Caleb Thomas
Account Executive
Jacksonville,FL
Summary
Results-driven full-cycle SaaS Account Executive specializing in selling FinTech solutions to SMBs. Demonstrated track record of closing outbound deals, conducting tailored product demos, and providing strategic consultation to business owners and finance leaders to address AR and payment inefficiencies. Skilled in navigating complex sales cycles and fostering collaboration with underwriting, onboarding, and engineering teams to ensure customer success.
Overview
3
3
years of professional experience
15
15
years of post-secondary education
Work History
Account Executive
Bill360
Jacksonville, FL
03.2024 - 05.2025
- Closed 58 SMB deals over 14 months totaling $159M in customer revenue, including the largest ARR account in company history ($60K)
- Self-sourced 60%+ of closed deals from cold outreach; all deals originated via outbound channels (self or SDR-generated)
- Shortened average sales cycle to 14–28 days while driving 30+ day DSO reductions for clients through AR automation
- Deals ranged from $5K–$50K ARR; focused on AR modernization for QuickBooks-using SMBs
Sales Development Representative
Bill360
Jacksonville, FL
10.2023 - 02.2024
- Generated qualified meetings through cold calls, email, and LinkedIn outreach.
- Targeted accounting teams and finance execs with messaging around AR automation and embedded payments.
- Streamlined lead management process by utilizing CRM software to track interactions and maintain organized customer information.
- Increased sales leads by implementing targeted outreach strategies and personalized followups.
Account Executive
PLS Logistics Services
Jacksonville, FL
06.2023 - 10.2023
- Closed logistics deals in a high-volume freight brokerage environment.
- Negotiated pricing, managed client accounts, and exceeded monthly KPI targets.
- Boosted client satisfaction by developing and maintaining strong relationships through effective communication.
Driver Manager
Cypress Truck Lines
Jacksonville, FL
04.2022 - 06.2023
- Coordinated with 60-70 drivers to ensure on-time deliveries for key accounts including Florida East Coast Railway.
- Used persuasive communication to resolve route and capacity issues efficiently.
- Monitored compliance with DOT regulations and maintained necessary documentation for audits and inspections.
Education
Business Management -
08.2019 - 08.2020
High School Diploma - Business Management
08.2005 - 05.2019
Skills
Full-Cycle Sales
SaaS Sales
FinTech
Salesforce CRM
Cold Outreach
Demo Execution
QuickBooks Integration
Objection Handling
Contract Negotiation
Client Onboarding
Communication
Timeline
Account Executive - Bill360
03.2024 - 05.2025
Sales Development Representative - Bill360
10.2023 - 02.2024
Account Executive - PLS Logistics Services
06.2023 - 10.2023
Driver Manager - Cypress Truck Lines
04.2022 - 06.2023
Jacksonville University - Business Management,
08.2019 - 08.2020
University Christian School - High School Diploma, Business Management
08.2005 - 05.2019