Ally Masi is Proving the Power of Micro-Innovation 

Ally Masi’s work spans executive forums, curated peer exchanges, and large-scale activations tied to tentpole events, all focused on creating meaningful, relationship-driven experiences. Rather than relying on traditional formats, Masi prioritizes intentional design, from who’s in the room to how conversations unfold, ensuring every interaction delivers value.

With a background in public relations and a career shaped by both communications and live events, she brings a storyteller’s mindset to experience design. The goal: move beyond logistics and programming to create moments that resonate long after the event ends.

What does innovation mean to you?

To me, innovation is about relentlessly questioning the status quo. I have a real aversion to the phrase 'that's just how we've always done it.' True innovation isn't always big and flashy. A lot of the most meaningful progress my team and I have driven has come from what I call micro-innovations: small, intentional shifts in how we work, how we plan, how we align, that compound into something transformative over time. Whether it's redesigning the way we run Dreamforce's planning cycle or shifting how we drive strategic alignment with our global events teams, those incremental improvements matter just as much, or more, as the bold, flashy headline moments. 

Why is innovation important in events?

The world learned very quickly during the pandemic what event professionals inherently know: the importance of gathering people in a shared space, physical or virtual, and that creating an experience that moves them can’t be replaced. But the way people want to learn, connect, and engage looks completely different from the way it did five years ago and is changing at an exponential pace today. If we're not innovating, we're becoming irrelevant and norms can get stale. The experiences that once were table stakes can stop serving us and our attendees if we don't stay curious and willing to challenge them.

Who inspires you to innovate?

Two of the influential voices I value highly are Priya Parker, whose The Art of Gathering fundamentally shifted how I think about intention and purpose. The idea that a gathering, whether in social or professional settings, only becomes meaningful when the host gets radically clear on why people are coming together in the first place. And Will Guidara's Unreasonable Hospitality, which redefined for me what it means to truly take care of someone. anticipating what people need before they even know they need it, and then delivering it in a way that feels incredibly personal.

But where it all really started was with my mom. She threw the most incredible themed birthday parties, long before Pinterest existed; she'd check out books from the library for ideas. The balloon invitations for my 5th birthday carnival are one of many core memories: we wrote the details on an inflated balloon, then deflated them to send in the mail. Guests had to blow them up to find out the details. The care and creativity she put into everything she did was formative in how I approach my life and career. And now I’m carrying the torch with my own daughters’ over the top and probably never-been-done before themes, like a Squishmallow Winter Olympics ice skating party.

Is it essential to look for innovation outside the industry?

I like to find inspiration from anywhere and everywhere. Some sources are obvious: creative B2C brand experiences, exceptional customer service moments, a beautifully curated dinner or trip that leaves you changed. Others are less obvious. My daughter's first dentist appointment sparked real ideas about how to ease anxiety through experience design. Truly… I even wrote about it. The question I'm always asking is: what did I learn or feel from this experience that I can bring back to work? Once that becomes a habit, you start finding useful ideas in the most unexpected places.

Is being comfortable with failure part of innovating?

It has to be. You cannot push for real change without accepting that some of it won't land perfectly and being okay with that. Which, as any type-A event professional will tell you, is easier said than done.

Last year at Dreamforce, we overhauled one of our core experiences that had, over time, become more about internal org structure than about the customer. Teams were showing up the way they always had out of legacy, and the space had lost its purpose. We got really clear on the job to be done: less about product, more about solutions and hands-on learning. It required new messaging and new ways of working from teams who were used to doing it a certain way. Did it all come together perfectly in year one? No. But it held its own, broke an outdated structure, and now the company's narrative is heading exactly in the direction that experience pointed toward, and we’re ready to build on it this year because of the risks we took last year. 

The other example I always come back to is a virtual event I hosted during the pandemic with the help of Club Ichi leaders Liz Lathan and Nicole Osibodu. A year and a half in, people were getting tired of virtual events, so we knew we had to do something different. We planned a think tank for 200 VP+ leaders with no agenda — we built it live, in real time, so we were talking about what mattered most to the people who showed up - not what mattered most to Salesforce. Risky? 100%. But it was worth it. Attendees told us it was the closest to being in person they had felt since the pandemic started. That taught me that the risk of trying something new is almost always smaller than the risk of standing still.

How do you get buy-in for your innovations?

Data, always, but with nuance. The data alone won't always tell you a clean story. One of the things I'm most proud of recently is a data index model my team built that gave us a normalized way to look at disconnected data points and make a defensible case for how we allocate content and presence across our events. We'd always had the data, but not the framework to tell the story with it. But the data is only part of it. Shifting company priorities don't always show up in the metrics yet, and you have to account for that. When you come in with a clear point of view that's grounded in evidence and connected to leadership signals, it helps drive alignment. Coupling these data-driven instincts with building relationships and trust across stakeholders earns the ability to take bigger risks. 

What's your advice to aspiring innovators?

Start small: micro-innovations are underrated. People think innovation requires a massive budget, a perfect pitch, or a perfect moment. But some of the most lasting changes I've driven started with a small test, a tweak to a planning process, a new way of running an alignment meeting, a playbook that didn't exist before. Those small wins build credibility.

Also, be curious. Notice how you feel as a customer, a guest, a patient, a fan. 

Then be willing to advocate for what you believe in, backed by data, of course, even when it's uncomfortable. Innovation almost always requires you to push against something that's become comfortable.

What innovation are you currently working on?

A lot of what I'm focused on right now is around internal processes and alignment. For the past two years, I’ve partnered with some of my fellow leaders to transform how we come together as an organization to design Dreamforce: getting cross-functional teams from every part of the organization grounded in shared data, aligned on priorities, and working toward the same vision before we ever get into execution. Every year we learn, every year the process improves, and it’s exciting. 

And we're really leaning into how AI transforms the work we’re doing, experimenting with different tools, and taking out some of the time-consuming work so we can elevate where we spend our time and unlock insights that might otherwise have gone unnoticed. AI tools like Claude and Slackbot are incredible partners in helping build strategic frameworks. Instead of starting from scratch, I brain dump the problem I’m looking to solve with whatever resources I can find, call transcripts, decks, survey data, Slack channels and posts, to help me organize and connect the dots. It’s been so powerful already, and there’s so much more to learn. 

What inspires you?

I’m inspired by people who care deeply and show up with intention. Business communities like the ones that I’ve participated in through Skift Meetings and Club Ichi where people aren't afraid to challenge each other, but also my incredible local community and like-minded friends who have very unique and diverse interests and passions. I’m also inspired by how my daughters see the world and the endless creativity they have. 

What professional legacy are you looking to create?

My goal as a leader is to build teams and cultures where people feel safe to challenge what's always been done, to advocate for what's right, even when it disrupts something comfortable. Throughout my career, I've had leaders say things to me that unlocked something in myself I didn't have words for yet, that encouraged me to lean into a passion or trust my own instincts. Those moments have stayed with me, and I want to do that for others. And in the cases where I already have, and someone has come back and told me that, I hold those moments really close.