From Saving to Investment, with Leilani Latimer

Feeling financially successful on paper but trapped in real life can change everything. In this episode, C-suite executive and board director, Leilani Latimer, shares how unintentionally becoming house poor while living in Italy as a young adult forced her to confront anxiety, control and independence. When she sold the house, those lessons ultimately set the foundation for her to achieve a healthier, more balanced relationship with money.

Leilani is a global C-suite executive and NACD Certified Board Director who leads companies through critical inflection points. She drives growth, connects strategy to execution and builds operating models designed for scale and resilience.

Her track record spans B2B, SaaS, Marketplace, AI/ML and Enterprise Technology companies across public, PE-backed and venture-backed organizations. She has held executive roles in sales, marketing, commercial operations, product and customer success, bringing a comprehensive understanding of how these functions integrate to drive performance.

She is currently a strategic advisor to growth-stage technology companies, partnering with Founders, CEOs, VCs and PEs to shape business models, strengthen go-to-market execution and design the teams and structures required to scale. She has led early-stage companies in supply chain, retail and medtech through transformational growth, building commercial and marketing engines from startup through acquisition, delivering significant revenue growth and improved forecasting.

Leilani’s deep technology expertise includes 25 years with Sabre Inc. (NASDAQ: SABR), a global leader in travel, hospitality and transportation technology. In leadership roles spanning sales, product, marketing, strategy and sustainability across North America and Europe, key achievements include repositioning the hospitality business for IPO, developing award-winning enterprise sustainability systems and products, restructuring global product investment plans and helping build the Southern European division from inception to 15% market share.

Leilani currently serves as an Independent Board Director at Black Diamond Group (TSE: BDI), Sedex and Narratize, and as an Advisory Board Member at Fiutur and FoodMesh. Her board contributions span governance, strategic capital allocation, compensation and risk oversight. Her unique perspective on corporate risk and reputation is shaped by her expertise in sustainability, over 15 years of leadership in European markets and extensive experience across multiple industries. Based in San Francisco, she is a dual US and Italian citizen.

Leilani’s story reminds us that financial independence is not a fixed destination but an evolution. From navigating cross-border careers and complex benefits systems to rethinking what fairness means in partnership, she shows how money can either create anxiety or expand possibility. Today, her focus on teaching her children to invest early, supporting female founders and building values-aligned portfolios reflects a deeper truth: wealth is a tool for choice. The freedom to decide where you live, what you support and how you show up in the world is the ultimate return on investment.

If you are considering board service, navigating career transitions or thinking more intentionally about how and where you invest, an Aspiriant advisor can help you align your wealth with your values and design a strategy that supports both independence and impact.

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