How Flexport Launched Outbound in a Traditional Industry

Flexport launched outbound in the logistics industry, where cold outreach wasn’t the norm. Here’s how they built a motion that now drives 90% of revenue.

Read time: 7 min

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Welcome to a new 🔒 subscriber-only edition 🔒 of my weekly newsletter of Outbound Kitchen. Each week, I dive into reader questions about scaling outbound and making it your #1 growth engine. For more: Live Outbound Classes | Podcast

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Flexport's ascent from a modest logistics startup to an $8 billion industry disruptor was propelled by a meticulously crafted outbound sales strategy, spearheaded by CRO Ben Braverman and operations-turned-sales leader Brian Li. This blueprint deconstructs their approach, offering actionable lessons for businesses venturing into outbound sales within complex industries.

1. Company Context at Outbound Launch

In 2014–2015, Flexport initiated its outbound sales efforts, when Ben Braverman was appointed as CRO. Operating with a sub-20-person team, the company relied heavily on founder-led sales. The logistics industry was dominated by legacy players like Kuehne + Nagel, characterized by manual processes and a lack of digital transparency. Flexport positioned itself as a technology-first logistics platform, a radical departure from traditional freight forwarders.​

Key challenges included:

• Market Skepticism: Shippers accustomed to phone/fax workflows doubted cloud-based solutions.

• Complex Decision-Making: Procurement involved multiple stakeholders across logistics, finance, and operations.

• Regulatory Hurdles: Customs compliance required navigating numerous country-specific regulations.​

Ben later admitted the team was "the most unproven sales organization in the history of companies that got this big". This underdog status fueled a culture of experimentation.

2. Outbound Impact

Flexport's outbound sales strategy delivered remarkable results:

1. Revenue Contribution: The outbound sales motion ultimately generated over 90% of Flexport's revenue.

2. Rapid Revenue Growth: The company grew from a small startup to achieving $442 million in sales by their fifth year.

3. Valuation Milestone: Flexport reached an $8 billion valuation, demonstrating extraordinary growth in a traditionally low-margin industry.

4. Industry Transformation: Beyond their business success, Flexport helped modernize logistics practices across the industry through their technology-forward approach.

3. How did Flexport launch outbound, and what lessons can you apply immediately?

Now, let's focus on what specific actions Flexport took to scale efficiently and build outbound from scratch?

In the paid edition, I break down exactly:

• The ICP frameworks they used

• Their outbound messaging examples you can copy.

• Team structures, specialized roles, and hiring strategies.

• The tech stacks they used at an early stage.

• Clear “What Worked vs What Didn’t,” with actionable takeaways.

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