Summary
Overview
Work History
Education
Skills
Websites
Training
Timeline
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Robert Herold

Cary

Summary

Enterprise Account Executive with over $100M in SaaS bookings across 23 years, achieving a peak of $19.25M in 2021. Exceeded sales quotas for 13 consecutive years, recognized as top performer at Deque Systems for a decade. Facilitated accessibility SaaS adoption in 8 of the top 10 U.S. banks and numerous Fortune 500 companies. Skilled in negotiating multi-million-dollar contracts with C-level executives and integrating AI-powered accessibility tools into client SDLC environments.

Overview

24
24
years of professional experience

Work History

Enterprise Account Executive

Deque Systems, Inc.
Herndon
04.2013 - Current
  • Global leader in digital accessibility SaaS, providing AI-powered testing and compliance solutions used by Fortune 500 companies and top U.S. government agencies.
  • Generated over $100M in career bookings; exceeded quota 13 years consecutively.
  • Achieved $19.25M in bookings in a single peak year; recognized as #1 sales performer, 2015–2024 consecutively.
  • Led the adoption of Axe DevTools, Axe Monitor, and Axe Auditor at scale in 8 of the top 10 U.S. banks, major F500s, and federal agencies.
  • Negotiated, closed, and managed 8-figure, multi-year SaaS agreements with C-level and technical stakeholders.
  • Integrated accessibility tools into enterprise SDLC pipelines, supporting CI/CD and Agile workflows.
  • Provided executive consultation for digital accessibility strategy, risk mitigation, and compliance.
  • Mentored and developed junior and inside sales teams; established processes that improved onboarding and performance.
  • Closed and managed SaaS solutions for the world’s most influential financial institutions—including BlackRock, Vanguard, JPMorgan Chase, Bank of America, Citigroup, and Wells Fargo—alongside Fortune 100 enterprises and major federal agencies. (VA, DoD, State Department).

Senior Enterprise Account Executive

AvePoint Public Sector
Arlington
08.2010 - 04.2013
  • Sold SharePoint support platforms (data protection, migration, compliance) to enterprise and public sector clients.
  • Generated $2.2M in new sales in 2012 (175% of quota); $2M in 2010–2011 (170% of quota).
  • Ranked 4th out of 148 global sales reps in 2011.
  • Closed significant contracts with Dominion Resources, AstraZeneca, Blue Cross Blue Shield, Constellation Energy, DuPont, Coventry Healthcare.
  • Managed and mentored an inside sales team of 6.
  • Major wins included AstraZeneca ($550K), Johns Hopkins ($422K), Blue Cross Blue Shield ($350K), Coventry Healthcare ($285K).

OEM Sales Executive

LogiXML
McLean
06.2009 - 08.2010
  • Sold Business Intelligence SaaS solutions to Fortune 1000 companies and ISVs.
  • Generated $450K in SaaS sales in Q1 & Q2 2010 (75% of annual quota).
  • Achieved $710K in sales in 2009 (135% of six-month quota).
  • Top OEM sales executive in 2009.
  • Negotiated and closed contracts with ISVs including Autographics, Ascentn, Metapower.

Corporate Sales Executive

Vovici
Sterling
02.2008 - 04.2009
  • Sold SaaS enterprise feedback and survey platforms to large enterprise accounts.
  • Closed $1.44M in new sales in 2008 (120% of quota); top corporate sales rep.
  • Closed contracts with AT&T, NFL, Deloitte & Touche, Corporate Executive Board, State Department Federal Credit Union, Motley Fool.
  • Responsible for 35% of total product sales in 2008.
  • Received “Hit the Ground Running” Award and “Sales Rep of the Quarter” (Q2 2008).

Enterprise Sales Executive & Inside Sales Associate

Ensemble Chimes Global
Fairfax
01.2002 - 01.2008
  • Sold HRMS and VMS platforms to Fortune 1000 and federal clients.
  • Closed over $4.3M in revenue (2005–2007).
  • Multiple President’s Circle and Top Sales Rep awards.
  • Managed/mentored inside sales teams.

Education

BA - Psychology

Miami University of Ohio
Oxford, OH

Skills

  • Enterprise SaaS sales strategy
  • AI and accessibility solutions
  • Global account management
  • SDLC integration
  • C-suite relationship building
  • Contract negotiation and closing
  • Multi-million-dollar agreements
  • Sales team leadership

Training

  • Solution Selling Training (2008)
  • SPIN Selling Training (2004)
  • Chimes VMS Sales Engineering Certification (2007)
  • SAP Business Objects Training (2008)

Timeline

Enterprise Account Executive

Deque Systems, Inc.
04.2013 - Current

Senior Enterprise Account Executive

AvePoint Public Sector
08.2010 - 04.2013

OEM Sales Executive

LogiXML
06.2009 - 08.2010

Corporate Sales Executive

Vovici
02.2008 - 04.2009

Enterprise Sales Executive & Inside Sales Associate

Ensemble Chimes Global
01.2002 - 01.2008

BA - Psychology

Miami University of Ohio

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Robert Herold