Anthony O'Boyle
Chicago,IL
Summary
Strategic Enterprise Account Executive with a track record of leading complex, multi-stakeholder enterprise sales cycles across Fortune 500 and high-growth organizations. Experienced in executive engagement, transformational SaaS evaluations, and aligning cross-functional stakeholders around customer experience, AI-driven intelligence, operational efficiency, and modernization initiatives. Recognized for translating ambiguous business challenges into measurable commercial outcomes and building momentum in high-stakes enterprise environments.
Overview
12
12
years of professional experience
Work History
Strategic Enterprise Account Executive
Sprout Social
Chicago, IL
04.2023 - Current
- Closed $3.45M+ in enterprise new business across complex, multi-stakeholder sales cycles involving executive, procurement, legal, marketing, customer care, and IT stakeholders
- Led strategic evaluations across Fortune 500 brands and global consumer organizations focused on social intelligence, customer care, AI, and influencer marketing transformation initiatives
- Closed multiple six-figure opportunities across Fortune 50 organizations and globally recognized brands
- Built executive relationships and orchestrated evaluations involving Salesforce integrations, AI-driven intelligence workflows, and cross-functional operational alignment
Account Executive → Strategic Account Executive
Salesforce
Chicago, IL
11.2017 - 04.2023
- Closed $1.5M+ ACV in FY22 at 192% to quota; earned Peak Performers Club recognition and closed the second largest deal in the business segment ($848K ACV / $2.54M TCV)
- Ranked #2 AE in Chicago and #4 AE in Central region while serving as Team Lead and 2x MVP
- Delivered $817K+ ACV and 45% YoY territory growth managing strategic Wealth & Asset Management accounts
- Consistently promoted across SMB, Growth Business, Mid-Commercial, and Strategic segments based on performance and leadership impact
Account Executive → Senior Account Executive
Hireology
Chicago, IL
04.2014 - 11.2017
- Grew customer base from 14 to 48 companies in 10 months (342% growth)
- Closed $365K in new business at 316% YoY growth
- Set company record with 37 deals closed across 52 meetings held in a single month
Education
Bachelor of Science - Psychology
Michigan State University
East Lansing, MI05-2013
Timeline
Strategic Enterprise Account Executive
Sprout Social
04.2023 - Current
Account Executive → Strategic Account Executive
Salesforce
11.2017 - 04.2023
Account Executive → Senior Account Executive
Hireology
04.2014 - 11.2017
Bachelor of Science - Psychology
Michigan State University