Leaders Driving Hospitality Career Development Must Embrace Tech, Inclusion, and Risk
The hospitality industry is under mounting pressure to modernize to meet guest expectations for seamless, tech-driven experiences and also develop leaders who can drive that transformation. According to Rackspace Technology, only 28% of travel and hospitality companies qualify as “AI leaders”— those aligning strategy, compliance, and training with real-world deployment. Another 28% remain in a passive “wait-and-see” phase, experimenting minimally or not at all. Despite visible progress, a wide gap persists between early adopters and the rest of the industry. As technology reshapes both operations and guest expectations, hospitality career development is also evolving, demanding new leadership capabilities, inclusive practices, and an innovation-first mindset.
What will it take for hospitality leaders to fully embrace modern technology, inclusive leadership, and adaptive career paths in a rapidly shifting industry?
On this episode of The Socially Awkward Podcast, host Calvin Tilokee sits down with Melissa Maher, CEO of Pinnacle and former CMO of Expedia, for an insightful discussion on leadership in hospitality. Maher explores how digital transformation, DEI, and personal development intersect in today’s hospitality environment, drawing from her decades of experience in hotel operations, sales, and executive leadership.
Highlights from the Episode:
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Why tech adoption in hospitality remains slow, and how Maher believes AI can be used beyond cost-cutting to drive revenue and enhance guest experiences.
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The real value of diversity: How Maher integrates inclusive leadership in her coaching cohorts and why she created the Pinnacle Pay It Forward program.
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How hospitality career development is shifting in response to innovation, requiring leaders to build networks, take smart risks, and adapt to new guest and workforce expectations.
Melissa Maher is a seasoned hospitality executive with over 20 years of experience, including senior leadership roles at Expedia, where she led global marketing, strategic partnerships, and the company’s first diversity and inclusion initiatives. As CEO of Pinnacle Enterprises Group, she now empowers executives through leadership development programs focused on executive presence, personal branding, and inclusive strategy. Maher is widely recognized for her expertise in commercial negotiations, DEI, and tech-enabled hospitality innovation, having secured over $1B in hotel partnerships and guided leaders across multiple industries.
