Strategic Guidance for Visionary Growth
We help organizations shape the future of work. From go-to-market readiness to investment decisions, we turn complexity into clarity.
About Calibogue Advisors
Calibogue Advisors is a boutique advisory firm that partners with investment banks, private equity and venture capital firms, and enterprise software companies at all stages of growth. We bring executive-level insight, operational know-how, and narrative excellence to help leaders make high-impact decisions.
Expert Advisory Services
We provide high-impact advisory in six essential areas for your business growth and success.
Expert M&A & Investment Support
Act as your insider on market, product, and tech diligence.
Executive Coaching
Navigate complexity with trusted guidance from an experienced operator.
Compelling Company Storytelling
Identify opportunities, clarify priorities, and focus product investment.
Bold Product Strategy
Shape a narrative that resonates with investors, customers, and employees.
Cut through the noise with strategic messaging that captures your edge.
Differentiated Product Positioning
Align product and go-to-market for scale and repeatability.
Product & Sales Interlock
Who We Work With
We advise high-growth companies and investment firms building what's next.
Why Calibogue
Deep enterprise in HCM and Talent Tech
Growth-stage startups
Investors evaluating B2B software opportunities
Founders leading transformation
Enterprise SaaS (HCM & Talent Tech)
Proven track record with C-suites and boards
Sharp insight, candid feedback, and clear execution
Tailored, flexible, strategic support—without the bloat
Meet Our Founder & Principal
Leighanne Levensaler is the founder & principal of Calibogue Advisors, and a seasoned operator with over 25 years of experience at the intersection of people and technology. As EVP of Corporate Strategy and SVP of Products at Workday, she helped scale the company into a global market leader, co-founded Workday Ventures, and served as Managing Director, investing in and advising high-growth enterprise software companies.
She currently serves on the boards of Guild, League, Jobcase, and Legion Technologies, and advises a range of forward-thinking organizations including Kerplunk, BetterUp, FirstUp, Beamery, Onboarded, and the SemperVirens Accelerator. Widely respected for her expertise in HR and talent technology, Leighanne is known for helping visionary teams build and scale companies shaping the future of work.
Leighanne Levensaler
Our Name
The Calibogue Sound is a tidal sound nestled between Hilton Head and Daufuskie Islands in Beaufort County, South Carolina. It's ecologically rich, visually stunning, and a key waterway for residents and visitors alike.
Calibogue (n.)
Creek Indian origin: "Deep spring" or "deep waters."
A place where clarity, renewal, and possibility rise from below the surface.
We believe that true innovation and growth emerge from depth: deep thinking, deep listening, and deep partnership.
We work with clients to surface the untapped potential within their teams, strategies, and ideas.
