Executive Assistant to CTO (Hybrid)

KnowBe4•Clearwater, FL

2d•Hybrid

About The Position

The Executive Assistant to the Chief Technology Officer (CTO) is a high-agency operator who serves as a strategic partner, gatekeeper, and force multiplier for the CTO and the broader Technology leadership team. The ideal candidate is a proactive problem solver who can take ambiguous, messy situations, organize them, and present clear plans and recommendations. Operating in a fast-paced environment, this individual will manage complex logistics, protect the CTO’s time, and handle highly sensitive information with absolute discretion. This is a hybrid role based in Tampa Bay , mirroring the CTO’s schedule with roughly 2–3 days a week in-office (primarily at the Tampa co-working space, with occasional travel to the Clearwater office). Flexibility runs both ways: when the CTO is remote, you are welcome to be remote. Some domestic travel (e.g., DC, Chicago) and the flexibility for occasional international travel are required as plans shift.

Requirements

Minimum 2 years of experience in a fast-paced environment where you owned project coordination, scheduling logistics, or operational workflows
Prior exposure to data-centric environments (such as finance, analytics, or operations tracking) where you had to manage numbers, track budgets, or interface with sensitive details.
Proficient in Smartsheet, Microsoft Office (excel, powerpoint), and Docusign/Adobe sign

Nice To Haves

Bachelor’s degree preferred, but not required.
A background in Engineering, Business, or STEM fields is a major plus—we love systems-thinkers who enjoy building order out of chaos.
Notary Public would be an added plus

Responsibilities

Actively "manage up" to protect the CTO’s time. Filter requests, push back on overcommitments, and confidently say "no" to meetings that do not align with core priorities.
Independently untangle complex or disorganized situations, creating actionable plans and recommendations without requiring hand-holding.
Act as a force multiplier not just for the CTO, but for their front-line team of approximately five direct reports—balancing micro-priorities for the CTO with macro-support for the wider team.
Partner closely with the Engineering Operations lead to align on workflow, team logistics, and the CTO’s operational style.
Handle highly sensitive, confidential materials regarding organizational design, compensation topics, board matters, and personal logistics with flawless judgment.
Manage the CTO's rapid communication flow, including inbox routing, schedule optimization, complex travel coordination, and meeting preparation.
Coordinate team-building activities and smooth cross-functional logistics across the technology sector.