Casey O'Brien

Xerox needed a single managed contact center platform across 55 countries and 17 languages, replacing a patchwork of regional vendors. At Conduit Global I owned the solution from pursuit through delivery: architecture, commercial structure, and the 78-month program that followed, leading a 30-person organization that combined solutions engineering and network engineering. The program became Conduit's anchor account and the reference that opened the rest of its enterprise pipeline.

Over five years at Conduit I led the technical sale on more than $60M in contracted revenue across three motions: outsourced BPO, hosted Avaya, and cloud CCaaS. The mix matters because each has a different buyer, a different proof burden, and a different delivery model, and the same team had to win all three.

I joined Talkdesk to build the Enterprise SE function and grew it into a team of 13 covering enterprise and regulated industries, with net-new ARR of $25M+ and roughly 60% year-over-year growth. The growth came less from hiring fast and more from changing how the team sold, which the next two items describe.

A FedRAMP pursuit against incumbents with years of federal relationships. I led the technical team through the security review, the compliance architecture, and the proof of value that made the buyer comfortable moving a regulated contact center to cloud. It became Talkdesk's proof point for banking and financial services, and the foundation of the Regulated Industries practice.

When I arrived at Talkdesk, fewer than one in five demos were preceded by real discovery; the team was showing up and presenting. I made discovery-first a standard, built the frameworks to do it consistently, and got adoption to 68%. Deals that went through discovery first closed at a materially higher rate, and that's the mechanism behind the ARR number above.

Two different companies, same approach: rebuild the technical sales process around qualification, discovery, and proof. At Conduit that took win rate from 8% to 25%. At ProcessMaker it lifted win rates by more than half and doubled average contract value, with MEDDPICC and structured discovery as the backbone.

Presales productivity is mostly about repeatability. I built onboarding, enablement, and self-serve demo assets that cut new SE ramp time by roughly a third and let AEs run first meetings without an SE, which is a big part of how enterprise cycles came in two to three months faster.

Before presales I spent 12 years at the Department of Veterans Affairs, moving from network and security engineering into enterprise solution architecture. I architected the virtualized infrastructure behind the VA's Health Information Exchange over the Nationwide Health Information Network, led 20+ engineers, and ran the vendor evaluations and proofs of concept on programs from $250K to $100M. I spent that decade as the buyer, which shaped everything about how I sell.