Ross Kukulinski in

Ross Kukulinski

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VP Product & Interim VP Engineering at Tailscale
📍 Greater Seattle Area, United States

Ross is a technical product leader at Tailscale, building businesses at the intersection of open source, cloud infrastructure, and developer experience. He has driven significant cloud transformations at Kong and VMware. His peers often describe him as honest, transparent, considerate, and fair. He earned his B.S. from Carnegie Mellon University.

In a blog post, Ross shared that his interest in networking began with LAN gaming parties playing Warcraft II as a child. He remains a hobbyist and tinkerer, using his companys product to connect all his personal devices, from laptops to his Apple TV and NAS.

He is the author of a training course and book titled "Introduction to CoreOS" and holds a patent for a system to measure and predict transportation demand.

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Experience
16 Years
Current Role
VP Product & Interim VP Engineering
Job Level
Senior
Location
Greater Seattle Area, United States
Personality Overview

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Communication Style
Decision Approach
Work Preference

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Priorities

Topics Ross cares about

Cloud Transformation
He led the successful transformation of Kong from on-prem software to a cloud-first platform and was a founding PM for VMware's Tanzu Mission Control.
Developer Experience
This is a core focus of his career, centered on turning complex distributed systems into products that are easy to adopt, operate, and trust.
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Career

Work history

4-2026
VP Product & Interim VP Engineering
Tailscale
1-2026
VP of Product
Tailscale
5-2024 - 12-2025
VP Product Management
Kong Inc.
1-2022 - 5-2024
Sr. Director of Product Management
Kong Inc.
5-2021 - 1-2022
Director of Product Management
VMware
In the press

Media appearances

TailscaleUp 2026: a preview of Tailscale's product updates. Featured in Tailscale Blog
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Education
2005 - 2009
B.S.
Carnegie Mellon University
2001 - 2005
High School
Buckingham Browne & Nichols
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

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