Full-Time

Customer Sales Manager

Business Development

Posted on 8/18/2026

Flock Freight

Flock Freight

201-500 employees

Terminal-free, shared-truckload freight platform technology-based

Compensation Overview

$100k - $120k/yr

+ Commission + Equity package

Chicago, IL, USA

Hybrid

Hybrid work model with scheduled in-office and work-from-home days; targeting talent in the Chicagoland Area.

Category
Sales & Account Management (1)
Required Skills
Sales
Supply Chain Management
CRM
Salesforce

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Requirements
  • At least 5 years of experience in sales, business development, or revenue leadership.
  • At least 2 years of experience managing, coaching, or mentoring quota-carrying sales professionals.
  • Demonstrated success achieving or exceeding team and individual sales targets.
  • Strong understanding of pipeline management, sales forecasting, customer relationship management processes, and performance analytics.
  • Proven ability to coach prospecting, discovery, qualification, objection handling, and closing skills.
  • Experience in freight, logistics, transportation, supply chain, or another complex business-to-business sales environment.
  • Experience leading high-velocity or outbound business development teams.
Responsibilities
  • Lead the team to achieve or exceed pipeline, revenue, gross-margin, and quota targets.
  • Establish performance expectations, operating rhythms, activity standards, and accountability measures.
  • Coach Account Executives through regular one-on-one meetings, call reviews, deal strategy, role plays, and individualized development plans.
  • Monitor pipeline health, conversion rates, sales activity, forecast accuracy, and customer relationship management hygiene.
  • Develop strategies to improve prospecting effectiveness, opportunity quality, win rates, and sales-cycle efficiency.
  • Support recruiting, onboarding, ramp, certification, and ongoing development of business development Account Executives.
  • Partner with senior sales leadership, pricing, operations, marketing, and customer teams to remove execution barriers.
  • Provide accurate forecasts, performance insights, and recommendations to leadership.
  • Reinforce customer-focused, data-driven, and profitable selling practices.
  • Identify performance gaps early and implement focused improvement plans.
Desired Qualifications
  • Familiarity with Salesforce, Gong, and sales enablement platforms.
  • Experience building sales playbooks, onboarding programs, or performance-improvement plans.

Flock Freight uses a terminal-free platform called FlockDirect to move freight by combining multiple shipments into a single shared truckload, avoiding traditional transfer terminals. It routes shipments directly, leveraging patented technology to speed delivery and reduce damage, with cost savings of up to 20% compared with typical truckload shipping; revenue comes from charging for freight services. Its approach differs from competitors through the terminal-free, shared-load model and its tech-enabled optimization, which can yield larger savings on weight-heavy shipments. The goal is to make freight shipping faster, cheaper, and gentler on goods by removing unnecessary transfer points and improving efficiency.

Company Size

201-500

Company Stage

Late Stage VC

Total Funding

$572.5M

Headquarters

Encinitas, California

Founded

2015

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Simplify Jobs

Simplify's Take

What believers are saying

  • Flock Freight raised $60 million in May 2025, extending runway and signaling investor support.
  • Management updated its site in July 2026, showing active product, marketing, and customer acquisition.
  • Sustainability awards in 2025 strengthen enterprise sales with carbon-conscious shippers.

What critics are saying

  • Flock Freight cut 99 employees in 2023-2024, exposing fragile margins and cost pressure.
  • PitchBook listed debt on October 21, 2024, adding refinancing strain before the next downturn.
  • Convoy's collapse shows freight brokers die fast if pooling economics fail; Flock Freight faces identical pressure.

What makes Flock Freight unique

  • Flock Freight's patented Shared Truckload pools freight without terminals, cutting damage, delays, and fees.
  • Stone Brewing renewed Flock Freight in November 2025, citing 99% pickups and 97% deliveries.
  • STL AddOns launched in July 2025, filling empty truck space and winning Fast Company.

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Benefits

Unlimited PTO

Ownership: stock options

401k

Insurance: health, dental, vision

Commuter Benefits

Paid Parental leave

Office amenities: cold brew and kombucha on tap, intramural sports, surf club, and free lunch

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

-1%

2 year growth

-1%
GlobeNewswire
Nov 4th, 2025
You Share a Beer, We Share a Truck: Stone Brewing Partners with Flock Freight to Optimize Shipping with Shared Truckload

You share a beer, we share a truck: Stone Brewing partners with Flock Freight to optimize shipping with Shared Truckload. November 04, 2025 09:02 ET | Source: Flock Freight Share Encinitas, CA, Nov. 04, 2025 (GLOBE NEWSWIRE) - Stone Brewing, one of the nation's most iconic craft beer brands, has partnered with Flock Freight to deliver to distributors across the U.S. By leveraging Flock Freight's Shared Truckload (STL) model, Stone Brewing has achieved impactful results, including 99% on-time pickups and 97%+ on-time deliveries, all while cutting costs and reducing emissions. The "You share a beer, we share a truck" campaign dives into each stage of Stone Brewing's supply chain and where Flock Freight delivers value throughout. This partnership highlights Flock Freight's consultative approach, where the company digs deep into its customers' transportation programs to uncover opportunities to add meaningful value. For Stone Brewing, this means adding more optionality to their supply chain via Shared Truckload, all while delivering top-tier service, cost savings, and emissions reduction. "At Stone Brewing, we rely on Flock Freight to be more than just a transportation provider, they're a true partner," said Chris Langmead, VP of Supply Chain at Sapporo-Stone Brewing. "Their team works closely with us daily, analyzing data, discussing industry trends, and helping us make informed decisions to optimize our network. Their flexibility and expertise allow us to move freight across several modes in the most cost-effective way." Flock Freight's ability to reliably service thousands of Shared Truckloads, multi-stop truckloads, and full truckloads has been a game-changer for Stone Brewing. By pooling shipments together with other compatible freight in Flock's network, the STL brokerage has helped Stone save 23% on shipping costs while avoiding 195 metric tons of CO2 emissions in just one year. Stone Brewing is part of a growing group of food and beverage shippers that have turned to Flock Freight for dynamic, cost-efficient transportation solutions. These brands face unique challenges, such as varying order sizes and the need to move freight into distribution facilities while adhering to strict delivery appointments. Flock Freight's STL model offers a reliable, scalable, and secure solution that adapts to their needs as these companies grow. "Our goal is to understand the way our customers see the world so we can execute against their business requirements consistently," said Kevin McMaster, SVP of Sales and Operations at Flock Freight. "For food and beverage shippers like Stone Brewing, that means finding creative ways to add significant value, whether it's pooling shipments, optimizing multi-stop routes, or combining modes for maximum efficiency." With STL, Stone keeps truckload-level service while only paying for the space they need, backed by strict service standards and appointment-based delivery. "At the end of the day, you share a beer, and we share a truck," said Langmead. "Together, we're delivering the Stone beer you know and love, while setting a new standard for efficient transportation." About Flock Freight Flock Freight is the largest Shared Truckload (STL) freight brokerage in the U.S., transforming underutilized truckload capacity into tangible value: cost savings for shippers, increased earnings for carriers, and a smaller carbon footprint. Their AI-powered, patented pooling technology optimizes across Flock's entire customer network, combining shipments from thousands of businesses into efficient Shared Truckloads. With STL, shippers enjoy truckload-level service while only paying for the space they need. Partnering with thousands of carriers, from owner operators to enterprise fleets, Flock Freight unlocks an unmatched combination of increased earnings and operational efficiency for any size fleet. Learn more at www.flockfreight.com About Sapporo-Stone Brewing Sapporo brewed the first beer of Japan in 1876. It's now the number one selling Asian beer brand in the U.S. thanks to its best-selling Sapporo Premium. Sapporo acquired Stone Brewing in 2022 to brew all of Sapporo's beer for the U.S. market. Stone Brewing, established in 1996, pioneered the West Coast Style IPA helping to fuel the modern craft beer revolution. Its most popular beers include Stone IPA, Stone Delicious IPA and Stone Buenaveza Lager. Now one company, Sapporo-Stone Brewing is among the 15 largest breweries in the U.S. and operates production facilities in Escondido, CA and Richmond, VA plus seven Stone Brewing tap room and bistro locations. Sapporo-Stone's long list of environmental efforts includes a LEED Silver Certification, world-class water reclamation and creative uses of spent grain. To find Sapporo and Stone beers, visit find.stonebrewing.com and Sapporobeer.com/find-sapporo. For more information visit stonebrewing.com and sapporobeer.com.

Latest Nigerian News
Aug 5th, 2025
Flock Freight Raises $113.5M Funding

Flock Freight has raised $113.5 million in a funding round led by SoftBank's Vision Fund. The company offers an alternative to the traditional hub-and-spoke freight shipping system by pooling shipments headed in the same direction to utilize a single truck.

San Diego Business Journal
Jun 2nd, 2025
Flock Freight Nabs $60M in Series E

In accordance with the funding round, Dean Carlson, the head of digital asset investment with new investor Susquehanna Private Equity Investments, will join Flock Freight's board of directors.

FinSMEs
May 14th, 2025
Flock Freight Raises $60M in Series E Funding

Flock Freight raises $60M in Series E funding.

Business Insider
May 14th, 2025
Flock Freight Secures $60 Million Series E Funding to Continue Scaling Shared Truckload

Flock Freight secures $60 million Series E funding to continue scaling Shared Truckload.