CISHRP Annual Conference theme for 2026 is
Work Reimagined: Designing organisations for a changing world
29th May 2026
Hotel Indigo, Grand Cayman
Keynote Speaker - Heather Elkington
Heather Elkington began her career as an Assistant Manager on the Harrods shop floor.
She went on to help scale the SaaS company GoProposal to multi-million-pound revenue and an eight-figure exit, before joining Sage (FTSE 100) as Director of Operations, leading five high-performing teams.
After seeing how outdated most management training had become, Heather Elkington founded Fresh Leadership World, which has now trained over 5,000 managers worldwide and reached tens of millions online.
Her clients include global organisations such as Sony Music Publishing, the Ministry of Defence, Abercrombie & Fitch, American Express and Specsavers. She is a TEDx speaker, her talk ‘How to Manage Gen Z’ having amassed a staggering 18,000 views and a Penguin-published author.
Heather’s debut book, ‘Your Boss Era,’ offers a refreshing, practical guide to modern management with honest storytelling to help leaders make a real impact in the workplace. Her work has been featured in GQ and Forbes, and her candid, evidence-based approach has made her one of the most trusted voices in leadership today.
Warm, grounded and deeply engaging, Heather’s speaking style turns complex leadership challenges into clear, actionable insights. She leaves audiences inspired to think differently about what great management can look like and equipped to make it happen.
Speaker - Kylie Rae Fitzgibbons
Kylie Rae Fitzgibbons, known as kylieraeofsunshine, is a dynamic hospitality leader, international keynote speaker, and experience strategist with over two decades of expertise elevating service standards across the United States and the Caribbean. With nearly eight transformative years in Grand Cayman, she served as a pre-opening Director at the Kimpton Seafire Resort + Spa. Forever grateful to help shape one of the region’s most celebrated luxury guest experiences, now recognized globally.
A self-declared international ambassador of “Caymankind,” Kylie Rae brings a signature blend of warmth, strategy, and human connection to every room she enters. Her signature message, “Service with a Smile Starts With You,” challenges leaders and teams to look inward first. You will leave the session re-engaged by activities that demonstrate that exceptional service begins with mindset, ownership, and authentic care.
Through storytelling, actionable insights, and contagious energy, Kylie Rae inspires organizations to turn everyday interactions into unforgettable transformational experiences one smile at a time.
Speaker - Paul Krismer
Paul Krismer teaches the practical application of positive emotions to achieve corporate and personal excellence. At no time in our modern life has this message been more important. With economic, epidemic stress, and political issues creeping into every part of people’s already demanding lives, Paul provides the HOW of resiliency and the POW of effective culture!
He is recognized as one of the top ten most notable speakers by Ignite Magazine‐The Magazine for Professional Meeting Planners. He is equally comfortable on a stage as he is delivering virtual content all around the world.
Paul is an employee engagement and workplace culture expert and a dynamic speaker/trainer. Playful and captivating storytelling complements his informative and entertaining presentations on the science of happiness as a strong predictor of success. At the same time, Paul is exceptionally practical, providing tools that audiences and entire workforces can immediately use.
Adding to this scientific foundation, Paul draws on real‐world experience using the tools he shares. For more than 30 years, he implemented the lessons from positive psychology research while working in senior management roles—overseeing hundreds of employees, multi‐million‐dollar projects, and cheerfully growing future leaders. In addition, as a Certified Executive Coach, Paul has helped his clients discover hidden talents and attain greater life satisfaction.
Speaker - Jackson Kerchis
Jackson Kerchis is a former strategy & operations leader, startup executive, and Zen monk. He’s a co-founder and partner at Happiness Means Business and Warrior Leader Training Companies where he helps business and military leaders solve their people problems. He applies research from psychology and social sciences to improve employee experience and business performance.
Notable clients include the Army National Guard, Vivint home security, UAB health system, and Young’s Commercial (the largest produce hauler in the US). His firm has developed solutions to re-engage executives struggling with work-life balance, improve frontline supervisor leadership, drive $3M in operations improvements, and support soldier staffing / mental health.
Jackson created the world’s first major in Happiness at the University of Alabama where he taught the school’s first ever happiness course and now offers a course on the Science of Happier Work. He also holds an executive coaching diploma from Emory’s Goizueta Business School. He is the author of two books including Beyond Profit & Productivity: Putting Positive Workplace Culture to Work – an Amazon best seller. He is a frequent speaker at association conferences and company events.
Speaker - Nick Joseph
Nick Joseph is the Founder and Managing Director of Reside Cayman Ltd., a leading immigration services company in the Cayman Islands. A Caymanian Attorney-at-Law since 1997, he has over 25 years’ experience advising on immigration, employment, and relocation matters. Nick previously led local legal teams at two major firms and is widely respected for his deep knowledge of Cayman’s immigration framework. He has served on several government committees, including the Immigration Review Team, and is an Accredited Mediator and Notary Public. Nick also and delivers seminars for business and HR professionals regularly.
Speaker - Gloria McField-Nixon
Gloria McField-Nixon, Cert. Hon., JP, is the Deputy Governor Designate for the Cayman Islands Government, due to commence her new role on 8th July 2026. Currently the Chief Officer for the Portfolio of the Civil Service (PoCS), Mrs. McField-Nixon provides strategic leadership for government-wide human resource policy, public sector reform, and corporate governance, supporting a workforce of more than 5,000 employees. A highly respected public-sector leader, she has nearly three decades of experience across multiple ministries and has played a central role in advancing the Civil Service’s transformation agenda, including the delivery of two successive Strategic Plans focused on creating a world-class organisation. This progress has been closely monitored since the strategy’s inception in 2018, with 90 percent of employees indicating they are proud to be civil servants and over 1.7 million user responses consistently indicating average customer satisfaction levels being over 90%.
An attorney‑at‑law (non‑practising), Ms. McField-Nixon holds degrees in Communications and Law, serves as an Ex‑Officio Director of the Public Service Pensions Board and is a highly decorated leader. For leading efforts to ensure the continuity of public services during the COVID‑19 pandemic, she earned the Certificate and Badge of Honour and her team, the PoCS, earned CIPD’s People Team of the Year (Public Sector). Yet, Mrs. McField-Nixon says her most cherished accomplishment came from her peers in 2025, when she was recognised by the Cayman Islands Society for Human Resource Professionals with the Pinnacle Award for HR Leadership.
Speaker - Michael Myles
Michael Myles is a lifelong advocate for youth empowerment & community growth in the Cayman Islands. His passion for service & leadership was nurtured from a young age, culminating in a four-year football scholarship to Lindsey Wilson College, where he earned a Bachelor of Arts in Human Services.
With 35 years of experience addressing the needs of families & youth, Michael began as a Social Worker Intern at the Department of Social Services in 1992 and advanced to leadership roles, including Team Leader at the Cayman Islands Marine Institute, House Manager at Bonaventure Boys Home and At-Risk Youth Coordinator at the Ministry of Education.
His visionary approach led to impactful initiatives like the Vocational Training and job training programmes, Therapeutic & Mentoring programmes, Sports & Youth programmes, Financial Literacy programmes, Behaviour & Education Support Teams, Extended After School & Youth ACT has impacted over 4000 youth.
In 2019, Michael founded Inspire Cayman Training Limited to bridge gaps in Technical Vocational Education & Training, life skills, career development and employment placement programmes. Under his leadership, ICT has become an accredited training center, equipping over 1000 Cayman’s youth and adults for sustainable careers.
On April 30, 2025, Michael was elected to Parliament by his constituency of Prospect. On May 6, 2025, Michael was appointed as a Cabinet Minister, Ministry of Caymanian Employment & Immigration. He is responsible for Immigration and the Department of Labour and Pension.
Michael’s unwavering commitment has raised over $5 million for youth development.
Speaker - Louise Reed
Louise Reed is the Managing Director of CML and Nova Recruitment, with over 25 years of experience in human resources, talent acquisition, training, and career development. She has played a key role in the growth and diversification of the CML Group, including the launch of Nova Recruitment in 2016 and the co-founding of Connect by Nova in 2020 — a non-profit organisation focused on supporting students, job seekers, and career changers through targeted development, upskilling, and improved access to meaningful employment.
Louise holds a Bachelor’s degree in Business and Finance and has further strengthened her leadership expertise through executive programmes at Oxford University’s Saïd Business School.
She is deeply committed to advancing local employment and workforce development, with a focus on creating accessible and sustainable career pathways for Caymanians. Through Nova and Connect, she continues to champion initiatives that enhance employability and support long-term career progression within the community.
Louise has served as Chair of the Immigration Service Providers (Cayman) group since 2020, working collaboratively with industry stakeholders to support alignment on immigration processes and regulatory engagement. She is also a committed advocate for diversity and inclusion, having been a founding member of Gender Equality Cayman and serving with the CISHRP Board for six years.
Speaker - Alanna Trundle
Alanna Trundle is President of Global Captive Management Ltd., where she leads a high performing team and works with organizations to drive meaningful outcomes through innovative risk and insurance strategies. Since joining the firm in 2010, she has built a reputation for combining deep technical expertise with a people first leadership approach. A Chartered Accountant by background, Alanna began her career with Deloitte before relocating to the Cayman Islands.
Alanna is passionate about developing strong teams, empowering individuals, and fostering cultures where people can perform at their best. She is particularly interested in how leadership, communication, and trust underpin organizational success.
She has been recognized by Captive International as one of the industry’s Influential Women and named in Captive Review’s Power 50, reflecting both her professional impact and her commitment to driving positive change.
Outside of work, Alanna enjoys staying active and spending time with her three young children.
Speaker - Kim Wallace-Watler
Kim Wallace-Watler is a Clarity and Confidence Coach, speaker, and HR leader with over 20 years of experience helping individuals and organizations thrive.
As the founder of Intuitive Coaching and creator of Clarity with Kim, she works with high-achieving professionals who feel stuck, disconnected, or ready for more. Her guidance and support help clients reconnect to who they truly are and build (or redesign) a life that’s deeply satisfying and meaningful.
With a background in senior HR leadership and SHRM-SCP certification, Kim brings a rare and powerful blend of corporate credibility and real-life experience in transformations to every client interaction – and she shares these insights on every stage she steps onto.
After navigating her own personal life transition, one that brought her face-to-face with the gap between external success and internal fulfillment, she made the courageous choice to rebuild her life with intention. That journey is now the foundation of her work, fueling her passion to help others find clarity, reclaim confidence, and create lives that are not just successful, but deeply meaningful. By extension, she seeks to support organizations in their people deliverables, outputs and engagement.
Known for her relatable, honest, and practical approach, Kim delivers impactful talks on personal clarity, confidence, wellbeing, and navigating life’s transitions. She empowers audiences to stop living by default and start leading with purpose, both personally and professionally. In her ‘You…Re-imagined’ session, she flips the focus from performance back to us as individuals and all that we can become!
Speaker - Anika Jefferson
Anika is an accomplished HR professional, dynamic host, and seasoned public speaker with a passion for people, purpose, and creating unforgettable experiences. She holds a Master’s Degree in Human Resources, a Bachelor’s Degree in Globalization, an ILM Level 3 certificate, and is proudly certified as a SHRM CP. With over 11 years of experience in the HR field, she currently serves as an HR Manager specializing in Recruitment, where she blends strategy, empathy, and innovation to help organizations build strong, people centered teams.
Beyond her corporate expertise, Anika brings a unique flair to every stage she steps on. Crowned Miss Cayman Islands 2017, she has over six years of pageant experience that sharpened her poise, presence, and ability to connect with audiences of all kinds. She is a seasoned emcee, having hosted numerous company events, church functions, a wide range of HR training sessions and wellness lunch and learns and most recently, having co-hosted the annual Talent Xposition and the HR CAHRE Awards. Her warm energy, quick wit, and polished delivery make her a crowd favourite.
A creative at heart, Anika is also a singer who performs occasionally and believes in the joy of expressing oneself—especially through Disney karaoke in her downtime. Offstage, she is a devoted wife, an idea generator, and someone who finds inspiration in both structure and spontaneity.
Whether she’s leading a room of HR professionals or sparking laughter between sessions, Anika brings authenticity, professionalism, and a touch of sparkle to every moment.
Speaker - Joy Baldridge
Joy Baldridge creates cutting-edge professional learning and development programs that empower individuals and organizations to excel. Since 2015, she has partnered with 60+ corporations, organizations, and government agencies in Grand Cayman, as well as hundreds across the United States and the world.
Joy has delivered over 2,500 training, coaching and keynote presentations. Her sessions are transformational – having immediate positive impact. They are custom designed bring mind shifts, skill shifts, and lasting behavior change, so the learning directly translates into measurable workplace results.
Selected for 2x TEDx presentations and a published author, Joy is a renowned influencer on leadership, communication, stress reduction, and positive change.
She is on the 41 Top Motivational Speakers list. Her message is fresh and new.
Joy shares innovative, actionable tools that all can quickly benefit from by applying to everyday challenges at work and in life. Her first official speaking engagement was at the White House. She got there by cold calling the president.
Speaker - Gemma Henry
Gemma Henry is a strategic consultant with over 15 years’ experience supporting organisations across the UK and Cayman Islands in the areas of business development, marketing, internal communications, stakeholder engagement, and organisational culture.
Through her consultancy, four+, Gemma works closely with leadership teams to help businesses strengthen brand visibility, improve internal engagement, support growth initiatives, and navigate periods of operational and cultural change.
Her background spans professional services, financial services, technology, and the not-for-profit sector, with experience supporting leadership teams on people and culture initiatives, communication strategies, operational coordination, and employee engagement. Gemma holds a Master’s degree in International Human Resource Management and is a Chartered Strategic Marketer with the Chartered Institute of Marketing, bringing a commercially focused and people-centric perspective to workplace communication and change.
Speaker - Veresh Sita
Veresh Sita is a Fortune 500 executive turned entrepreneur, keynote speaker, and Founder and
CEO of Vasana.ai, a platform building the operating system for human performance.
Over the course of his career, Veresh has led large-scale global teams and major business,
digital, and organizational transformations across some of the world’s most recognized brands.
He previously served as Chief Information Officer at Alaska Airlines and Colliers International,
and later became Executive Vice President and Chief Digital and Innovation Officer at Avis
Budget Group, where he led global technology, digital experience, and innovation initiatives. He
has also held senior leadership roles at Starbucks Coffee Company, WeWork, Emaar, F5
Networks, and Accenture.
Throughout his leadership journey, Veresh developed a deep interest in human behavior,
leadership under pressure, team dynamics, and what enables organizations to build
high-performing teams and cultures. He has worked closely with executive leadership teams,
HR organizations, and operational leaders to help organizations navigate transformation,
growth, resilience, and change at scale.
Today, through Vasana, Veresh combines behavioral science, neuroscience, technology, and
practical leadership experience to help individuals and organizations better understand how
people think, respond, collaborate, and perform under pressure.
Born and raised in apartheid South Africa, Veresh’s personal experiences shaped his lifelong
mission to help people thrive, strengthen human connection, and build healthier, more resilient
organizations and communities.
Speaker - Dr. Kalila Bodden
Dr. Kalila Bodden is a Caymanian executive coach, medical doctor, and wellness strategist who
helps leaders, teams, and organizations improve performance, reduce burnout, and work more
effectively under pressure.
She works with senior leaders across government, healthcare, corporate, and professional
services environments to strengthen leadership effectiveness, improve accountability, reduce
organizational friction, and build healthier, more sustainable ways of working. Her work focuses
on helping leaders sustain high performance without sacrificing personal wellbeing.
Dr. Bodden has delivered hundreds of hours of executive coaching, 360° leadership feedback,
and leadership and wellness workshops across both public and private sector organizations.
She previously held a senior leadership role at one of the Cayman Islands’ largest health
insurers, where she oversaw $125 million in complex care operations across three countries
and partnered closely with executive leadership to help drive large scale wellness initiatives.
With a unique ability to bridge leadership, behavioral health, and organizational performance,
Dr. Bodden combines clinical insight with practical executive experience to help individuals and
teams navigate pressure more effectively and build sustainable high-performing cultures.
She earned her medical degree with honours from the Royal College of Surgeons in Ireland,
completed specialized training at the Mayo Clinic, and has undertaken advanced studies in
Strategic Health Planning in the United Kingdom. She also holds multiple international coaching
certifications.
Speaker - Wesley Howell
With more than 35 years of public service experience, Mr Howell has held numerous senior leadership roles across government, including previous service as the Chief Officer responsible for Home Affairs, Deputy Director of IT and more recently as Supervisor of Elections, where he successfully oversaw national general elections and referendums with a strong focus on transparency, integrity, and citizen engagement.
In his current role, Mr Howell is responsible for the coordination of key statutory functions, policy development, and administrative reform across multiple agencies, including Workforce Opportunities and Residency Cayman (WORC) and the Department of Labour and Pensions. His leadership has helped advance digitisation initiatives, streamline immigration processing, and strengthen Cayman’s border and labour frameworks to support national development and security goals.
Mr. Howell holds a Master’s in Business Administration and professional certifications in governance, policy leadership, and management. Known for his calm, solutions-focused leadership style, he passionately advocates for good governance, national security, efficient public service, and developing Caymanian talent within the civil service.