Brandon Dudley

Commercial & Revenue Leader — Transportation & Tech-Enabled Services

Summary

Commercial leader with 16+ years building revenue engines, scaling multi-location teams, and developing new business streams in transportation and tech-enabled services. Grew The BusBank from startup to $27M+ in annual bookings — profitably — by personally running deals, building CRM infrastructure from scratch, and constructing a team around a proven sales motion. Most recently scaled the charter division of North America's largest school bus company, leading 100+ person cross-functional teams across the U.S. and Canada. Deep operational fluency in people transportation, combined with a builder's instinct for developing revenue outside the core.

Areas of Expertise

Multi-Location Commercial Leadership
  • Scaled the charter division of First Student — North America's largest school bus company — leading 100+ person cross-functional teams across dozens of locations in the U.S. and Canada.
  • Exceeded annual revenue quota in 3 of the last 5 years; deployed CRM and marketing automation to optimize forecasting, territory performance, and workflow.
  • Full sales lifecycle ownership in a multi-location, contract-driven business: territory planning, quota setting, compensation design, and incentive programs.
Revenue Development Outside the Core
  • At BusBank, built an entirely new revenue engine from scratch — grew from early-stage to $27M+ in profitable annual bookings by creating the sales motion, digital acquisition program, and vendor marketplace that didn't exist before.
  • At First Student, drove growth across charter verticals beyond core student transportation — private events, government agencies, corporate clients.
  • Launched PPC and organic acquisition programs that cut lead costs by 20% and drove 20%+ annual traffic growth.
Contract Administration, RFPs & P&L Management
  • Operated daily inside the contract administration and RFP environment that defines people transportation — school district bids, government procurement, multi-year service agreements across the U.S. and Canada.
  • Owned P&L and full commercial operations as General Manager at Buster/BusBank; maintained 100% revenue quota through a complex platform merger and corporate transition.
  • Built and reviewed bid models and pro formas for new business proposals with finance teams to ensure competitive, financially sound RFP submissions.
Operations-Minded, Thinks Outside the Box
  • Directed contact center transformation from in-office to fully virtual — built the structure, hired into it, and held performance standards across a distributed team.
  • Implemented SugarCRM and HubSpot from zero, driving a 35% increase in net ordinary income at BusBank.
  • Operates at the intersection of sales and operations — understands what it takes to deliver the service, not just sell it.

Experience

Senior Director / Director, Outside Charter Sales & Operations Aug 2019 – Present
First Student · Chicago, IL
  • Led and scaled the charter division of North America's largest school bus service provider, operating across K-12 districts, government agencies, and private-sector clients in the U.S. and Canada.
  • Led a 100+ person cross-functional organization spanning outside sales and contact center operations across the U.S. and Canada; drove 10–20% revenue growth while navigating a complex stakeholder landscape.
  • Exceeded annual revenue quota in 3 of the last 5 years; deployed CRM and marketing automation to optimize sales workflow, forecasting, and territory performance.
  • Directed contact center transformation from in-office to fully virtual, improving operational agility and talent retention.
  • Managed contract administration and RFP processes across government, municipal, and private-sector accounts.
  • Developed and managed adjacent revenue streams beyond core student transportation, including private events, corporate clients, and government agency business.
General Manager Jul 2018 – Aug 2019
Buster (Global Charter Services / BusBank / FestDrive) · Chicago, IL
  • Owned P&L and full commercial operations for North America's largest verified charter network; maintained 100% revenue quota through a complex corporate transition and platform merger.
  • Ran territory planning, opportunity management, quota setting, and compensation design; guided technical teams through consolidation of multiple platforms into a single scalable product.
Managing Director Jan 2014 – Jun 2018
The BusBank · Greater Chicago Area
  • Built and scaled a profitable charter marketplace from an early-stage company to $27M+ in annual bookings.
  • Designed and launched full commercial infrastructure from scratch: implemented SugarCRM + HubSpot, rebuilt web architecture, and created vendor marketplace and portal systems — resulting in a 35% increase in net ordinary income.
  • Personally ran sales while building the team; scaled to 1,500+ vendor partners facilitating $100M+ in trips over the company's lifetime, including enterprise event contracts for Coachella, Burning Man, and Pemberton Music Festival (99K+ attendees).
  • Built a digital acquisition strategy that drove 20%+ annual organic traffic growth; cut lead acquisition costs by 20% through a managed PPC program.
  • Established a centralized vendor selection and purchasing framework, boosting net margins by 5%.
Marketing & Operations Director Oct 2010 – Jan 2014
The BusBank · Greater Chicago Area
  • Early operator across sales, marketing, and operations as the company found product-market fit and began scaling; laid the digital and operational groundwork that enabled Managing Director-era growth.
Sales Center Supervisor Jun 2008 – Nov 2010
The BusBank · Greater Chicago Area
  • Managed an inbound/outbound sales team of up to 40 reps; led the team through a Chapter 11 restructuring while protecting core revenue, vendor relationships, and key accounts.

Education & Certifications

Bachelor of Arts (BA), International Studies Illinois College
Salesforce Mountaineer Certification Psychological Safety: Building a Culture of Inclusion & Innovation Strategies for Building a Cohesive Team Leading Technical & Subject Matter Experts

Resume

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