Dmitry Shamis — HubSpot’s Global Head of Creative & Brand — is, unsurprisingly, a smart guy. In particular, he’s a shining leadership talent. Why else would someone who’s never held a traditional “creative” role be leading a 155-person strong creative organization?

How did Dmitry land this role? He started in the talent agency world, before switching to programming, before joining HubSpot back in 2015. At the legendary software company, he rose up the web development ranks, eventually becoming the Director of Web Development before taking his empathetic leadership style to the company’s creative team.

Dmitry — one of Air’s operator-investors — spent some time with us to share how he and his team approach Creative Ops, and why he thinks dedicated Creative Ops hires are necessary, and more.

How do you define Creative Operations?

Creative operations is the enablement of creative work. It’s the tools, systems, processes, and relationships that allow for creatives — makers — to actually do their job.

Is Creative Ops your job as the Head of Creative, or do you have dedicated people doing that work?

We are fortunate to have a creative team with multiple focuses. To support that, our team is divided into three pillars: Creative Studio, Web Development, and Creative Operations. Creative Operations is essential to our greater team's success.

That's where we have project management, production, and resource management. That’s also where we have our “creative solutions” program, which is a self-service and enablement function for our marketers.

At the end of the day, if we think about all of the work that comes in, and all the people we have, we don't have enough resources. Look, my team is huge. But so is our workload! I think that’s everyone's dilemma, at any company — but the reality is this: not all of the work assigned to our creatives should be done by them; some tasks are better accomplished through outsourcing or self-service to protect creatives’ time

Creative Operations, as a function, creates space and capacity for our creatives to focus on the highest impact, most forward-thinking work.

What’s the ratio of creatives to Creative Operations people on your team? Is there a “magic” ratio?

I don't know what a magic ratio might be. We're probably about two to one in terms of creatives to ops. But even then that’s not illustrative of all of the work — there are plenty of folks on Creative Ops who aren’t focused on the day-to-day projects. They’re focused on their own enablement work.

So if we think about who's doing the work, and who's enabling the work, it’s probably more like three to one or even four to one. And I think that's okay because you don’t want to overwhelm your project managers and your producers with too much to manage. You want to make sure that they feel challenged and feel empowered to do the best work they can and you’ve got to strike that balance. But I think any any given project will likely have three to four people plus some stakeholders, and I think that's probably a relatively good balance.

What do you think are like the necessary skills or traits to be like an effective Head of Creative, or any other creative leadership position?

To be an effective leader, period, you have to listen, be empathetic, and remove obstacles from your team's path. You have to help them grow and provide them with the resources they need. When it comes to creativity, an added level of trust is required. As I'm not a designer, video editor, animator, project manager, UX designer, UX researcher, or producer, I have to trust that the people I work with will ensure the best results.

A good leader should have opinions, but those opinions shouldn't prevent the work from being the best that it can be. I feel comfortable pushing back on a designer and asking questions; I feel comfortable pushing back on a producer and asking questions; but at the end of the day, I trust that when they push back on my pushback, it's coming from a place of experience, research, and knowledge.

What are the consistent challenges of Creative Ops, that you’ve seen at every point of scale, as you’ve built out the team?

The biggest challenges are processes. The processes you run for a 30-person team are not the processes that you should be running for a 155-person team. It’s not just who's responsible for moving tickets in Asana — it’s what is the review cycle? When do we demo? When do we do retros? How do we iterate on things? How do we ensure that our planning is solid?

When you're planning 30 people's work, it's a lot of time and effort. When you're planning 155 people's work…I still don't know how it's possible. Creative Ops is crucial to ensure you move forward are set up to succeed; without it, everyone is scrambling; then your stakeholders are mad because they're putting in requests and they're not hearing back; they don't know what's going on.

Your creatives get mad because feedback is coming in at all times of day, from all different directions. What do we listen to? What do we not? All these things become so unclear. Having a group of people focused solely on building the process out and creating a scalable system for small projects, large projects, and handoffs has been so critical.

In the Creative Operations equation, what are your creatives’ and stakeholders’ biggest pain points?

The creatives will have many opinions about Creative Ops: things aren't moving fast enough; change takes time; transitions take time; work isn’t moving fast enough. It's painful simply because change is difficult to deal with.

On the other hand, they’re happy because they're no longer getting "shoulder taps" — constant requests for updates, like ‘how's it going?’ or ‘can I see a quick peek?' That's better.

They're also not doing as much operational work. If someone's on the clock for 40 hours per week and spending 20 of those hours updating tickets and charts, that means half their time isn't spent doing their actual job. So they're able to focus on what they're here to do.

Stakeholders often find it frustrating when it's not clear who to approach for help. To address this, we have built a world where programs have dedicated project managers. The teams we work with have a single project manager to approach, so there is accountability and clarity in communications.

Stakeholders don’t need to talk to the designer, the dev, or any of our creatives. They talk to the PM. We've trained our creatives to say, ‘thanks for reaching out, but go talk to the PM.’ All roads lead to the PM. We make sure to involve stakeholders in organizational changes and shifts — collect feedback, make sure they feel heard, and give them a seat at the table. That's how we've mitigated some stressors. You can't make everyone happy, though.

That said, I don't think making stakeholders happy is the goal, though. Ultimately, if the creatives can do better work, the business will succeed and then the stakeholders will be happy. They may not see it that way; they may feel like they're losing their "toys". But in reality, they — and the brand, and the bottom line — will benefit more in the long run.

What are the essential tools, as in software, of Creative Operations at HubSpot?

There are many different tools we use. Our primary ones are Asana, Jira, Figma, Frame.io, Canva, and Slack. We have our own web module system that we built. We’re still using a DAM.

So, those are the primary tools. We still have a lot of work to do to fully automate them, but just having things organized and having places to point people for what they need has been really helpful. For example, Canva helps us crank out thousands of design assets a month without requiring a single designer. This is a huge benefit to the business: it saves time for creatives and money for the business, since we don't have to hire external agencies. As a result, we can do a lot of things at scale, which is very helpful.

What I’m hearing from you is that the boiled down goal of Creative Operations is to create automation opportunities and maintain a single source of truth approach. True?

Yeah, absolutely. My team's job is to help build the HubSpot brand and share it. Consistency is arguably the most important aspect of any brand — consistency is what builds trust with your audience.

Ensuring there's a single source of design truth that lives in Canva, that our designers are contributing to and our marketers are then utilizing, is crucial. There's a single source of truth for our web components, that feed into those web modules, that our marketers are then using to, again, ensure consistency and trust.

The automation angle is just a reliable way to speed things up. I dream of a future where we're one click away from launching anything. We’re ready to eliminate many manual processes right now — cloning, moving, exporting. Things that aren't fun, but enable the marketers to actually get work done.

How do you see Creative Operations evolving over the next five years, as a field?

It's a really good question. The next five years, we're going to see Creative Ops continue to serve as a conduit to creative work.

Consider the in-house agency. More and more companies are building them but there are a lot of considerations a business must take in building them, starting with the work itself. There's work that you want your in-house creative team doing; there's work that you don't want your in-house creative doing, either because they don't have the skill set or because it's not a good use their time.

So I think Creative Ops will become more of a conduit to a hybrid in-house and external creative agency approach. It’s going to be a split between in-house resources, focused on brand and focused on big swings, and external resources focused on the drum-beat work, the evergreen work — still incredibly important and impactful to the business, but it doesn't need to be done in house.

The way I think about it, and how I position external agency hires to my team is I want my people figuring out playbooks, writing new playbooks for new work, and then handing those off. A good Creative Ops function optimizes those handoffs to set our external partners, and ultimately our business, up for success.