People & HR Director || Technology Start-Ups & Scale-Ups

I specialise in helping private equity–backed and investor-led businesses realise value through people, leadership and operating execution, particularly across FinTech and Financial Services environments undergoing growth, acquisition and transformation.

My work often starts at the point where transactions become reality. I support Boards, investors and executive teams to translate deal intent into scalable operating models, leadership capability and organisational structures that protect value, accelerate performance and enable sustainable growth beyond Day One.

Over the past decade, I have led complex integrations, carve-outs and restructurings across international markets, including the acquisition and integration of global businesses within regulated financial services and high-growth technology sectors. This has included scaling organisations across multiple geographies, building enterprise-grade people and governance frameworks, and supporting successful exits for institutional investors.

I am particularly effective in entering businesses to assess, stabilise and strengthen leadership, reduce people-related execution risk, and align workforce strategy to commercial ambition. While not a career “BAU HR leader”, I step into operational leadership roles where required, with a mandate to professionalise, simplify and leave behind stronger capability.

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WHAT OTHERS SAY

"Dylan guided the Board with regards to leadership transition at the Company, and executed with integrity and action throughout the restructuring and acquisition programme."
- Farooq Jaffrey, Fintech Venture Capital Investments

"As COO, Dylan worked closely with the CEO to implement a turnaround strategy and successfully positioned the company for its successful acquisition by Trading Technologies."
- Mark Rodrigues, Venture Partner, Illuminate Financial

"In an extremely fast moving and challenging environment, Dylan joined the Integration Team leading the People, Culture and Comms workstream of 200 people from Reg-Room and Thompson Reuters Regulatory Intelligence into CUBE. He hit the ground running, prioritising and delivering urgent and strategic requirements from his first morning."
- Andrew Scola, M&A Director, ex Deloitte, PwC

"What Dylan doesn't know about M&A you could write on your toenail!  He is super knowledgeable, knows his way around M&A like the back of his hand and is SUPER patient. He is objective, thoughtful and puts the employees first - always."
- Elinor Brett, FCIPD, CPO

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Dylan Roberts

Most M&A deals that fail don't fail in Excel, or in a deal sheet. They fail in Teams and random corridor conversations.

If you tackle an acquisition or a carve out, and don’t have a clear people integration plan front and centre, you’re not managing risk. You’re deferring it.

Successful PE models assume execution. People determine whether execution actually happens.

People risk is deal risk. Ignore it at your peril.

#mergersandacquisitions #peopleintegration #privateequity

Interim People Leader | HR Change & Transformation | M&A People Integration | Executing the People Agenda for PE-Backed Firms

Polly Barnfield, OBE

Maybe* Tech CEO | Creator of Social Media Management Platform I High Street Task Force Partner I Senior Fellow IPM I Social Entrepreneur | 3x Founder | Mum

I’m building AI Agents that get work done.

AI should not feel experimental, intrusive, or fragile. It should be trusted, invisible, and embedded into how teams already work.

Through training more than 25,000 businesses and interviewing over 1,000 leaders for The Big AI Secret research, we uncovered a consistent pattern. Most organisations are already using AI, but very few trust it with real work. The result is tool sprawl, duplicated effort, and thousands of hours lost every year moving information between disconnected systems.

The problem is not a lack of AI capability.
It is a lack of execution.

What We Built

I’m the CEO of Maybe*, a platform designed to help organisations stop experimenting with AI and start operating it.

Maybe* deploys AI Agents that work inside Slack or Microsoft Teams, connect to the tools teams already use, and take ownership of defined workflows. Teams can start with ready-made Agents and scale safely using our patent-pending AI Agent Builder, without adding complexity or risk.

Our customers use AI Agents to generate reports, create on-brand content, support customers, and coordinate work across more than 2,000 tools. The focus is simple: measurable outcomes, delivered reliably.

Why This Matters to Me

Before Maybe*, I spent over a decade building technology that helped raise more than £40 million for charities by embedding giving into everyday online behaviour. That work earned me an OBE and shaped how I think about technology.

The lesson was clear:
the most powerful technology is invisible to the people it serves.

That belief drives everything we build at Maybe*. AI should amplify people, not overwhelm them. It should feel like part of the team, not another system to manage.

Where We’re Going

AI will not replace teams.
But teams that operate AI well will outperform those that do not.

My focus is on building AI Agents that organisations can trust with real work, at scale, without needing to become technical experts.

That is the future we’re building at Maybe*.

A Personal Note

I do my best thinking while walking my greyhound. Before building technology companies, I won a gold medal riding horses, which taught me that discipline, consistency, and trust matter more than speed.

I’m also a mother, a grandmother, and an enthusiastic jam maker. Whether it’s training a horse, building a business, or getting jam to set, I believe you either do it properly or you don’t do it at all.

👉 Start free: https://maybetech.com
📊 Read The Big AI Secret research: https://maybetech.com/ai-research

Founder and CEO

Maybe* is an AI-powered that helps ambitious businesses transform their digital communications

In one easy-to-use platform, we deliver:

1. Personalisation at speed: Harness AI to elevate your work efficiency.
2. All-in-one digital suite: From social media to CRM, access a comprehensive range of digital communication tools in one seamless platform.
3. Smart automation: Ensure your message resonates at the perfect moment and follow up flawlessly.
4. Targeted AI-Driven Ads: Position your message directly in front of your desired audience.
5. Unparalleled Support: Benefit from our 24/7 expert assistance.

> Explore Maybe* with a free trial at www.maybetech.com
> Do your best work faster: Join our Masterclass  www.maybetech.com/masterclass.


Maybe* is a proud collaborator in the UK Government's High Street Task Force, a five-year initiative fostering High Street rejuvenation. We're committed to helping local UK businesses amplify their digital presence, connecting them more effectively with their customers.

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Dylan Roberts

Polly Barnfield, OBE

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The Battle

Dylan Roberts

Polly Barnfield, OBE

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Dylan Roberts's LinkedIn Performance

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