Automotive Executive · Greater St. Louis, MO

Jeffrey
S. Bogaski

Revenue Strategist & Sales Leader

Results-driven executive with 20+ years building high-performance sales organizations in automotive SaaS. From Naval SAR Swimmer to SVP, Jeffrey brings military discipline, data-driven strategy, and a record of transforming teams and driving exponential revenue growth.

jbogaski@gmail.com 636-222-7714 LinkedIn Profile
Jeffrey S. Bogaski
$100M+ Revenue Led
100+ Team Members
20+ Years Industry
Three Areas of Expertise
Revenue Growth Driver

Expertise in identifying strategic opportunities, implementing innovative sales strategies, and fostering high-performance teams to consistently drive revenue growth and surpass organizational targets. Overseeing annual revenue exceeding $100MM.

Talent Engagement Champion

Skilled in cultivating a supportive and inclusive work culture, implementing effective talent development initiatives, and fostering employee engagement to maximize team potential and organizational success through comprehensive training programs.

Customer Engagement Leader

Builds lasting relationships, understands customer needs, and implements tailored strategies to enhance satisfaction and loyalty, resulting in sustained business growth and market leadership across the automotive vertical.

Career History
A Track Record of Impact
TradePending
Senior Vice President of Sales
2024 — Present
North Carolina (Remote)

Partnered with TradePending to stabilize and maximize sales output, leading talent assessment, onboarding, and training for both leaders and field sales teams. Manages Sales Operations, revenue generation, and third-party participants including Rev Gen and Agency work.

  • Introduced a "Challenger" sales approach emphasizing asking and listening skills across the entire sales organization
  • Implemented data-driven KPI indicators inspired by "Measure What Matters," driving pipeline transparency and closed deals
  • Established coaching and Performance Improvement Plans (PIPs) for all sales personnel to raise baseline performance
  • Fostered a culture prioritizing prolonged success with strategic forecasting and pipeline management discipline
Affinitiv
Chief Revenue Officer
2022 — 2024
Chicago, IL

Joined to spearhead revenue growth for a SaaS-based automotive provider, overseeing annual revenue exceeding $100MM. Built a high-performance team of 100+ with 7 direct reports, reporting directly to the CEO.

  • Achieved a record-breaking month with continuous improvement in recurring revenue month over month
  • Diagnosed low sales performance — revamped compensation scheme to reinvigorate team motivation and drive results
  • Built comprehensive training programs and introduced a dedicated account management team for existing clientele
  • Established client-centric presence at industry tradeshows and podcasts, elevating brand awareness nationally
  • Partnered with marketing and OEM teams to build solutions aligned with customer needs
Cox Automotive
Vice President of Sales
2016 — 2022
Atlanta, GA (US & Canada)

Earned upward promotion across 14 years at Cox Automotive, ultimately leading a team of 100+ with 10 direct reports. Drove remarkable sales growth across multiple years in the SaaS automotive sales division.

  • Propelled revenue growth from $75K to $350K monthly recurring revenue upon taking over as VP — a 4.7× increase
  • Consistently surpassed quarterly targets through continuous coaching and engagement with indirect teams monthly
  • Achieved Presidents Club recognition for outstanding performance in 2011, 2013, 2014, 2015, and 2016
  • Traveled extensively throughout the US and Canada mentoring, coaching, and training distributed sales teams
  • Leveraged Salesforce for efficient lead tracking and accompanied teams on client visits to ensure sales success
Cox Automotive
Sales Director → Sales Representative
2008 — 2016
Atlanta, GA

Began as a Sales Representative and earned successive promotions to Sales Director. Identified strategic opportunities internally and externally, launching novel sales strategies across US and Canadian markets.

OneCommand
Sales Leader
2006 — 2008
Cincinnati, OH

Guided a sales team of over one hundred members including ten direct reports, identifying strategic growth opportunities and evaluating key growth indicators within existing business operations.

By The Numbers
Measurable Results
$100M+
Annual Revenue Overseen
4.7×
MRR Growth at Cox Automotive
100+
Sales Team Members Led
5×
Presidents Club Awards
Presidents Club 2011
Presidents Club 2013
Presidents Club 2014
Presidents Club 2015
Presidents Club 2016

"Jeff is results-oriented, leads from the front, listens intensely, and consistently follows through on his commitments. While he places a premium on winning, he takes extraordinary care of his team and producers."

Corey R.
President & CRO, WarrCloud
Professional Development
Methodology & Expertise
Sales Methodology
Challenger Sales Challenger Leadership Miller Heiman Process Pipeline Management Sales Forecasting KPI Design Measure What Matters
Functional Expertise
Revenue Operations SaaS Automotive Talent Development Salesforce CRM OEM Relations P&L Ownership Team Restructuring Executive Leadership
LinkedIn Recommendations
What Leaders Say
"

Jeff's attitude is outstanding. He took a cadenced, day-by-day approach to build relationships and understand needs throughout the region, turning it into the top region in the nation. His can do attitude powered him through and spread to the rest of our team. Jeff never once missed a sales forecast, often working with our customers late into the night to finalize a contract.

Carl Arnold
VP, Dealer Channel · Experian
"

Jeff is a focused, sales driven person who takes ownership of his role within a company and does what is needed to get the job done. I have had the pleasure of working with him on several different occasions and he has consistently performed at a high level. I highly recommend Jeff.

Doug Dyer
President & CEO · DAC Company LLC
Military Service
United States Navy

Before entering the automotive industry, Jeffrey served in the United States Navy — an experience that instilled the discipline, leadership under pressure, and commitment to teammates that defines his executive leadership style today.

USN Veteran · Honorably Served
Role
SAR (Search & Rescue) Swimmer — one of the Navy's most physically and mentally demanding qualifications, requiring elite water rescue skills and calm decision-making under extreme conditions.
Additional Role
Engine & Fire Lead Petty Officer — responsible for engine readiness and emergency fire response, overseeing crew safety and mission continuity.
Leadership Lessons Carried Forward
Mission focus, team-first mentality, and leading from the front in high-stakes environments — values that translate directly into building winning sales organizations.