and its value.

 

Dovetail Insight: Their internal capability was impressive, but their outward presence failed to communicate that clearly. By restructuring their messaging cadence and tightening the customer journey, we laid the groundwork for scalable lead generation.

 

Tip: When your tech is complex, your messaging should be simple — clarity builds trust.

 

2. The Healthcare AI Innovator

An AI-enabled health platform with brilliant backend smarts — but zero strategic funnel. Their CRM was rarely used, website messaging was overly technical, and content hadn’t been updated in 18 months.

 

Dovetail Insight: The product was there, but the pathway to adoption was missing. We focused on simplifying buyer-facing language and mapping a conversion-friendly content sequence.

 

Quote: “You’ve got to meet buyers where they are — not where your roadmap is.”

 

3. The Investor-Sensitive Public Company

A national services firm feeling pressure from stakeholders to prove digital traction. Internally, the strategy was robust — but externally, their web presence and investor messaging didn’t tell the same story.

 

Dovetail Insight: We built a 12-month roadmap that aligned internal goals with external communication milestones, creating a consistent narrative for investor updates, board packs, and team rollouts.

 

Tip: Never assume your audience sees what you see — strategy must be visible and story-led.

 

4. The Advisory Firm Bottleneck

Strong brand, consistent referrals — but internal delivery was manual and messy. Their CRM only tracked leads (not clients), and marketing was business leader-led and ad hoc.

 

Dovetail Insight: They didn’t need more leads. They needed automation to reclaim time, and content to support post-sale trust-building.

 

Quote: “Sometimes the fix isn’t more traffic — it’s more time.”

 

5. The Tool-Stacked Startup

They had all the tools — HubSpot, Mailchimp, LinkedIn Ads, Calendly — but little traction. The systems weren’t talking to each other, and nobody owned the strategy.

 

Dovetail Insight: Implementation had outpaced intention. We realigned the tech stack around real buyer journeys, retiring what wasn’t serving them.

 
Tip: Tools help scale clarity — not replace it.

What These Businesses Share: Digital Strategy Misalignment

None of them lacked ambition.

 

None of them needed another tool.

Most had already invested in too many.

 

According to a recent report from Forrester, over 70% of SMBs report under-utilising their tech stack due to lack of internal strategy alignment. Forrester Report
 
They needed:
  • Strategic clarity
  • Better prioritisation
  • Systems that work together, not in isolation

 

As we say in the DMA Webinar:

 
“You’re not underperforming. You’re under-supported.”
 

Watch the Webinar or Start Your Digital maturity Snapshot

Pull-quote graphic or speech bubble from a recent DMA participant

If these themes sound familiar, our new DMA Webinar breaks it all down.

 

No jargon. No pressure. Just insight into what clarity really looks like.

 

Or if you’re ready to find out where you sit, take the Snapshot Quiz and book a Discovery Call.

 

Let’s take a look together.

Share this post with your friends.

Agency Arcade, About Us - Agency Arcade, Contact Us - Agency Arcade, Our Services - Agency Arcade