Carolina D'Alessandro, Ph.D

Examiner
DISC Type : cs

Chief Executive Officer at Portofino Immobiliare

San Francisco, California, United States

Overview

Carolina is the founder of AMA, an AI-powered coach designed to prevent burnout in entrepreneurs. With a PhD in AI for Healthcare and executive education from Columbia Business School, she previously excelled as the CEO of a real estate firm, closing over €50M in sales.

As a serial entrepreneur who also founded an aerospace company and two non-profits, she is passionate about founder sustainability. She developed a personal method for mental and physical wellbeing, viewing it as the most critical asset for entrepreneurial success, which became the inspiration for AMA.

Unique fact: Carolina has founded companies in fields as diverse as aerospace, real estate, and artificial intelligence.

Personality Overview

Status Quo Seeker

Process Oriented

Overcautious

They are thorough and always follow a systematic approach.  Being observant comes to them naturally. The only way to convince them is by showing them examples and ample proof.

Topics They Care About

Founder Wellbeing
Her company, AMA, is dedicated to preventing founder burnout, a mission she champions based on her personal experience as a 3x entrepreneur.
AI in Healthcare
Holds a PhD in this field, which serves as the technical foundation for her proactive AI coaching platform designed to protect founders' health.
Entrepreneurship
She has founded multiple ventures, including an aerospace company and non-profits, and targets founders from accelerators like Y Combinator with her current product.

Media Appearances

Carolina has no verified media appearances

Work History

8-2024
Chief Executive Officer at Portofino Immobiliare
9-2023 - 8-2024
Director General at Portofino Immobiliare
8-2021 - 8-2023
Executive Sales Manager at Portofino Immobiliare
9-2025
Founder at Stealth Startup
2-2025
Co-Founder at DOPE Hubs

Education

Executive Education from Columbia Business School
9-2025 - 5-2026
Master's degree from Genoa Entrepreneurship School

More Information

Social Presence :

Prographics :

Exp : 4 Location : San Francisco, California, United States Job Level : Leadership Designation : Chief Executive Officer at Portofino Immobiliare
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Insights For Selling To Carolina

During A Call Or A Meeting

DO's

  • Expect them to be slow and cautious, encourage them to ask more questions
  • Spend time addressing concerns around risk and change, they will have them even if they don't express them
  • Expect them to be vague in response to your questions, ask firmly and pointedly

DONT's

  • Don't rely on relationship building even if they act pleasantly
  • Don't push them too hard to make fast decisions, give them time
  • Avoid getting into storytelling mode, especially when they ask specific questions

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Carolina is

  • Adoption by others is very important to them, followed by confidence in ROI.
  • Will you ever get a clear answer from Carolina

  • They don’t say no often, they push out the decisions or keep going around in circles.

Insights For Deal Planning

    How fast (or slow) will Carolina move?

  • They don't like to hasten, so their speed of decision-making may be slow.
  • Can Carolina take some risk or not?

  • They have little willingness to take risks, and prefer making calculated decisions.

You And Carolina

Personality Compatibility


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