Brent Pliskow

Customer Experience & Operations Executive

Support is the earliest signal a business gets. I build the teams that act on it.

20+ years leading, scaling, and transforming global service organizations across marketplace, SaaS, and enterprise environments, modernizing operations through AI, automation, and operating model redesign.

Portrait of Brent Pliskow
20+ Yrs
CX Leadership
Upwork: VP & GM, Customer Support
Prior: Samsara, Box, GE, Credit Acceptance

About

From the help desk to the leadership table.

I started on a help desk in 2002 and have spent two decades building and leading support organizations, from first-line analyst to Vice President and General Manager of Customer Support at Upwork, where I sit on the Extended Leadership Team.

What hasn’t changed is how I see support. Customers send the earliest signal that something is broken: the same question asked three different ways, the same frustration repeated across tickets, well before it shows up in a metric or drives a customer away. Organized well, support catches those patterns and feeds them back to Product and Engineering, so the company fixes the cause instead of answering the same ticket forever.

That’s the thinking behind the AI-first model I built at Upwork: not automation for its own sake, but automation that frees people to work the signal instead of the backlog. I bring the same lens to every organization I lead: fewer repeated issues, stronger trust, and service that gets better instead of just busier.

Millions
Active daily users supported across Upwork’s global marketplace
80%
Self-service adoption after an AI-first redesign of Upwork’s support model
100K+
Customers supported at Box, including 70% of the Fortune 500
20K+
Enterprise customers supported by the team I led at Samsara

Philosophy

Solve the problem. Prevent the next.

That’s a principle I helped put into words for our support organization at Box, built on an instinct I’d already been practicing since my very first job. It comes with four tenets.

Be a detective.
Understand the customer impact.
Solve for the long term.
Build foundations your peers can leverage.

Read quickly, that sounds like decent advice for an agent having a good day. Lived out, it scales from a single sharp instinct on one ticket to infrastructure an entire company leans on. At Box, I built something called the Trending Issue program before any crisis demanded it. It was a way of linking individual tickets back to a shared pattern instead of treating each one as its own isolated case. When a handful of customers quietly reported that files wouldn’t load one December, that system is what let us see it wasn’t a coincidence. What followed was weeks of tracing it back to a library update, mapping the damage, and having honest conversations with every customer affected. We caught it early because the system to see it already existed.

That’s the job, as I see it. Support is usually treated as a service function: close the ticket, move on. I think of it as an intelligence function. Every contact carries information about intent, friction, and what a customer expected but didn’t get. Customers don’t experience a company the way the company experiences itself. They don’t see the org chart, just one relationship. Captured well, that information doesn’t just close tickets faster. It changes what the business builds next.

Speaking & Media

Where the work has been seen.

2025 – PresentZendesk Customer Advisory Board Member
2024CCW: Breakout Speaker, Transforming Customer Experience with AI
2024Zendesk Relate: Panelist, WFM Reporting to Boost Agent Performance
2024Zendesk AI Summit: Panelist, Customer Panel
2020Zendesk Relate: Panelist, Optimizing and Improving Customer Analytics
2018Zendesk Relate Live: Panelist, Game-Changing Apps Built on the Zendesk Platform

Experience

Where the work has been.

Full history on LinkedIn →

Select a role to read more

Lead a global customer operations organization responsible for support, disputes, payment operations, and executive escalations across a marketplace serving millions of users worldwide. Own the service delivery strategy, operating model, and transformation agenda with emphasis on AI enablement, scalability, customer trust, and cost efficiency. Architected an AI-first operating model that eliminated most Tier 1 agent-handled interactions and drove self-service adoption to 80%, reducing contact rates by double digits year over year while sustaining strong customer satisfaction. Serve on Upwork’s Extended Leadership Team, partnering cross-functionally with Product, Engineering, and Trust & Safety to align customer operations with enterprise priorities.

Previously

Directed a 50-person global organization supporting 20,000+ enterprise customers. Served as single-threaded leader for Enterprise Support, Technical Account Management, and global incident and escalation management. Redesigned the support operating model around product specialization and implemented a stronger performance management framework, improving resolution speed, accountability, and customer satisfaction. Partnered closely with Product and Engineering to improve reliability and strengthen customer trust.

Director, Product SupportLed customer support strategy for 100,000+ customers, including 70% of the Fortune 500. Managed distributed teams across multiple U.S. hubs, leading organizational redesign, performance-based compensation structures, and improvements to self-service and strategic-account support. Played a central leadership role in crisis and incident response, coordinating cross-functional action and executive visibility during high-priority events.

Earlier role: Senior Manager, Product / Technical SupportBuilt and scaled technical support operations, overseeing product specialists and operations personnel across multiple locations. Founded a Support Operations team focused on experimentation and data-driven improvement, and helped transition the organization from a tier-based model to a collaborative, expertise-led model.

Led enterprise collaboration support operations in a large, complex corporate environment. Drove modernization of support processes through knowledge-management and workflow automation, and standardized incident response and communication practices across business units, improving visibility and executive awareness during high-impact events.

Advanced through multiple leadership roles spanning help desk operations, application support, technical supervision, and project management, including Project Manager, .NET Development/Application Support Supervisor, Help Desk Supervisor, Sr. Help Desk Analyst/Knowledge Administrator, and Help Desk Analyst. Delivered process improvements and knowledge-management initiatives that improved resolution consistency and team effectiveness.

BA, Computer Science & Judaic Studies, Hiram College. The Leadership Consortium (TLC); ITIL Foundations v3.

Let’s talk about customer experience and operations.