Building stronger destinations through digital maturity
Wheresight partners with Destination & Tourism Organisations to measure, benchmark and impact the digital maturity of their operators.
We believe every destination’s success depends on the digital maturity of its operators. Wheresight was created to help tourism organizations understand where they stand digitally, how they compare to others, and where to focus next to achieve meaningful results. Built by the team behind Core Optimisation, Wheresight combines technology, data, and hands on consultancy to give destinations a clear picture of their digital maturity and the tools to drive improvement. Through our Digital Maturity Accelerator (DMA), we turn data into strategy and strategy into measurable growth.
Our Mission
Our mission is to empower destinations and operators to reach their full digital potential. We aim to close the gap between strategy and implementation, helping every partner we work with make better decisions, enhance visitor experience, and strengthen community outcomes. By uniting data, technology, and mentorship, Wheresight turns digital maturity into destination wide progress.
The Wheresight Approach
From assessing and benchmarking operators to delivering tailored roadmaps and guided mentorship, our approach helps DMOs turn insights into measurable progress — building stronger, more connected destinations through data, strategy, and support.
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We start by assessing every operator’s digital performance across five key pillars: leadership, people, customer experience, operations, and technology to understand where they stand today.
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Results are benchmarked against destination and peer averages to reveal patterns, strengths, and digital gaps. This helps identify where targeted support will drive the biggest improvement.
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Each operator receives a personalized roadmap outlining what to improve, how to do it, and when to take action, ensuring recommendations are clear, achievable, and measurable.
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Our experts work directly with operators to turn plans into real progress, providing ongoing mentorship that builds confidence, capability, and sustained digital growth.
Our Global Presence
With teams across Ireland, the UK, North America and UAE, we’re proud to support destinations worldwide. Our growing international presence allows us to share best practices, connect data across regions, and help destinations of all sizes achieve digital excellence.
Meet the Team
Caroline Dunlea
CEO and Co founder
David Brett
COO and Co founder
Karl Llewellyn
International Commercial Director
Susan Burke
International Account Director
Laughlin Rigby
Digital Transformation & AI Director
Gabbi Fogarty
Project Manager
Bridget O’Leary
Account Manager
Caroline Dunlea
CEO and Co founder
Caroline Dunlea is the CEO and Co-Founder of Wheresight and Core Optimisation. She brings over 30 years of diverse experience across travel and tourism, technology, SaaS, freight, and manufacturing. Her career has spanned customer focused businesses, giving her a deep understanding of leadership, commercial growth, and how digital transformation drives results at every level of an organisation.
Before founding Core Optimisation, Caroline served as Client Services Director at Avvio.com, where she led revenue growth, expanded global client portfolios, and became the face of the company’s digital innovation. It was there she discovered her passion for the transformative impact of digital on customer success and business performance.
As Co Founder of Core Optimisation, Caroline has continued to shape digital strategies for a wide range of clients and industries. Building on this experience, she co founded Wheresight in 2025 (a Core Optimisation company) to bring the same level of innovation and impact to the travel and tourism sector. Through Wheresight, Caroline helps destinations accelerate digital maturity, empowering DMOs and operators to make data driven decisions, improve visitor experience, and achieve measurable growth.
Beyond her leadership role, Caroline is a recognised advocate for women in business. She co founded KELLA, an organisation designed to cultivate meaningful connections among female leaders and tackle executive isolation. Her leadership has been recognised through several awards, including the Dublin Tech Summit Women in Tech Entrepreneur Award (2019) and finalist recognition in the EY Entrepreneur of the Year Awards, Emerging Category (2022).
David Brett
COO and Co founder
David Brett is the COO and Co-Founder of Wheresight and Core Optimisation. With over 20 years of experience leading teams in the digital and technology sectors. He has extensive experience working with both private and public sector businesses. In 2014, he co-founded Core Optimisation Ltd with Caroline Dunlea, creating a team of digital marketing experts who work with over 100 clients to enhance their digital presence through a combination of digital strategy, channel optimisation, data and digital transformation.
For the past 10 years, he has successfully steered Core Optimisation towards sustained growth and innovation, cultivating a results driven culture and fostering strong client relationships.
Under David’s guidance, Core Optimisation has become synonymous with excellence, delivering comprehensive digital solutions that drive business success. His strategic acumen and operational expertise have been pivotal in scaling the company, ensuring robust performance and continuous improvement. David has a proven track record in developing high-performing teams; he is an experienced mentor and talent developer.
He has an extensive understanding of the digital landscape and leverages his experience to navigate the complexities of the industry, positioning both Core Optimisation and Wheresight as leaders in their respective markets.
Prior to setting up Core Optimisation, David completed his Masters in E-commerce in 2003 and then joined Avvio as the first digital marketing hire in the booking and distribution technology company. He served on the management team at Avvio for six years, overseeing digital operations and product development. David has worked at the forefront of the development and delivery of Fáilte Ireland’s €60m Digital that Delivers programme and is the Co-Founder and COO of Wheresight, where he continues to drive operational excellence and meaningful digital maturity improvements for destinations.
Karl Llewellyn
International Commercial Director
Karl Llewellyn is the International Commercial Director at Wheresight, where he leads global expansion, shapes commercial strategy, and builds strategic partnerships that position the company for long-term success. With over 25 years of experience in business growth and international operations, Karl brings a deep understanding of how to scale organisations and unlock new markets.
Originally from Dublin, Karl relocated to West Cork more than two decades ago to expand his Business Process Outsourcing (BPO) company, Phonenet (later rebranded as Interaction) which specialised in customer service within the utilities sector. Under his leadership, the company grew to a workforce of 450 employees across six locations before being acquired in 2006.
Following the acquisition, Karl remained active in the BPO industry for over a decade, focusing on international expansion and strategic partnerships. In 2016, he founded Sanctify, a wellness-focused travel startup designed to help travellers make the most of their downtime on the road. While the business was disrupted by COVID-19 and later exited in 2024, the experience deepened Karl’s passion for innovation within the travel sector.
In 2025, Karl joined Wheresight, to bring his commercial acumen and entrepreneurial mindset to the global tourism technology space. At Wheresight, he works closely with DMOs, tourism boards, and partners across Europe, North America, and the Middle East to help destinations measure, benchmark, and improve digital maturity across their operator networks. His work continues to drive Wheresight’s mission, helping destinations use data and strategy to turn digital potential into measurable destination growth.
Susan Burke
International Account Director
Susan is the International Account Director at Wheresight, where she partners with clients to drive measurable digital maturity and long-term destination impact. With over 15 years of experience across tourism, hospitality, and digital transformation, she specializes in building trusted client relationships and turning strategic insight into measurable value.
Originally from Ireland, Susan began her career in the tourism and hospitality sector, working at Fitzgeralds Woodlands House Hotel & Spa in Adare, County Limerick, as Sales and Marketing Manager. There, she led sales strategy and marketing campaigns, gaining hands-on experience in revenue growth, stakeholder management, and delivering exceptional visitor experiences.
Transitioning into digital marketing, she spent several years at Core Optimisation as a Digital Account Manager and Client Success Manager. In these roles, she led multi-channel campaigns for tourism, retail, and B2B clients, specializing in client relationship management, data-driven strategies, and digital transformation programs. Her work included managing complex stakeholder networks and optimizing project delivery.
Since joining Wheresight, Susan brings a unique blend of client-first thinking, operational excellence, and strategic insight. She serves as the primary point of contact for clients, guiding onboarding, adoption, and long-term growth, while ensuring programs deliver measurable value. Passionate about helping destinations thrive, she focuses on turning data, strategy and innovation into tangible results for tourism organizations and their stakeholders.
Laughlin Rigby
Digital Transformation & AI Director
Laughlin Rigby is the Director of AI & Digital Transformation at Wheresight, where he leads product and delivery of the Digital Maturity Accelerator for destinations. With two decades across tourism, media and technology, he helps DMOs and operator networks become digital-ready—using data, structured content and practical roadmaps to lift conversions, quality and measurement.
Originally from Ireland, Laughlin brings 20+ years of digital leadership across tourism, media and high-growth tech. He began his career at Unilever before moving into national destination marketing with Tourism Ireland, where he led the development of discoverireland.com across 23 country sites as well as launching numerous global brand campaigns for Ireland. He later founded Travelshake.com, an early social platform for the travel industry and led the marketing team for the award-winning Gathering Ireland tourism initiative. He then went on to senior marketing roles with Visit Sunshine Coast in Australia, The Irish Times and Glenveagh Properties PLC.
In 2024, Laughlin became Director of AI & Digital Transformation at Core Optimisation, establishing AI governance, digital transformation playbooks and measurable, cross-functional programmes for tourism boards and operators. In 2025 he joined Wheresight to lead its Digital Maturity Accelerator (DMA): the benchmarking, dashboards and enablement framework that helps destinations measure, compare and improve the digital performance of their member operators.
At Wheresight, Laughlin partners with DMOs, tourism boards and government programmes across Europe, North America and the Middle East to roll out the DMA programme end-to-end—audits and benchmarking, clear roadmaps, and hands-on enablement. His focus is on destination performance fundamentals: structured content and accurate listings, accessible and high-performing websites and booking platforms, consistent brand/application standards, and robust data foundations that support better AI transformation and better decisions.
Gabbi Fogarty
Project Manager
Gabbi is an accomplished professional with extensive experience in digital transformation and project management. Since 2021, she has served as a Project Manager on the Digital That Delivers programme, leading initiatives that drive the digital transformation of visitor attractions across Ireland. In this role, Gabbi has successfully delivered projects that have strengthened the digital presence and operational performance of a wide range of attractions, events, and festivals.
Biography
In addition to her work on Digital That Delivers, Gabbi has contributed to business development efforts promoting Irish visitor attractions internationally particularly within the U.S. market helping to expand their reach and growth potential. Her expertise spans the broader tourism industry and extends into related sectors such as retail and e-commerce, giving her a well-rounded understanding of digital strategy and customer engagement across industries.
Bridget O’Leary
Account Manager
Bridget is an Account Manager for Wheresight. Passionate about blending creativity, strategy, and technology, Bridget helps destinations and tourism businesses navigate their digital transformation journey. With a background in tourism, hospitality, and marketing, she brings a people-focused approach to digital innovation and project delivery.
Bridget holds a degree in Business and Tourism Management from Munster Technological University, graduating in 2019. Her career began at Adare Manor Hotel and Golf Resort in 2018, where she progressed from Hostess to Wedding & Events Coordinator, gaining invaluable experience in client relations, event management, and the delivery of world-class hospitality. During this time Bridget also graduated Limerick Insitute of Technology with a certificate in Psychology as a passion project to further deepen her understanding of human behaviours.
In 2022, she joined House Bar & Restaurant in Limerick as a Sales and Marketing Executive, leading campaigns that strengthened brand visibility and engagement. This role deepened her interest in the connection between tourism, storytelling, and digital strategy.
Since 2023, Bridget has worked as a Project Coordinator for Digital Transformation projects, supporting Destination Management Organisations (DMOs) and tourism enterprises in embracing technology to enhance visitor experiences, streamline operations, and future-proof their growth. She is passionate about helping destinations evolve in a way that keeps digital innovation grounded in human connection and authentic storytelling.