Thomas Oliver.
I close enterprise deals. I build the AI that closes them faster.
A decade closing complex enterprise deals at Fortune 500 companies. $20M+ in net-new revenue and 8× President's Club. Below you: a live view of the systems I'm building to change how enterprise sales actually gets done.
I Close Deals. I Build Systems. I Spot Gaps and Fill Them.
Over a decade in enterprise technology has taught me one thing: revenue comes from clarity. Clarity on what the buyer actually needs, where the real risk is, and how to build the internal case that gets a deal across the line. At Strategy (MicroStrategy), I applied that across 8+ years of AI and BI sales to Fortune 500 accounts, generating $20M+ in net-new revenue and earning President's Club six times. At Delinea · Fastpath, I bring that same discipline to SOX-driven enterprise accounts navigating identity governance and compliance.
Alongside the day job, I build AI systems that remove the parts of the sales cycle that eat time without generating revenue. The instinct is the same one I bring to every deal: see the inefficiency, build the solution.
AI Is a Competitive Advantage. I Use It as One.
Most salespeople talk about AI. These are systems that are live, in active development, or on the near-term roadmap. Every one of them is built around a real problem in the enterprise sales motion.
Discovery Copilot
A custom GPT built around the enterprise sales motion. Aligned to MEDDPICC and SPICE qualification frameworks. Surfaces account-level insights, generates targeted discovery questions, and prepares call briefs in seconds instead of hours.
Sales Workflow Automation
A suite of AI-powered tools that eliminate repetitive sales tasks: account research, outbound email drafting, call preparation, and CRM note generation. The goal is simple. More time in front of buyers, less time on admin.
GTM Stack Integration
A connected AI layer across Salesforce, Chorus, Outlook, and LinkedIn. Buyer signals surface automatically, no manual entry required, and nothing falls through the gap.
Deal Twin
A digital twin of an active deal. Every stakeholder, every signal, every open risk modeled as a living system, then simulated forward to surface the most likely failure mode while there's still time to fix it. Forecasting by simulation, not gut feel.
Pipeline Autopilot
An agentic layer that watches the pipeline the way a copilot watches instruments: drafts the follow-up before you remember it's due, flags the deal that went quiet, queues the next-best action for every account each morning. The rep stays in command. The agent keeps the heading.
On the Roadmap
Five systems currently in development: an Account Intelligence Brief that replaces 45 minutes of pre-call research with a single input, a Champion Enablement Kit that generates the internal business case your champion needs to sell upward, a Deal Risk Scorecard aligned to MEDDPICC that flags fatal gaps before your next stage review, an Executive Email Ghostwriter calibrated to how C-suite buyers actually read, and an Objection Response Engine trained on enterprise cybersecurity and GRC objections.
A Track Record That Speaks for Itself
Ten years of closing meaningful enterprise deals across cybersecurity, AI, business intelligence, and compliance. Consistent top performance at every stop.
Enterprise Account Manager Current
Selling GRC SaaS to SOX-driven enterprise accounts across the Northeast. Engaging directly with security, compliance, and finance leaders on identity governance, access control, audit automation, and segregation of duties. The mandate: reduce audit overhead, close control gaps, and protect the business from regulatory exposure.
Senior Enterprise Account Executive 6× President's Club
Generated $20M+ in net-new revenue selling AI and BI transformation to Fortune 500 companies across financial services, healthcare, retail, and manufacturing. Managed complex, multi-stakeholder sales cycles at the executive level. Hit 113% of quota in FY2023 and 125%+ by Q3 FY2024. Named to President's Club six times and ranked among the top performers in the country throughout the tenure.
Enterprise Account Executive, OEM 2× President's Club
Sold the JReport embedded analytics suite to finance and healthcare organizations through OEM licensing agreements. Hit 152% of quota in year one and 109% in year two. This is where deep expertise in software licensing structures, embedded integrations, and partner-led deal cycles began.
Digital Marketing Business Owner
Built and scaled a performance marketing business from scratch. Managed CPA campaigns, mastered conversion optimization, and developed a systems mindset for scalable revenue generation. The foundational chapter: build something that works without you watching it every second.
If You Have a Problem Worth Solving, Let's Talk.
Enterprise sales, AI tooling, the work I'm building, or just to compare notes. Reach out.