Kevin Oleary

About Kevin Oleary

Senior Account Executive | Fintech | 200%+ Quota Attainment | Driving ROI Through Spend & PaymentsTop-performing Account Executive with a consistent track record of outperforming quota and winning in competitive, high-velocity sales environments across fintech and SaaS.At Block, closed Q4 2025 at 221% to quota, activating $761K in GPV, ranking #1 of 19 in cohort,#4 of 184 nationally, and #1 org-wide in KPIs and field activity. Focused on helping operators improve cash flow visibility, streamline payments, and capture more revenue across channels.At Toast, generated $393K ARR in first 6 months, setting a company ramp record and earning President’s Club (FY 2024–25). Closed $1.7M+ ARR (139% to quota) by consolidating fragmented systems into unified, ROI-driven solutions.At ADP, achieved 250% logo attainment in the mid-market, closing 15 new organizations in 11 months by implementing workforce management solutions that improved operational efficiency and cost control.At CoStar Group, ranked in the top 10% nationally for net new revenue, setting company records for meetings booked and conversion rate.Known for high-volume pipeline generation, sharp discovery tied to financial outcomes, and multi-threading deals across operators, finance leaders, and ownership. I operate with urgency, precision, and a bias toward action.Focused on helping businesses turn spend into a strategic advantage.

Experience

1. Square

   Present

Education

• Walter Johnson High School

  High School Diploma

• University of Maryland - Robert H. Smith School of Business

  Bachelor of Arts, General Busiess, Communications

• University of Maryland

  Bachelor of Arts - BA, Business Management, Communications, Spanish Minor