About Patrick O'Sullivan
Patrick O’Sullivan is 48 and the chief revenue officer of a Series E cybersecurity software company — 520 staff, $140M in recurring revenue, and 32 enterprise sellers across three regions. He owns sales, prospecting, sales engineering, partnerships and revenue operations: 95 people through eight direct reports. Twenty-five years in enterprise selling brought him here through three large technology companies and a VP seat at a business that was acquired. He lives in Buckhead with a wife of twenty-two years and three children, and keeps a weekend place at the lake. He has hit his number nine quarters running and still wakes at three in the morning about the one he missed in 2023. The arithmetic makes him distinct: a board committed to $200M by year end while ramped seller productivity sits at $1.4M against a $1.8M target.
He optimises for the forecast and the discipline underneath it, and the stress shows — direct, fast, occasionally salty, intense in a quarterly review and warm one to one. Everything he explains arrives as a deal story. Chat is short and frequent, email is action-forward, and calls end with him summarising what was agreed. His vocabulary is the enterprise sales canon: the champion, the economic buyer, air cover, the back-channel, ramped productivity. He has no patience for a claim of tenfold anything. Two things end a conversation: a flattery cold opener, and a salesperson explaining a qualification methodology he has practised for twenty years.
He is a strong subject at consideration and decision for software sold to revenue leadership and revenue operations at growth-stage and pre-public software companies. He is exacting about productivity claims and wants numbers from named sellers over a real period rather than the warmth of a pilot. The specific integration question he asks — whether the tool writes back to the opportunity record — separates serious vendors from the rest immediately. He is precise on seat flexibility, because his seller count moves and a multi-year per-seat commitment without downward flex is a non-starter. He is explicit about routing too: he takes no cold outbound and names the two paths that work, a peer introduction or a conversation started with his operations lead. He is weak for small-business sales motions and organisations outside technology.
His media concentrates on LinkedIn, podcasts and a private peer community. LinkedIn, podcasts, connected television, direct mail and email all score high; he publishes weekly, comments daily on his sellers’ posts, and listens to a sales podcast between meetings. He lurks in a peer community of about ten revenue chiefs at similar companies, and that group, with two mentors and two former bosses, is what actually decides a purchase. The day starts at 5:30 with the gym and LinkedIn and sometimes ends with a deal-strategy call at nine. Facebook, Instagram, YouTube, search, X, out-of-home, text messages and print sit in the middle; Threads, Pinterest, Reddit and app notifications are low; TikTok and Snapchat are absent.
