Alessandro Mason

Critic
DISC Type : C

SWE Intern at Bluejay (YC X25)

Cleveland, Ohio, United States

Overview

Alessandro is an AI/ML researcher and student at Case Western Reserve University with a passion for entrepreneurship. He is the founder of Kairos Attendance, an attendance system used by over 800 students, and has interned as a Software Engineer at Bluejay (YC S24).

He has a keen interest in global technology ecosystems, having participated in an AI development sprint in Taiwan and built relationships with tech leaders in Silicon Valley as a Veale Snyder Fellow. He also holds a Venture Capital Foundations certification.

He developed a full-stack AI voice-to-voice sales trainer from the ground up in just four weeks.

Personality Overview

Precise

Objective Thinker

ROI Driven

They prefer to analyze logically and value objective facts over emotions.  They are quite likely to negotiate on pricing or other key terms. They like to take decisions independently and do not seek others' support often.

Topics They Care About

Applied AI Solutions
His research focuses on optimal routing for AI image generation, and he has built AI-powered tools like a voice-based sales trainer, showing a focus on practical applications.
Startup Ecosystems
As the founder of Kairos Attendance and a Veale Snyder Fellow, he actively engages with entrepreneurs and venture capitalists in Silicon Valley and beyond.
Full-Stack Development
He led the development of the full-stack system for Kairos Attendance and single-handedly built a native mobile app and backend system while working at Tenfold AI.

Media Appearances

Alessandro has no verified media appearances

Work History

10-2025
SWE Intern at Bluejay (YC X25)
1-2025
Artificial Intelligence Researcher at Case Western Reserve University
9-2024
Veale Snyder Fellow at Case Western Reserve University
10-2023
Student Technician at Case Western Reserve University
7-2024
Founder at Kairos Attendance

Education

8-2023 - 5-2027
Bachelor's degree from Case Western Reserve University
8-2020 - 5-2022
High School Diploma from UWC Robert Bosch College

More Information

Social Presence :

Prographics :

Exp : 2 Location : Cleveland, Ohio, United States Job Level : Mid-senior Designation : SWE Intern at Bluejay (YC X25)
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Insights For Selling To Alessandro

During A Call Or A Meeting

DO's

  • Be ready for penetrating questions and critical examination of your pitch
  • Keep some extra margin while sharing pricing, they are likely to negotiate later
  • Be ready to answer many clarity-seeking questions and requests for information

DONT's

  • Avoid phrases like ‘trust me’, ‘others just love’ etc.
  • Don't give superficial answers, they are easily rattled by them
  • Don’t rush them till they have clearly gotten all the necessary information

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Alessandro is

  • Proof of ROI, low pricing and objective proof points are the important factors for them.
  • Will you ever get a clear answer from Alessandro

  • They do not mind saying no if they believe that it is the right decision.

Insights For Deal Planning

    How fast (or slow) will Alessandro move?

  • They are neither the fastest nor the slowest decision makers, they are somewhere in the middle.
  • Can Alessandro take some risk or not?

  • They can bear some risk if their analysis backs the decision.

You And Alessandro

Personality Compatibility


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