The 2025 Remote Leadership Awards: Leaders Who Evolved Beyond the Office

Which leaders pushed remote work forward last year?

If you thought 2023 and 2024 were career-defining years, I hate to break it to you, but they were warm up laps. This past year has seen remote work become a vital platform for leaders working with AI. A veritable launch-pad for AI-first leadership.

The combination of total flexibility and mastery in artificial intelligence made it an incredible year of drastic upheavals, mega-change and product iteration like we’ve never seen in tech before.

This past year was not like the others.

Remote work became an endangered species, as most leaders sauntered back to their cubicles. The ability to properly harness the world-shaking power of AI at work is nearly as rare now. But those who managed extraordinary feats are pulling ahead so far, they’re launching into orbit.

It’s not a gap or a chasm –it’s an interplanetary leap. And I’m not being dramatic enough.

So, this year the Remote Work Leadership Awards asked a simple question: Who’s been deep in the remote-AI trenches and has figured out the next phase of work?

There are 10 people here who did the work of combining brains, bandwidth and bots in ways we’ve not experienced until now.

These remote leaders weren’t adapting – they were evolving.

Yes, yes I know. AI loves to write about ever-evolving this or that. But as it turns out – there were wisdom in those overused words.

The Next Layer of Intelligent Leadership is AI

You can no longer be a high performing remote leader without AI – that’s a done deal.

But there’s a difference between leaders who skate the surface of its potential, and those who truly embrace it as an external layer of intelligence to supplement their own.

A layer that augments their thinking.

We’ve spoken about our belief in top performers being the harbingers of the future, and unlocking AI’s infinite potential. We’ve touched on AI tools, building with AI and metacognition as the highest form of intelligence.

As we waded through these nominations I kept wondering – who embodies this progress? Who isn’t just using or adjusting to AI? Who sees the scale and is evolving along with it?

You hear it everywhere you go.

“AI is a tool.”

Well, I’m happy to tell you – it’s not. Once upon a time I believed this too. I work with artificial intelligence every day, experimenting with automation and system building.

And still, I categorized AI, this amorphous collected of functions – this DIY brain, as a tool. It’s not a tool. No more than our own brains are tools.

I also once said that AI is a mirror. But it’s not that either.

While in its novice form, it does tend to hug the reflection of its creator – it’s also so much more than simply who or what we are. AI, is something different entirely.

It’s something more than a tool. More than us.

As the brightest minds in the world work feverishly to tame the wild beast of agentic AI and the impossibly possible architectures and products that are emerging – one thing is fundamentally clear.

AI belongs to us, sure. But increasingly, it also belongs to itself.

And that’s what will define the next generation of remote-AI leadership.

Those who understand intelligence - where AI ends, and where our uniquely human thinking begins, are already shaping the way EVERYONE (in and out of the office) will work in the coming days.

While the old guard clung to stand-ups and free cafeteria coffee, the real leaders of 2025 embraced evolutionary intelligence and now - the asteroid is here.

The Remote Work Leadership Awards (2025): Winners

1. Ethan Mollick (Voice of The Future of Work Award)
2. Rahul Subramaniam (Remote Work Leader Award)
3. Anirudh Shrikanth (AI Innovator Award)
4. Leslie Perlow (Work Life Hero Award)
5. Todd Ramsey (Remote Team Culture Award)
6. Shannon Ramsey (The Voice of Reason Award)
7. Shreya Mahendru (The Short Storyteller Award)
8. Al Dea (Podcaster of The Year)
9. Manuel da Silva (Knowledge Builder of The Year Award)
10. Dante Disparte (Instigator Award)

Congratulations to 2025’s winners!

1. Voice of The Future of Work Award 2025: Ethan Mollick

This award celebrates a rare kind of remote leader - someone who comments on change but also writes prodigiously to help us understand it.

While most people are chasing AI trends or doomscrolling LinkedIn hot takes, Ethan Mollick is out here building new maps, mental models and frameworks. He takes the organically technical and shows us what that looks like in the real world.

Ethan’s an author, a Wharton professor, a researcher, and (whether he likes the label or not) one of the most essential voices of this burgeoning remote + AI age.

He was 2025’s sense maker in chief – for many of us.

Through his compelling writing, imaginative teaching, and relentless exploration of generative AI’s potential and pitfalls, Ethan’s become the unofficial codebreaker for the future of work. He gives us sense, at a time when many are running on misinformation and confusion. That’s saying a lot.

In terms of evolutionary intelligence - Ethan is operating at the sensemaking layer - the realm of fact over assumption, foresight over fear. The place where real leaders live when everything is ambiguous, fast, and frequently quite weird.

He’s shown us not just what’s happening - but how to think about what’s happening.

The Voice of the Future of Work Award goes to Ethan Mollick for his unmatched ability to frame complexity with clarity, and for helping millions navigate the messy intersection of AI, work, and what it means to be human.

If leadership is knowing what to do next, Ethan’s one of the few making that feel possible.

• Follow him on LinkedIn for his best content.
• Read his books here.
• Check out his Substack One Useful Thing.
• Follow him on X and Instagram.

2. Remote Work Leader Award 2025: Rahul Subramaniam

This award goes to the kind of leader who proves what remote work sceptics still can’t wrap their heads around - you don’t need proximity to drive top performance, you only need systems.

Rahul Subramaniam is the CTO of EWS Capital, leading multiple teams across time zones, roles, and products. He oversees the top 1% of tech talent and manages to outdo them. But talk to anyone who reports to him, and you’ll hear the same thing.

They don’t know how he does so much - it just works.

Whether it’s 8 am on a Monday or 6 pm on a Saturday, Rahul shows up - not with outdated micromanagement, but armed with empathy, trust and airtight coordination.

He’s been a major player in redesigning leadership itself for a remote-first, AI-forward world. His colleagues describe him as endlessly available, absurdly efficient, and somehow always one step ahead.

This is a leader who listens deeply and responds decisively – plus he turns half-baked ideas into concrete direction - usually in under 15 minutes.  

The real trickery is that he doesn’t scale by adding layers. He scales by building autonomy-friendly systems - outcome-complete roles, spotless processes, and team structures that don’t need never-ending oversight to blaze ahead at full speed.

As one teammate put it - “He guides me, supports me, and helps me grow. That’s leadership in every sense of the word.”

Rahul excels at the system-design layer - the layer where real leadership lives when you replace supervision with structure, and presence with tangible outcomes.

The Remote Work Leadership Award 2025 goes to Rahul Subramaniam for showing us that the future of leadership isn’t about being everywhere - it’s about building systems that don’t need you to be.

• Follow him on LinkedIn.
• Listen to his podcast ‘AWS Insiders’

3. AI Innovator Award 2025: Anirudh Shrikanth

This award honors someone who didn’t just adopt AI - he used it so effectively in his work it replaced entire teams of people.  

When Anirudh Shrikanth joined EduPaid as its sole engineer, the product didn’t exist yet.

It was an idea, and a long road ahead. Less than a year later, there are three live platforms, over $2 million in annual processing, and a growing team building on top of the system he architected.

Anirudh didn’t only build fast - he built with expert care.

His approach balances deep technical thinking with a clear sense of where AI can help, and where human judgment has to stay in control. He’s not chasing automation for its own sake.

He’s asking smarter questions: Is this necessary? Does it scale? Does it make the work better?

At a time when AI is being thrown at every problem, Anirudh stands out for his ability to design systems that are both AI-aware and human-centered.

He uses AI to remove blockers, not replace thought.

This is leadership at the external cognition layer - where AI becomes a second intelligence, used deliberately to enhance autonomous precision, speed, and scalability, while keeping human decision-making at the core.

The AI Innovator Award 2025 goes to Anirudh Shrikanth, for setting a new standard in AI engineering. These are thoughtful, scalable systems that integrate AI without losing sight of the people and decisions that matter most.

• Follow him on LinkedIn.

4. Work Life Hero Award 2025: Leslie Perlow

This award recognizes leaders who understand something most workplaces still haven’t fully grasped - intelligence wilts under exhaustion, and joy is not optional - it’s performance fuel.

Leslie Perlow is the Konosuke Matsushita Professor of Leadership at Harvard Business School and one of the best voices in research on how work and life can reinforce each other instead of compete.

In her work on how busy, high‑achieving professionals find joy, she and her co‑authors show that joy isn’t a luxury or a nice to have. It’s more of a practical ingredient for sustainable performance, and real leaders have to make room for it.

Instead of glorifying exhaustion as so many tech companies do, Perlow reframes work life around what she calls meaning, achievement, and joy.

Her research - including tools like the Life Matrix and experiments in shaping better work time - highlights that when people protect space for rest and positive emotions, they feel better AND perform better.

Perlow is outstanding at the energy regulation layer - she knows that burnout is a system failure, not some twisted badge of honor. So, she designs environments that protect focus, rest, recovery, and joy as a performance must-have, not a distraction.

Leslie’s research and writing challenge the ‘more work, more output’ assumption.

She shows that urgent doesn’t have to mean triumphantly unhinged, and that sustainable pace is not weak - it’s strategic. It’s proof that ambition and humanity can coexist -and that work that allows joy compounds our success as leaders.

The Work Life Hero Award 2025 goes to Leslie Perlow for proving that designing for joy, rest, and meaning isn’t a luxury - it’s a smarter, more human way to power high performance at scale, even with AI snapping at our heels.

• Follow her on LinkedIn.
• Read about her work at Harvard Business School.
• Read her ground-breaking article on time well spent at MITSloan.
• Explore her research.

5. Remote Team Culture Award 2025: Todd Ramsey

This award goes to a leader who didn’t just make remote work viable - he made it structured, transparent, and enduring.

As CRO of Skyvera, Todd Ramsey took what was once a bloated function and rebuilt it with just three people - without burning them out or slowing things down.

That kind of performance doesn’t come from over-managing. It comes from building deep alignment, smooth workflows, and a shared sense of responsibility.

Todd isn’t the type to talk about culture - he just builds it into everything his team does.

His team operates with consistency, confidence, and speed and it’s because everyone knows how the work moves. They don’t compete with each other, they compete with what’s possible.  

Todd is great at the social coordination layer - the ability to set up behavioral patterns, mutual expectations, and working norms that remove the need for constant check-ins or performance theater.

He’s managed to make this instinctive - and it shows in how his team shows up.

Remote culture isn’t PS5 rooms, Zooms and Slack status updates. It’s how well people build together when things get hard. It’s a set of shared values baked into every action.

That’s the culture he’s built.

The Remote Team Culture Award 2025 goes to Todd Ramsey for proving that the most effective remote cultures aren’t pretend - they’re in the DNA of everything we do.

• Follow him on LinkedIn.
• Find him on X.

6. The Voice of Reason Award 2025: Shannon Ramsey

This award honors a leader whose strength isn’t just execution - it’s judgment.

Shannon Ramsey, SVP of Commercial at Aurea Software and Jigsaw, is the one teams turn to when things get complicated, uncertain, or emotionally charged. She doesn’t have all the answers - but she knows how to think when it matters.

Must be her background in psychology doing the heavy lifting!

Her team calls her the rock. The gravity that holds everyone together. The person who sees the issue before it becomes a problem - and then helps everyone else see it too.

In fast-paced quarters, during SEV1 customer issues, or in the middle of tough renewals, Shannon is the one who brings the temperature down without lowering the bar. She sees people clearly - not just what they can do, but what they’re still growing into- and she guides them forward.

She doesn’t throw people into the fire. She steps in with them.

Shannon led her team to double their annual goals - with 50% less people than previous years. But what makes her stand out isn’t just what she achieved. It’s how she leads when everything’s on the line - with steadiness, discipline, and empathy.

Shannon is brilliant at the judgment layer - where leadership isn’t about ideology or ego, but it does help if you know what matters, what doesn’t, and what to do next. She cuts through panic, defends nuance, and helps teams think better.

The Voice of Reason Award 2025 goes to Shannon Ramsey for being the stabilizing force behind the scenes – invaluable in the age of AI where calm is key.

• Follow her on LinkedIn.
• Find her on X.

7. The Short Storyteller Award 2025: Shreya Mahendru

This award goes to a rare kind of digital doer who can fit a full career lesson into a single scroll. Someone who can tell a good story and inspire change through media.

Shreya Mahendru is a digital storyteller, remote work advocate, and global freelancer who lives in Thailand when she isn’t travelling.

Whether she’s breaking down career pivots, freelance red flags, or how to work remotely like a pro, Shreya keeps it short, smart, and practically useful.

She’s out here to make bold ideas around remote work stick - and give you something you can use in your own career five minutes later.

Shreya is great at the compression layer in action - where intelligence spreads not by saying more, but by building community around punchy universal truths.

Shreya turns vague concepts into crystal insight without losing the nuance – and she doesn’t chase clout. It’s collective sense-making in snackable form. With today’s attention spans, that matters more than ever.

The Short Storyteller Award 2025 goes to Shreya Mahendru for making thinking contagious - and proving that you don’t need books or essays to changes people’s minds about remote working.

• Follow her on LinkedIn.
• Find her on Instagram, or YouTube.

8. Podcaster of The Year 2025: Al Dea

This award goes to the podcaster who treats every episode like a systems upgrade for how we work.

Through his podcast, The Edge of Work, Al Dea has carved out a space for meaningful exploration of how work is changing - from distributed teams and AI disruption to career growth and leadership in a post-office world.

Al’s a consultant, facilitator, keynote speaker, and podcast host with a background in Deloitte and Salesforce, and his insights have appeared in outlets like Forbes, Fast Company, and Business Insider. 

His podcast brings together leaders and thinkers to explore the major shifts happening in talent, leadership, culture, and how work gets done - especially in an era of distributed teams and accelerating AI.

Each episode is a reasoned conversation about what’s changing, why it matters, and how people navigate those choppy waters.

Al’s a thought leader and host who has perfected the distributed cognition layer - where ideas become part of the collective mind rather than sitting in individual heads.

The Edge of Work acts like an external memory and shared reasoning system, helping listeners connect dots across leadership practice, talent development, and the future of work. Nice!

Mostly his episodes raise the level of the conversation on remote work, leadership, and the real impact of technology. The result is a body of work that helps thousands think more clearly about the world of work, together. Time to subscribe.

The Podcaster of the Year Award 2025 goes to Al Dea for shaping long‑form dialogue into a tool for collective understanding - building intelligence one conversation at a time.

• Follow him on LinkedIn.
• Listen to The Edge of Work Podcast.
• See his website.
• Read his Medium blog.

9. Knowledge Builder of The Year Award 2025: Manuel da Silva

This award goes to someone who understands complex systems so well - that he shares that understanding simply in ways that make everyone around him smarter.

Manuel da Silva, a customer support and customer success professional from Brazil who calls himself a CS Cyborg because of how he uses AI in his daily work, has become a go‑to source of practical thinking and public knowledge.

Whether he’s breaking down system architecture, documenting technical workflows, or sharing how he uses AI to augment his thinking, Manuel practices a rare form of transparency: thinking in public.

He doesn’t chase attention or popularity. He trades in durable understanding - the kind that outlives a single post or hot take and lifts the baseline intelligence of the communities he touches.

Across platforms, teams, and conversations, Manuel consistently translates technical depth into usable insight. He mentors across time zones, contributes original thinking, and opens the door for others to build with him - not just follow behind.

He practically integrates AI into his workflow and then shares what works, what doesn’t, and what others can borrow.

Manuel excels at the knowledge externalization layer - where intelligence stops being personal and becomes transferable. He doesn’t hoard knowledge. He makes it accessible, durable, and shareable - long after the meeting ends.

The Knowledge Builder of the Year Award 2025 goes to Manuel da Silva for his generous, thoughtful, and consistent effort to raise the collective intelligence of every remote team he touches.

• Follow him on LinkedIn and X.
• Watch his Crossover story here.
• See his inclusions here, and here.

10. Instigator Award  2025: Dante Disparte

This award goes to a leader whose voice enters a debate and then reshapes the conversation.

Dante Disparte serves as Chief Strategy Officer and Head of Global Policy at Circle, the global financial technology firm behind the widely adopted USDC digital currency - a settlement layer that supports trillions of dollars in internet transactions and underpins borderless digital commerce.

Across finance, risk, and public policy, Dante’s career has been about moving systems that many assumed were immovable - global payments infrastructure, regulatory frameworks for emerging technology, and the relationship between innovation and security.

He’s also a founder of strategic advisory Risk Cooperative, serves on the World Economic Forum’s Digital Currency Governance Consortium, and contributes to global discussions on competitiveness, economic resilience, and the future of global markets. Shew.

Dante’s advocacy for human‑AI collaboration, economic inclusion, and interoperable digital money pushes industries and governments toward frameworks that treat innovation as a shared problem, not a siloed advantage.

He engages regulators, educators, and technologists by anchoring arguments in systems logic and authentic global context.

Dante excels at the evolutionary pressure layer – as a remote leader who introduces necessary discomfort that forces adaptation without nihilism or chaos. He challenges norms not to overturn for shock’s sake, but to clear the way for more resilient, equitable, and forward‑looking systems.

The Instigator Award 2025 goes to Dante Disparte for being a catalyst and for insisting that evolution in technology, finance, and work happens when influential voices refuse to accept “this is how it’s always been done.”

• Follow him on LinkedIn.
• Find him on X.
• Check out his website.

Congratulations to The Remote Work Leaders Who Won!

This year’s winners showed us something far, far deeper than great remote leadership. They showed us evolutionary intelligence in action.

Can you believe that we’re here?

The world is still hanging onto outdated models, but these leaders don’t care. They built smarter systems, fairer models, and more durable ways of thinking for all of us.

Some operated at the surface - shaping better toolsets, faster feedback loops, and effortless workflows. Others worked behind the scenes - refining judgment, protecting team energy, and embedding new knowledge into how we lead and collaborate.

These are the people using remote work and AI to create a new way of working.

They’re plugging into the true power of technology, every day.

The next era of remote leadership will challenge all of us to use AI as another layer of intelligence augmenting our own. We’re seeing glimpses of what could be!

This is systemic. This is evolution in action.

So to every remote worker out there -

Keep experimenting. Keep speaking up. Keep pushing back on the idea that intelligence lives in offices and great things can only be created in stuffy conference rooms.

These leaders didn’t wait for permission. They built what was missing. And they made the future of work smarter, fairer, and more human for the rest of us.

Follow them. Learn from them.
And maybe next year - join them.