The Big DAM Interview: What Teams Should Really Know About Digital Asset Management
A candid conversation with Ben Jata, Jessica Storry, and Ian Parkes about why teams outgrow folders, what DAM actually solves, and what modern content operations should look like.
TL;DR: Most teams do not start looking for Digital Asset Management because they run out of storage. They start looking because they lose confidence in their ability to find, trust, share, and reuse content efficiently. In this interview, Ben Jata speaks with Jessica Storry and Ian Parkes about why folders eventually stop scaling, what DAM actually solves, why adoption matters, how AI is changing content organization, and what teams should prioritize when implementing a DAM.
Why teams start looking for DAM in the first place
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 Marketing launches a campaign with outdated assets.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 is usually the moment teams start looking into Digital Asset Management, often shortened to DAM.
But if you have ever searched for DAM software online, you have probably seen a lot of feature lists, enterprise jargon, governance diagrams, complicated workflows, and comparison tables that somehow make every tool sound identical.
It is something I first experienced in my role as Global Vice President of Digital Operations at Authentic Brands Group, and have continued to see across multiple teams and industries through my operator-led advisory firm, RDigital.
Because this subject is felt across teams of all sizes and functions, I wanted to explore it more deeply. Having known Jessica and Ian for a few years, we thought it would be useful to approach the topic through an interview-style Q&A, where I could ask the questions I hear from operators, marketers, and growing teams about this often misunderstood category.
The interview took place in June 2026, with the goal of candidly discussing the questions teams should actually ask before choosing a DAM. Not just “What does DAM do?” but why teams struggle to find files, when folders stop working, what breaks first, why some DAM projects fail, and what modern DAM should feel like today.
Here’s the conversation.
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, and someone’s desktop all become part of the content ecosystem.
The first thing that really breaks is confidence. People stop feeling confident they can find the right thing quickly.
That is when you start seeing duplicated work, outdated assets being reused, teams asking the same questions repeatedly, creative bottlenecks, and “Can someone send me the latest version?” messages all day long.
The interesting thing is that most teams do not notice it happening gradually. It kind of sneaks up on them.
One day they suddenly realize: “It is easier to recreate this than find it.” That is 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.
Suddenly content exists everywhere. The issue usually is not that teams are disorganized. It is 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. That is 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 is called, who uploaded it, whether it is approved, and which version matters.
That is manageable when you have a handful of users, limited campaigns, and 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, and external partner content all start adding up.
At some point, the folder structure becomes less of a system and more of an archaeological dig.
Jessica: The other issue is that folders do not really understand relationships between content. A campaign is not just one file.
It usually includes multiple versions, multiple formats, multiple channels, approvals, comments, updates, and collaborators.
Folders do not 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, and confidence. That is 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 is the core issue.
People remember differently. One person searches by campaign. Another searches by product. Another searches by region. Someone else remembers who designed it. Someone else remembers what color it was.
Folders are rigid. Humans are not. That mismatch creates a huge amount of friction.
Jessica: Often, teams are actually doing the right things. They are naming folders carefully. They are organizing things logically. They are trying to create structure.
But the amount of content modern teams create has exploded. Eventually manual organization alone becomes difficult to maintain.
That is where metadata, tagging, AI-assisted organization, search, and visual browsing become really important. The system can start helping 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 is really the core of it.
There is 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, and consistency.
The best DAM systems help people feel confident they are working with the right content. That is a much bigger deal than it sounds, especially when multiple teams are involved, external collaborators exist, campaigns move quickly, and brand consistency matters.
Ben: Is DAM just cloud storage?
Ian: No, although that is a very common misconception.
Cloud storage answers: “Where can we put files?”
DAM answers: “How do teams actually work with content together?”
That is a very different question. Cloud storage is usually passive. DAM is operational.
Jessica: That is why search, approvals, metadata, version control, portals, sharing permissions, tagging, collections, and collaboration matter so much.
Modern teams are not just storing content. They are constantly reusing it, updating it, distributing it, collaborating around it, and adapting it across channels.
The workflow matters.
Ben: What is 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 this: file management helps teams store content. DAM helps teams actually use content.
Jessica: And importantly, DAM helps teams scale content operations without scaling confusion.
A lot of teams today are producing more content than ever before. But if people cannot 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 benefit most from DAM when content volume is growing, collaboration is increasing, external sharing exists, approvals matter, and finding files is becoming harder.
That can include marketing teams, creative teams, content teams, ecommerce brands, nonprofits, manufacturers, agencies, education teams, and media organizations.
It is less about company size and more about this question: “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 have always believed usability matters. Because a DAM nobody wants to use does not really solve anything.
Ben: When is DAM probably overkill?
Ian: Honestly, sometimes shared drives are completely fine. 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 is usually the moment things start breaking.
Jessica: 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 is slowing them down, where confusion exists, and what operational friction they are 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 may have agencies, freelancers, distributors, partners, franchisees, photographers, videographers, and regional teams all needing access, uploads, approvals, downloads, and brand consistency.
That is where things can get messy quickly.
Jessica: Usually, people try to solve this manually.
That creates endless shared links, duplicated folders, outdated downloads, permission confusion, and broken workflows.
A modern DAM should make external collaboration feel simple. It should not feel like everyone is 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. Governance obviously matters.
But if the system feels complicated, slow, admin-heavy, difficult to search, or 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, upload, sharing, and search, the harder adoption becomes.
That is why we care so much about onboarding, simplicity, visual UX, search experience, and reducing admin work. 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, and sharing something useful.
Once teams experience “Oh, this is actually easier,” adoption becomes much more natural.
Jessica: The experience has to feel approachable.
A lot of teams looking at DAM are not DAM experts. They are marketers, designers, content creators, brand teams, and operations people.
The software should support them. It should 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, and reduce admin work.
That is 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 is 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 is 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?”, and “Where does collaboration break down?” 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 patterns 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 is generally the moment teams start realizing: “We do not really have a storage problem. We have a content operations problem.”
Jessica: 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 is usually a sign the current system is not 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 they expand from there.
Jessica: 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 is really the heart of it.
Jessica: 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.
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 is 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, and helping people work with more confidence.
For many teams, the biggest shift is not: “Should we get DAM?”
It is: “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
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 strategy, 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.
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 platform built for marketing, creative, content, and brand teams that have outgrown basic file storage tools like Dropbox and Google Drive, but do not 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 should not 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.
