Thursday 14th October 2025
11:30 - 15:30
The Lookout, London
Insight is delighted to host the fourth exclusive event in our roundtable series, featuring our guest speaker, Stefanie Sword-Williams. Stefanie is the founder of platform and event series F*ck Being Humble, and an expert on building meaningful workplace relationships. She will share how to build relationship currency, identify key influencers, and proactively advance your career – encouraging you to don't wait to be invited, invite yourself. We’ll delve into the power of active sponsorship, understanding how individuals and the organisation can champion talent, as well as the importance of effectively advocating for your own ambitions.
The event, hosted over lunch, will also provide a valuable networking opportunity with fellow professionals.
Please register now to avoid disappointment as spaces are limited.

11:30 – Guests to arrive
11:50 – Welcome and introductions
12:00 – Keynote speaker - Stefanie Sword-Williams
12:25 – Seated lunch and networking
14:30 – Panel discussion (Tea / coffee)
15:00 – Closing remarks and key takeaways
15:30 – Event close
#1
Learn directly from F*ck Being Humble founder Stefanie Sword-Williams and other industry leaders how to actively champion your own career.
#2
Network with fellow professionals and explore the critical roles of active sponsorship and self-advocacy.
#3
Gain Insights into the essential tools and strategies that will empower female tech leaders to make significant strides in breaking the glass ceiling.
#4
Enjoy a dining experience at
The Lookout, London, on level 50, offering uninterrupted views of the city's iconic landmarks.
Karen has over 20 years of experience in the Services business and joined Insight in March 2019 to run the EMEA Services Organisation. She previously worked at DXC, formerly CSC, where she held the position of Vice President UKIIMEA Delivery. Karen’s track record includes running international roles, building large scale Managed Services business, and driving acquisition integrations and transformation initiatives. She is based in Northwest England and is an active participant in the Northern Woman Initiative to bring equality and social balance across the UK. Karen is also a passionate STEM volunteer, working in schools and colleges in the local area.
With over 30 years of experience in the IT industry, Gill Holloway is dedicated to creating and enhancing strategic alliances that support expertise and ambition while delivering exceptional client experiences and promoting environmental sustainability. Skilled in strategy formulation, Gill excels in creating clarity and inspiring teams to execute effectively. Gill was honoured as the UK CRN Executive Mentor Winner in 2023 for significant contributions to developing the next generation of talent. Passionate about driving successful business transformation and innovation, Gill cultivates a high-performance, ethical culture with a technology-centric, business-outcome engagement approach.
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Nicola Mills is a seasoned technology leader with 20+ years of experience. Before joining Insight, she held Delivery and Sales leadership roles at some of the UK’s leading System Integrator fi rms, driving customer success, growth, and innovation. As Insight’s Director of Solutions, Nicola spearheads the solutions sales team and the UK solutions business. She champions diversity in her teams to foster diverse perspectives, driving strategic vision and execution to deliver transformative solutions that align with customers’ business objectives.
Peter Rising is a Microsoft Most Valuable Professional (MVP) and Senior Practice Lead for Cyber Security at Insight, supporting the EMEA region. With over 30 years in IT, he’s known for his expertise in Microsoft 365, Purview, and security technologies. He shares tutorials and certification tips through his YouTube channel and published work. Peter is a passionate advocate for women in tech and mental health awareness, and is a trained Mental Health First Aider. He actively promotes inclusion and wellbeing across the industry.
Stefanie is an accomplished author and dynamic speaker renowned for her expertise in building meaningful workplace relationships and advocating for career growth. As the driving force behind the "F*ck Being Humble" movement, Stefanie empowers individuals to embrace self-advocacy and proactive career management. Her insights, drawn from extensive experience and her acclaimed book, focus on actionable strategies for networking, self-promotion, and identifying opportunities, making her a leading voice in professional development.
Barbara is the Global Head of Industry and Value Consulting at Stripe where she leads the revenue growth strategy, and works with enterprise customers to grow their businesses. She is also the CEO of Stripe Technology Europe, Stripe’s regulated business in the EEA. Formerly a Partner with McKinsey & Co, she supported global consumer facing companies to transform and grow their businesses. She is a chartered engineer and MBA graduate.
Ashley is a people-focused change leader with vast experience driving transformation across complex organisations. Her career has centred on continuous improvement through teammate-centric initiatives that create clarity, enhance collaboration, and maximise technology use. As Chief of Staff for Insight EMEA, Ashley bridges the gap between people and technology—empowering clients and teammates to achieve more in their everyday work. She is equally passionate about inclusive workplaces and inspiring future leaders, championing grassroots change, hosting hackathons for young people, and volunteering as a Scout Leader.
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