Richard Holmes
Revenue Growth Leader | Quota Overachiever | SaaS & B2B Sales Executive
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About
Results-driven sales leader with 18+ years scaling revenue from zero to $1M+ ARR, building high-performance teams, and driving consistent quota overachievement across SaaS, enterprise, and SMB channels.
Experience
CEO - Every Market Media - Chicago, IL
(2013-02 - 2026-03)
- Closed $1M+ ARR within first 18 months; sustained $250K avg ARR growth annually over 13-year tenure
- Pioneered Sales Development program for SaaS database tool EMMQuery, expanding pipeline and market reach
- Oversaw full P&L, daily operations, and client retention strategy across a multi-year growth trajectory
Started as Account Executive, left as President - ExactData - Chicago, IL
(2009-05 - 2013-05)
- Scaled team from $40K/mo (6 reps) to $800K/mo (40+ reps) via Enterprise and SMB sales channels
- Built leadership org of 2 VPs, 6 Managers, and ~40 AEs while carrying and exceeding personal quota
- Earned President's Club recognition consistently in a player/coach capacity with full P&L ownership
Sales Development Representative - Acquirent - Evanston, IL
(2007-10 - 2009-05)
Served SaaS business Avidian, Data broker ConsumerBase, Construction Business Consultants CCN
- Executed 100+ cold calls daily, generating 10–15 qualified meetings per month for targeted ICPs
- Drove top-of-funnel pipeline growth that directly supported enterprise and mid-market sales cycles
- Built foundational outbound prospecting skills across multiple verticals in a high-velocity SDR role
Internet Sales Manager - Frei Chevrolet - Marquette, MI
(2005-05 - 2007-05)
- Ranked as dealership's top performer, consistently closing 15–20 units/month by converting internet leads into in-store purchases
Education
Bachelor's degree - Entrepreneurship - Northern Michigan University
