She Told Both Job Interviewers She Wanted to Be CIO. They Hired Her Anyway. Calendly's Head of IT Darlene Reina on Being Unabashedly Ambitious

Her Dad Found a Rolex and Returned It. What That Taught Her About Asking for Everything.

Her father came to the United States in 1989 with next to nothing. He found a Rolex in a locker room while working as a janitor and returned it. The owner gave him a job. He stayed 27 years. In that time, he asked his employer for a green card. They sponsored it. He asked for college tuition. They paid for his associate's and his bachelor's degree. He asked to pivot into chemistry. They made a role for it.

Darlene Reina watched all of this and had one thought: if he could ask for all of that with nothing in his pocket and no English, why was she self-editing her ambitions?

She stopped. Now she opens job interviews by telling the people who will decide whether to hire her exactly what she wants: to be CIO of an organization. She told her future boss. She told the Calendly interviewer. Both were supportive. She uses it as a filter.

Darlene is Head of IT at Calendly, and in this episode she breaks down the frameworks she's built for speaking up, pitching ideas, and asking for exactly what she wants without apology.

You'll learn:

How to know which conversations are worth inserting yourself into, and which ones to let go based on span of control, stakeholder complexity, and how badly you want the outcome. The self-interest framework: why "selfless" leads to burnout, "selfish" kills collaboration, and the middle zone of self-interest is where real buy-in happens. Why she describes senior leadership as "glorified salespeople" and what changed when she stopped clicking on the backend and started selling visions instead. The "directionally correct" approach to numbers: why giving a C-suite executive "$270K plus or minus 20%" is infinitely more persuasive than "decreased time" or a 6-decimal-point calculation that took two weeks to produce. How self-editing language like "I think the answer might be..." quietly signals low confidence, and how to hit the delete button on it. Why she tells every interviewer exactly what she wants out of her career, and how she uses their response as a filter for whether the organization is actually a place where she can grow.

About Darlene Reina: Head of IT at Calendly, Darlene has built her career at the intersection of technology leadership and organizational influence. Originally from a Venezuelan family in Rhode Island, she leads IT strategy and operations at one of the most widely used scheduling platforms in the world. She is candid, direct, and unabashedly ambitious.

Connect with Darlene on LinkedIn: https://www.linkedin.com/in/darlene-reina/