Everything Teams Ask Before Choosing Digital Asset Management

A candid conversation between Ben Jata and the founders of Stockpress - Jessica Storry (CEO) and Ian Parkes (CRO) - about what Digital Asset Management actually solves, where teams struggle, and how to know when it’s time to move beyond shared drives.

There’s a point most growing teams eventually hit. Someone can’t find the latest logo. A designer recreates something that already exists. Marketing launches a campaign with outdated assets. A freelancer asks for access to files… and nobody knows which folder to send.

At first, it feels small. Then one day everyone suddenly realizes: “We have the content. We just can’t find it anymore.” That’s usually the moment teams start looking into Digital Asset Management (DAM).

But if you’ve ever searched for DAM software online, you’ve probably seen a lot of:

• Feature lists
• Enterprise jargon
• Governance diagrams
• Complicated workflows
• Comparison tables that somehow make every tool sound identical

It’s something I first experienced in my role as Global Vice President at Authentic Brands Group, and have continued to see across multiple teams and industries through my new operator-led advisory firm, RDigital.

With the subject seemingly felt across teams of all sizes and functions, I wanted to dive into it deeper. Having known Jessica and Ian for a few years, we thought it would be useful to approach it through an interview-style Q&A, where I could ask the questions I hear from the operator side about this often misunderstood category.

The interview took place in June 2026, with the mission being to candidly talk to Jessica and Ian about the questions teams should actually ask before choosing a DAM. Not just: “What does DAM do?” But:

• Why do teams struggle to find files?
• When do folders stop working?
• What actually breaks first?
• Why do some DAM projects fail?
• What should modern DAM feel like today?

Here’s the conversation. Enjoy!

Part 1: Why Teams Start Looking For DAM

Ben: What usually breaks first before a team starts looking for DAM?

Ian: Honestly? Usually not storage. Most teams already have places to put files. Dropbox. Google Drive. Shared folders. Slack threads. Email attachments. Random hard drives. Somebody’s desktop.

The first thing that really breaks is confidence. People stop feeling confident they can find the right thing quickly.

That’s when you start seeing:

• Duplicated work
• Outdated assets being reused
• Teams asking the same questions repeatedly
• Creative bottlenecks
• “Can someone send me the latest version?” messages all day long

And the interesting thing is most teams don’t notice it happening gradually. It kind of sneaks up on them.

One day they suddenly realize: “It’s easier to recreate this than find it.” That’s usually the real tipping point.

Jessica: I think another thing that breaks is visibility. When teams are small, people can usually rely on memory. You know where things live because you were involved in creating them. But as more campaigns, channels, contributors, and stakeholders get added, that shared memory disappears.

Now someone in marketing needs an approved asset. A freelancer needs access. The social team needs resized versions. The web team needs updated campaign visuals.

And suddenly content exists everywhere. The issue usually isn’t that teams are disorganized. It’s that the systems they started with were never really designed for growing collaboration.

Ben: Why do shared drives and folders stop scaling for growing teams?

Ian: Folders work surprisingly well… until they don’t. And honestly, that’s why so many teams stay with them longer than they probably should.

The challenge is that folders rely heavily on people already knowing:

• Where something lives
• What it’s called
• Who uploaded it
• Whether it’s approved
• Which version matters

That’s manageable when you have:

• A handful of users
• Limited campaigns
• Low content volume

But modern marketing and creative teams produce huge amounts of content now.

Photos. Videos. Social assets. Brand files. Campaign variations. Localized versions. Short-form video. Product imagery. Internal decks. External partner content. At some point the folder structure becomes less of a system… and more of an archaeological dig.

Jessica: The other issue is that folders don’t really understand relationships between content. A campaign isn’t just one file.

It’s usually:

• Multiple versions
• Multiple formats
• Multiple channels
• Approvals
• Comments
• Updates
• Collaborators

Folders don’t give teams shared context. They just give them places to store things.

Modern teams usually need more than storage. They need:

• Discoverability
• Visibility
• Organization
• Collaboration
• Confidence

That’s a very different problem.

Ben: Why do creative and marketing teams waste so much time finding files?

Ian: Because most systems still expect humans to do all the remembering. That’s the core issue. People remember differently.

One person searches by campaign. Another searches by product. Another searches by region. Another remembers who designed it. Another remembers what color it was.

Folders are rigid. Humans aren’t. That mismatch creates a huge amount of friction.

Jessica: And often teams are actually doing the right things. They’re naming folders carefully. They’re organizing things logically. They’re trying to create structure. But the amount of content modern teams create has exploded. Eventually manual organization alone becomes difficult to maintain.

That’s where things like metadata, tagging, AI-assisted organization, search, and visual browsing become really important. Because now the system can help people find things in the way they naturally think.

Part 2: What DAM Actually Solves

Ben: What is DAM actually for?

Ian: At its simplest, DAM helps teams find, organize, share, and reuse content without wasting time. That’s really the core of it. There’s obviously a lot more modern DAM platforms can do today.

But fundamentally, DAM helps teams stop losing momentum because content is scattered.

Jessica: I think people sometimes assume DAM is mostly about storage.

But the real value usually comes from:

• Clarity
• Accessibility
• Collaboration
• Consistency

The best DAM systems help people feel confident they’re working with the right content. That’s a much bigger deal than it sounds.

Especially when:

• Multiple teams are involved
• External collaborators exist
• Campaigns move quickly
• Brand consistency matters

Ben: Is DAM just cloud storage?

Ian: No, although that’s a very common misconception.

Cloud storage answers: “Where can we put files?”

DAM answers: “How do teams actually work with content together?”

That’s a very different question. Cloud storage is usually passive. DAM is operational.

Jessica: That’s why things like search, approvals, metadata, version control, portals, sharing permissions, tagging, collections, and collaboration matter so much. Because modern teams aren’t just storing content.

They’re constantly reusing it, updating it, distributing it, collaborating around it, and adapting it across channels.

The workflow matters.

Ben: What’s the difference between DAM and file management?

Ian: File management is usually about storage structure, folders, permissions, and moving files around.

DAM is more about discoverability, collaboration, operational workflows, content reuse, brand consistency, and speed.

The easiest way I usually explain it is: file management helps teams store content. DAM helps teams actually use content.

Jessica: And importantly, DAM helps teams scale content operations without scaling confusion. That’s a huge part of it. A lot of teams today are producing more content than ever before.

But if people can’t find it, trust it, reuse it, or share it, then the value of creating it drops really quickly.

Part 3: Who Benefits Most From DAM?

Ben: What kinds of teams benefit most from DAM?

Ian: Usually teams where:

• Content volume is growing
• Collaboration is increasing
• External sharing exists
• Approvals matter
• Finding files is becoming harder

That can be:

• Marketing teams
• Creative teams
• Content teams
• Ecommerce brands
• Nonprofits
• Manufacturers
• Agencies
• Education teams
• Media organizations

It’s less about company size. And more about: “How operationally complex has content become?”

Jessica: I also think teams benefit most when they genuinely want adoption. That sounds obvious, but it matters. Some systems are incredibly powerful, but difficult for everyday teams to actually enjoy using. We’ve always believed usability matters. Because a DAM nobody wants to use doesn’t really solve anything.

Ben: When is DAM probably overkill?

Ian: Honestly? Sometimes shared drives are completely fine. And I think more DAM companies should say that.

If you have a very small team, low content volume, limited collaboration, and simple workflows, then folders may genuinely work well for you.

DAM becomes much more valuable when content scales, teams scale, channels scale, contributors scale, and complexity scales.

That’s usually the moment things start breaking.

Jessica: And I think teams should feel empowered to ask: “Are we solving a real problem?”

Not: “Should we have DAM because everyone else does?”

The best DAM implementations usually happen when teams clearly understand what’s slowing them down, where confusion exists, and what operational friction they’re trying to reduce.

Ben: Why do external collaborators create so much complexity?

Ian: Because the second content leaves your immediate internal team, visibility becomes harder.

Now you have agencies, freelancers, distributors, partners, franchisees, photographers, videographers, and regional teams all needing access, uploads, approvals, downloads, and brand consistency.

That’s where things can get messy quickly.

Jessica: And usually people try to solve this manually.

Which creates:

• Endless shared links
• Duplicated folders
• Outdated downloads
• Permission confusion
• Broken workflows

A modern DAM should make external collaboration feel simple. Not like everyone’s tiptoeing around infrastructure.

Part 4: Why DAM Projects Fail

Ben: Why do some DAM projects struggle with adoption?

Ian: Because a lot of DAM projects historically focused more on governance than usability. And governance obviously matters.

But if the system feels complicated, slow, admin-heavy, difficult to search, and difficult to upload to, people stop using it. And when people stop using it, content quality inside the system starts declining too. It becomes a cycle.

Jessica: I think another big issue is expecting teams to completely change how they naturally work. Good product experiences usually meet people where they already are.

The more friction there is during onboarding, during upload, during sharing, and during search, the harder adoption becomes.

That’s why we care so much about onboarding, simplicity, visual UX, search experience, and reducing admin work. Because those things directly affect whether teams actually use the platform consistently.

Ben: What makes onboarding successful?

Ian: Momentum. The best onboarding experiences help teams get value quickly.

Usually that means:

• Uploading content
• Organizing it
• Inviting people
• Sharing something useful

Once teams experience, “Oh… this is actually easier,” adoption becomes much more natural.

Jessica: And the experience has to feel approachable. A lot of teams looking at DAM aren’t DAM experts. They’re marketers. Designers. Content creators. Brand teams. Operations people. The software should support them. Not make them feel like they need a certification before getting started.

Part 5: What Modern DAM Looks Like Today

Ben: How has AI changed DAM?

Ian: Massively. Especially around organization and findability. Historically, DAM systems relied heavily on manual tagging.

Now AI can help:

• Identify content
• Generate tags
• Transcribe video
• Extract text
• Improve searchability
• Reduce admin work

That’s incredibly valuable for teams managing large content libraries.

Jessica: The important thing is that AI should feel supportive. Not overwhelming. The best AI experiences usually reduce friction quietly.

They help teams organize faster, find content faster, upload faster, and work faster without turning the product into a science project.

Ben: What should teams prioritize first when implementing DAM?

Ian: Not perfection. That’s probably the biggest thing.

A lot of teams think they need perfect taxonomy, perfect metadata, perfect folder structures, and perfect governance before they can start.

Usually it’s better to focus on momentum, adoption, core workflows, getting content centralized, and helping teams experience value quickly.

You can evolve structure over time.

Jessica: And focus on real workflows. Not theoretical workflows.

Questions like:

• How do people actually search?
• What do teams struggle to find?
• Who needs access most often?
• Where does collaboration break down?

Those questions usually matter more than creating the perfect organizational diagram.

Part 6: When Teams Outgrow Dropbox And Google Drive

Ben: What are signs a team has outgrown Dropbox or Google Drive?

Ian: Usually one or more of these starts happening:

• Nobody knows which version is approved
• Content gets duplicated constantly
• Teams rely heavily on Slack messages to find things
• Folders become extremely deep
• External sharing becomes chaotic
• People recreate existing work
• Campaign assets become difficult to locate
• Onboarding new team members takes too long

That’s generally the moment teams start realizing: “We don’t really have a storage problem. We have a content operations problem.”

Jessica: And often people feel the friction emotionally before they can fully explain it operationally.

Things start feeling slower, messier, harder to trust, and harder to navigate. That’s usually a sign the current system isn’t scaling with the team anymore.

Ben: What does a healthy migration from shared drives to DAM look like?

Ian: Gradual. Not: “Stop everything and rebuild the universe.”

The healthiest migrations usually focus on current campaigns, active assets, important brand content, and high-value workflows first.

Then expand from there.

Jessica: And communication matters a lot.

People need to understand why the change is happening, how it helps them, and what becomes easier.

The best onboarding experiences feel supportive. Not forced.

Ben: Final question — what do you think teams really want from DAM today?

Ian: I think most teams want something that simply helps work move faster. Less friction. Less searching. Less duplication. Less confusion. More clarity. More collaboration. More confidence. That’s really the heart of it.

Jessica: And honestly, I think people want software that feels human. Something approachable. Something supportive. Something that works with teams instead of making them adapt to it. Because content operations affect people every single day. When those workflows feel easier, work feels better too.

Final Thoughts

Digital Asset Management has changed a lot. It’s no longer just about storing files.

Modern DAM is increasingly about:

• Helping teams collaborate
• Reducing operational friction
• Improving findability
• Scaling content workflows
• Supporting growing teams
• Helping people work with more confidence

And for many teams, the biggest shift isn’t: “Should we get DAM?”

It’s: “When did folders stop being enough?”

If that question feels familiar, it might be time to take a closer look.

Want To See What Modern DAM Looks Like?

Explore how Stockpress helps marketing, creative, and content teams organize, find, and share content without the complexity of traditional enterprise DAM.

Related Resources

• DAM vs file management
• Moving from Dropbox to DAM
• DAM for marketing teams
• DAM for creative collaboration
• Affordable DAM software 2026
• Why teams struggle to find files

Stockpress: What is Digital Asset Management?

About Jessica, Ian And Stockpress

Jessica Storry, Ian Parkes, Bart Romanowski, and Kamila Romanowska are the co-founders of Stockpress. Before launching the company, they ran a digital agency together, building websites, apps, and digital experiences for startups and enterprise organizations. Across both client work and their own internal workflows, they repeatedly saw the same challenge: teams were creating more content than ever, but files were often difficult to organize, find, and manage effectively.

That experience led them to build Stockpress.

Stockpress is a modern, affordable Digital Asset Management (DAM) platform built for marketing, creative, content, and brand teams that have outgrown basic file storage tools like Dropbox and Google Drive, but don’t want the cost, complexity, or heavy lift of traditional enterprise DAM platforms. Designed to bridge that gap, Stockpress makes it easier to organize, find, share, and manage digital assets in one place - combining powerful functionality with a simple, self-serve experience that teams can adopt quickly.

Today, the team continues to shape Stockpress around a clear belief: managing content shouldn’t take longer than creating it. Their focus remains on helping teams bring more structure, visibility, and control to the way digital assets move across marketing, creative, and content workflows.

About Ben Jata

Ben Jata is a growth operator and ecommerce executive with 15 years of experience helping brands scale across digital, retail, and marketplace environments. Over the course of his career, he has worked across growth, performance, ecommerce, and operational excellence - giving him a practical view of how modern brands actually build, sell, and adapt.

Today, Ben is focused on his work with RDigital, where his attention is increasingly centered on the intersection of growth, operational efficiency, AI, and how brands can evolve in a fast-changing digital landscape. His thinking often explores a bigger question: how companies build stronger foundations before layering on technology, automation, and scale. With a sharp operator mindset and a strong understanding of ecommerce and digital transformation, Ben brings a practical, no-fluff perspective to conversations around growth, systems, and what it really takes to build modern businesses well.

This interview is shaped by that lens - looking beyond trends and into the real operational, strategic, and growth decisions that move businesses forward.