Work Preference
Summary
Overview
Work History
Education
Skills
Accomplishments
Certification
Work Availability
Software
Languages
Websites
Timeline
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Steve Bowling
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Steve Bowling

Sales
Barrington,IL

Work Preference

Job Search Status

Open to work
Desired start date: 2 weeks notice

Desired Job Title

Enterprise Account ExecutiveSales ManagerAccount ExecutiveSales Director, Business DevelopmentRegional Sales Manager

Work Type

Full Time

Location Preference

RemoteHybrid
Location: Barrington, ILChicago, IL
Open to relocation: No

Important To Me

Work from home optionHealthcare benefitsCareer advancementWork-life balance

Summary

Experienced sales professional with 10+ years of success in B2B SaaS, Enterprise Account Management, and customer growth. Proven ability to build strong client relationships, manage complex sales cycles, exceed quota, and work cross-functionally to deliver results. Skilled in consultative selling, forecasting, pipeline development, and supporting long-term customer retention and expansion.

Overview

5
5
years of post-secondary education
21
21
years of professional experience
1
1
Language

Work History

Software Sales Manager – SENTRY Fleet Maintenance Program

Lite-Check
Spokane, WA
03.2026 - Current
  • deliver sales leadership and strategic direction for Sentry, a SaaS-based fleet maintenance and diagnostics platform serving commercial, military, government, and OEM trailer fleets.
  • Spearheaded enterprise pipeline development and established structured GTM processes within HubSpot CRM while enhancing multi-stakeholder sales cycles and refining forecast accuracy.
  • Counseled executive team on target-account strategy and value-based selling techniques, bolstering engagement with enterprise prospects in operations safety compliance maintenance and diagnostics sectors.
  • Developed subscription-based SaaS model featuring multi-year (36-month) agreements, generating predictable recurring revenue and adaptable hardware financing solutions.
  • Guided sales staff in solution-selling techniques and strategies for enhancing customer retention and recurring ARR through cross-functional task ownership and renewals.
  • Created tailored PowerPoint presentations featuring detail-oriented value-add slides to illustrate ROI for C-suite and departmental stakeholders during web demonstrations.

Account Executive (AE)

Imagetec
McHenry, IL
03.2025 - 02.2026
  • Senior-level Account Executive overseeing commercial sales territory with focus on detail-oriented balance between new business development and account retention to achieve and surpass monthly and quarterly revenue targets.
  • Identified and acquired mid-market and enterprise clients through targeted cold call campaigns, upsells, and on-site presentations, driving revenue growth.
  • Developed proposals, negotiated contracts, and orchestrated implementation and onboarding with service and technical teams to ensure seamless rollout and elevated client satisfaction.
  • Collaborated cross-functionally with service operations and finance to guarantee precise deal documentation facilitating timely revenue recognition.

Sr. Enterprise Account Executive

Teletrac Navman
Chicago, IL
04.2015 - 11.2024
  • Surpassed annual ACV quota of $650K, achieving total contract value of $1.8M across enterprise accounts
  • Cultivated new enterprise logo opportunities while enhancing existing portfolios through regular cross-department presentations to c-suite stakeholders.
  • Oversaw portfolio of 100 active customers, focusing on upsells, cross-selling, and retention as primary contact for 12 months post-sale while prospecting 500 to 1,000 targets for new-logo growth.
  • Sustained one of highest closing percentages company-wide and achieved over five chairmen's club and president’s club awards.
  • Converted client feedback into product and process improvements by participating in internal kaizen and voice of customer (VOC) initiatives.
  • Developed bundled solutions with routing maintenance software and dashcam technology partners enhancing market reach in transportation logistics construction and government sectors
  • Mentored junior and senior sales team members, including BDRs, to enhance performance. Led forecasting meetings to improve accuracy in revenue predictions. Re-engineered lead qualification process to boost demo-to-close conversion rates and revenue quality.
  • Sustained one of highest closing percentages company-wide and garnered over five chairmen's club and president’s club awards.
  • Engaged in internal kaizen and voice of customer (VOC) programs to translate client feedback into product and process improvements.

Sr. National Account Executive – Closer

Fleetmatics
Arlington Heights, IL
03.2012 - 03.2015
  • Generated over $1M in annual SaaS ACV through strategic insights, consultative demos, and complex enterprise negotiations.
  • Guided six BDRs to elevate pipeline quality and accelerate velocity.
  • Delivered ROI-centric presentations boosting adoption and strengthening long-term retention.
  • Secured two AE Chairman’s Club awards for exceeding quota and ranking in top 5% nationwide.

Sales Manager

Automated Professional Marketing
Chicago, IL
01.2006 - 02.2012
  • Sourced, trained, and guided 25+ sales representatives to consistently exceed goals.
  • Formulated sales scripts, KPI systems, and coaching routines to enhance productivity and conversion rates.
  • Orchestrated t1 automated dialing operations for teams of 10 overseeing daily forecasts and reporting.
  • Implemented t1 automated dialing operations for teams of 10 while overseeing daily forecasting and reporting.

Education

High School -

John Hersey High School
Arlington Heights, IL
02.1990 - 01.1995

Certificate Completion - MEDDICC, SPIN, ACTION

Professional Sales Training

Skills

  • SaaS solutions
  • Solution selling
  • Account management
  • Contract negotiation
  • Sales Forecasting
  • Forecasting & Pipeline Integrity
  • Customer retention
  • Upsell Cross-Sell Competitive Expansion
  • CRM expertise
  • CRM: Salesforce, HubSpot, Dynamics 365, Salesloft, Outreach
  • Sales training
  • Workflow tools
  • SaaS sales
  • Negotiation expertise
  • CRM proficiency
  • Pipeline management
  • Upselling strategies
  • Competitive analysis
  • Product demonstration
  • Territory management
  • Relationship building
  • Sales projections

Accomplishments

  • Consistently exceeded sales goals, grew enterprise accounts through renewals and expansion, and earned 5+ Chairman’s Club and President’s Club awards for top-tier performance. Recognized for building strong client relationships, driving revenue, and contributing to team success.

Certification

MEDDICC, SPIN Selling, Action Selling

Work Availability

monday
tuesday
wednesday
thursday
friday
saturday
sunday
morning
afternoon
evening
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Software

Saas

Salesforce

Hubspot

Dynamics 365

Outreach

Microsoft Teams

Zoom

Languages

English
Native language

Websites

Timeline

Software Sales Manager – SENTRY Fleet Maintenance Program

Lite-Check
03.2026 - Current

Account Executive (AE)

Imagetec
03.2025 - 02.2026

Sr. Enterprise Account Executive

Teletrac Navman
04.2015 - 11.2024

Sr. National Account Executive – Closer

Fleetmatics
03.2012 - 03.2015

Sales Manager

Automated Professional Marketing
01.2006 - 02.2012

High School -

John Hersey High School
02.1990 - 01.1995

Certificate Completion - MEDDICC, SPIN, ACTION

Professional Sales Training

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