The Freight Show

Jordan Strawn (Werner) on Building a $400M Brokerage and What Actually Matters in M&A

Most freight M&A deals look great on paper—but execution is where they succeed or fall apart. So what actually matters when you’re integrating teams, systems, culture, and operations while the market is turning against you?  Jordan Strawn has lived every phase of that journey. He joined Reed Transport Services in 2015 when it was a $70M Tampa-based brokerage and helped scale it to $400M before Werner acquired the business in 2022. As COO through the growth years and now Senior Vice President of Logistics at Werner, Jordan has seen the full arc firsthand: scaling the company, navigating buyer interest, managing diligence, and leading integration on the other side of the deal. In this conversation, Jordan shares what made Reed an attractive acquisition target, how they built with discipline instead of chasing growth for growth’s sake, and what it really takes to make M&A work after the deal closes.  He also breaks down the operational mindset behind successful integration, why process matters more than buzzwords, how Werner structured the business post-acquisition, and why power-only and refrigerated logistics are strategic parts of the company’s broader offering.  What you’ll learn:  - Why Reed became an attractive acquisition target: how service quality, repeatable execution, and strength in food & beverage and produce helped make the company stand out  - What actually matters in M&A: how leadership teams think through diligence, cultural fit, employee continuity, and post-close execution  - How to scale without losing focus: why Reed prioritized lane density, operational discipline, and core competencies over chasing every growth opportunity  - What changes after an acquisition: the shift from operating a private business to leading inside a public company environment  - Why process is a competitive advantage: how documented workflows, training, accountability, and tech-enabled visibility create operational consistency  - How Werner approached integration: aligning teams, structures, and systems while keeping the business moving through a difficult freight market  - The role of PowerLink and refrigerated power-only: how Werner’s trailer network creates capacity advantages and sticky carrier relationships  - How multi-modal sales structure works: why centralized account ownership supported by mode specialists can improve the customer experience  Time-stamped highlights: - (00:00) Intro: Jordan’s triathlon training, upcoming Olympic race, and Ironman commitment  - (03:53) The Reed origin story and how the company grew from its early days into a meaningful brokerage platform  - (05:25) Jordan’s transition from UPS Freight into Reed and the move from operations into sales leadership - (06:16) Scaling Reed from $70M to $400M and the philosophy behind that growth  - (06:58) The Werner acquisition and what made Reed strategically attractive  - (08:22) Why Reed’s food & beverage and produce freight complemented Werner’s existing network  - (09:43) Why process matters in both sales and operations  - (13:04) What the acquisition process felt like while still running the business day to day  - (14:48) Why there was strong buyer interest in Reed and how the team evaluated fit  - (16:16) Building for quality, not just top-line growth  - (18:45) Reed’s core competency in refrigerated truckload, food & beverage, and produce  - (24:28) Jordan’s mindset during the sale and why team continuity mattered  - (26:45) The challenge of preserving culture through M&A  - (30:30) What actually changes after the deal closes: alignment, process, and decision-making  - (32:33) How Werner structured sales and account management post-acquisition  - (36:28) PowerLink explained and why power-only matters strategically  - (42:08) Expanding into refrigerated power-only with connected reefer technology  - (43:55) The building blocks of world-class operations  - (48:15) How teams drive compliance through visibility, feedback, and execution discipline  - (51:08) What keeps Jordan up at night: constant market change and keeping teams ready to adapt Guest Jordan Strawn — Senior Vice President of Logistics, Werner Enterprises Jordan spent nearly a decade helping scale Reed Transport Services from $70M to $400M before Werner acquired the company in 2022.  He now leads Werner’s PowerLink and truckload brokerage operations, overseeing logistics teams across multiple offices and helping guide the ongoing integration of Reed into Werner’s broader logistics platform. Prior to Reed, he spent years in operations at UPS Freight, where he developed the process-driven mindset that continues to shape his leadership approach today.

Phil Shook (Crowley) on CH Robinson's Decentralized Empire to Building Modern Brokerage

How does a 3PL evolve from a collection of entrepreneurial fiefdoms competing against each other to a unified, technology-enabled powerhouse? And what does it actually take to build exceptional operations in an industry where the basics—moving freight from A to B—haven't changed, but everything around it has? Phil Shook has lived through every major transformation in modern freight. He started at Hub Group in 1994 when supply chain wasn't even a college major, joined CH Robinson in 1997 as the 40th employee in the Chicago South office (which ballooned to over 100 in just three years), and spent 23 years watching the company evolve through decentralization, the game-changing American Backhaulers acquisition, and the shift to unified operations. He led intermodal operations for years, managed railroad relationships worth hundreds of millions, and worked closely with the Backhaulers integration team—learning both the "Robinson way" and the scrappier, more tech-forward approach that would reshape the industry. After a stint in equipment leasing staying connected to carriers and railroads, he's now leading North America land transportation at Crowley, building a brokerage business from the ground up with truckload, LTL, intermodal, and dray—what he calls his "dream job" for the last chapter of his career. This conversation is a masterclass in operational excellence and industry evolution. Phil breaks down the intermodal business model most people don't understand, explains why internal competition at pre-2000 CH Robinson sometimes mattered more than external rivals, reveals how the Backhaulers acquisition transformed Robinson's culture and technology, and shares what actually creates sustainable competitive advantage in brokerage (hint: it's relationships, but not the way you think). He also gets into why JB Hunt became the intermodal king, what the railroad business model teaches you about capacity planning, and why great operations teams are built on trust and alignment, not complexity. **What you'll learn** - **The intermodal business model decoded**: How rail + truck combinations work, why anything 700+ miles and within 100 miles of a rail hub can save double-digit percentages, and why JB Hunt's 150,000 container fleet makes them the undisputed leader—plus the nuances that don't show up on spreadsheets (like 80% of volume shipping Thursday-Friday changing your entire cost structure). - **CH Robinson's cultural evolution**: How pre-2000 Robinson operated like franchises where offices competed against each other more than external rivals, why the 2000 American Backhaulers acquisition was "one of the most brilliant things the company ever did," and how Backhaulers' superior technology (the Express system) and individual-level entrepreneurialism reshaped Robinson into what it became. - **Why relationships create operational advantage**: Not the surface-level "does your daughter play soccer" stuff, but how understanding shipper nuances (like discovering a lane's volume all hits Thursday-Friday), building direct relationships with receivers (so late trucks still get unloaded without accessorials), and knowing warehouse schedules lets you solve problems before customers even know they exist. - **The railroad capacity planning challenge**: Why railroads historically struggled with unpredictable volume (not knowing if 100 or 400 containers would show up Chicago to LA), how they've shifted toward airline-style reservation systems to gain predictability, and why they're divesting container ownership to focus on their core competency of moving freight. - **What makes exceptional operations orgs**: Phil's framework—it's not rocket science, it's about building great teams of detail-oriented, results-focused people passionate about being the best, then aligning them around common goals. The 90% that goes well is table stakes; differentiation happens in how you handle the 10% of exceptions through problem-solving, communication, and cost management. - **Why 3PLs won the carve-out battle**: How the industry shifted from "we don't deal with brokers" to Fortune 100 companies deliberately allocating freight to 3PLs—because aggregating the 90%+ of carriers with fewer than 50 trucks into one relationship is more efficient than shippers chasing niche capacity themselves. - **Technology's real role in brokerage**: Where tech genuinely adds value (in-transit visibility ending the "where's my truck?" game, automating unstructured data from emails/faxes into workflows, proactive exception alerts) versus where human relationships and judgment still dominate—and why customers still want to reach a human who understands the consequences of failure. - **The intermodal identity crisis that wasn't**: How 20 years ago intermodal had PR problems, but now most freight that can go intermodal does—and if customers choose truckload pricing, it's a deliberate trade-off for cost certainty and recoverability (because when a train derails in Montana, there's zero recovery optionality). **Time-stamped highlights** - (00:00) From Enterprise Rent-A-Car interviews to Hub Group: Phil's accidental entry into logistics in 1994 when supply chain wasn't a college major - (03:00) Joining CH Robinson in 1997 as the 40th employee in Chicago South—which grew to 100+ in three years - (06:00) The decentralized Robinson model pre-2000: offices acting like franchises, GMs getting profit cuts, and internal competition mattering more than external - (09:00) Creating five regional intermodal operating centers in 2000, then centralizing in 2005 to manage railroad relationships - (12:00) The 2012 shift back to leading operations: getting hands dirty with customers and carriers again - (15:00) Working on the American Backhaulers acquisition and learning "the true brokerage aspect, not just the Robinson way" - (18:00) Intermodal 101: the rail + truck model, why 700+ mile lanes within 100 miles of rail hubs work, and double-digit savings potential - (21:00) Why JB Hunt went all-in on intermodal: Mr. Hunt's visionary BNSF partnership 30+ years ago and how Hunt's now the largest with 150K containers - (24:00) How intermodal works operationally: railroads own some containers (like TripLease), big players own their own fleets, chassis pools - (27:00) The railroad capacity planning problem: not knowing if 100 or 400 containers arrive Chicago-LA, versus airlines' reservation model - (30:00) Why railroads divested container ownership: focusing on core competency of moving freight, reducing cost complexity - (33:00) What share of domestic freight goes intermodal and why more doesn't: customers know about it but choose truckload for cost certainty - (36:00) The types of freight that work for intermodal: retail, F&B, transcontinental from Asia through West Coast, temp-controlled on expedited trains - (39:00) Chicago and Memphis as railroad epicenters where all lines converge; why you might only have one railroad option depending on geography - (42:00) The Backhaulers acquisition impact: their Express system "blew away" Robinson's tech, ultra-entrepreneurial culture at individual rep level - (45:00) The 2010s evolution toward "one team" Robinson: realizing external competition required focusing efforts outward, not fighting internally - (48:00) What creates sustainable success at CH Robinson: Dave Bozeman's turnaround from Wall Street skepticism to "darlings" with 30-40x multiples - (51:00) Building exceptional operations orgs: g...

Jonathan Drouin (WWEX) on Build-vs-Buy for AI in Freight

Most freight brokerages are drowning in AI pilots that never make it to production. The gap between a working demo and a system processing thousands of loads per week is not technical — it is organizational. It comes down to setting clear KPIs up front, running biweekly AI steering committees with full leadership visibility, and being ruthlessly honest about what is working and what is not. Jonathan Drouin has lived both sides of this equation. He started as a software developer at 19, moved his first freight load in 2012 at Bear Transportation under Michael Kaney, built and sold his own TMS company and brokerage, then joined WWEX (formerly Worldwide Express) in 2019 to lead truckload technology. Over seven years, he has helped scale the company from $2B to $5B through the GlobalTranz merger and 35+ acquisitions — migrating systems, integrating business units, and now spearheading AI deployment across the entire quote-to-cash workflow. Today, he oversees product strategy and AI initiatives for a company where freight mix is roughly 40% LTL, with the rest split between parcel and truckload, serving primarily SMB and mid-market shippers as the largest UPS reseller in North America. In this conversation, Jonathan breaks down the exact framework WWEX uses to deploy AI: how they mapped every workflow from quoting to cash, prioritized initiatives against three hard metrics — customer retention, margin growth, and cost reduction — launched a dozen AI projects in year one to stress-test the boundaries, and now run every initiative through a rigorous steering committee with predefined KPIs and public accountability. He explains why email AI and repetitive tasks deliver the fastest ROI, why they shifted from build-first to partner-first as model complexity increased, the change-management discipline that separates successful deployments from expensive experiments, and why he believes AI will chip away at exception handling far beyond today’s repetitive-task automation. What you’ll learn * The three-pillar AI prioritization framework: How WWEX evaluates every AI initiative against customer retention, margin growth, and cost reduction — and why vague goals like “quality of life improvements” do not make the cut in a private-equity-backed, results-driven culture. * Why email AI wins first: The specific reasons email-based automation like quoting and carrier communication delivers faster ROI than other channels — customers do not know AI is involved, responses are faster, and workflows are linear enough for today’s models to handle exception management effectively. * From 60 ideas to 12 deployments: The exact process WWEX used to map workflows role by role and team by team, stress-test assumptions with business leaders educated on AI capabilities, and narrow down to initiatives with clear, measurable outcomes tied to business KPIs. * Build vs. partner: the 2025 inflection point: Why Jonathan went from bullish on internal builds to heavily favoring vendor partnerships — hyper-funded vendors with MIT and Carnegie Mellon talent can deploy 5–7 engineers on your use case, technology is moving too fast to bring costs in-house, and partnering enables more experimentation at lower risk. * The AI steering committee model: How running biweekly reviews with top leadership and all business stakeholders — where every project’s KPIs are public and visible from day one — creates accountability, forces intellectual honesty, and separates projects that deliver from expensive learning experiences. * Prototype to production: the 5% to 50% problem: Why getting a functional AI demo working on 1% of use cases takes almost no time, but scaling to 50% production reliability is a months-long journey — and why most people underestimate this gap until they have shipped something real. * Repetitive tasks today, exception handling tomorrow: Jonathan’s contrarian view that AI will move upstream faster than people think — today it handles repetitive work, but as models gain more context from email history, phone transcripts, and CRM data, they will chip away at exceptions that require a person today, like invoice mismatches or missing PO numbers. * Change management as the real bottleneck: Why the biggest barrier to AI ROI is not the technology — it is cultural buy-in, setting clear outcomes up front, and having the organizational discipline to push through resistance when the destination is clear and the product works. * Why PepsiCo and other shippers built internal brokerages: The logic behind turning transportation spend into a profit center, why these initiatives often plateau after aggressive early growth, and how market downturns expose the same cash-flow and margin challenges traditional brokers face. * The non-optional AI moment for every company: Why Jonathan believes companies resisting AI adoption risk becoming the next Kodak, why “quality of life” improvements do not cut it anymore, and how WWEX’s M&A-hardened culture of rallying around big decisions enables faster, more disciplined change management than most peers. Time-stamped highlights * (00:00) From French-Canadian immigrant to software developer at 19: How Jonathan’s dad put IT books in his hands and sent him to a customer site, leading to a non-linear path from clinical software to freight brokerage at Bear Transportation under Michael Kaney in 2012. * (03:30) Early career arc: CH Robinson via Phoenix acquisition, PepsiCo’s internal brokerage, then raising venture capital to build his own TMS company and freight brokerage in 2016–2017 — using his own software to prove the efficiency thesis. * (06:45) Why PepsiCo started a freight brokerage: The executive-level logic of turning billions in transportation spend from cost center to profit center, leveraging massive private fleets and backhaul opportunities, and the typical growth-then-plateau trajectory of shipper-owned brokerages. * (09:30) The shipper-brokerage plateau pattern: Why these initiatives often stall after hitting a certain scale — the same market disadvantages as traditional brokers, cash-flow challenges when you are in the business of making product, and waning executive excitement as the model matures. * (12:00) Building vs. buying a TMS: Jonathan’s journey from building his own TMS to now making billion-dollar TMS decisions at WWEX — why stability and people/process alignment matter more than cutting-edge tech, and when building makes sense. * (15:30) WWEX structure and strategy: How the $5B company operates across three go-to-market brands — Worldwide Express, GlobalTranz, and Unishippers — splits roughly 40% LTL and 60% parcel/truckload, and serves SMB and mid-market as the largest UPS reseller in North America. * (18:00) Multi-mode sales structure: Why WWEX splits LTL/parcel reps from truckload reps — sales behavior naturally gravitates toward what reps are successful at, so specialization by mode drives better outcomes than training one rep on everything. * (20:45) Jonathan’s evolving role at WWEX: From truckload platform buildout in 2019, through GlobalTranz integration and multiple migrations, to revenue operations and AP work with LTL carriers, then shifting to AI strategy in 2024 and now overseeing product strategy with heavy focus on the agent channel. * (24:00) Mapping the AI opportunity: How WWEX went role by role, team by team, workflow by workflow to map the entire q...

Terminal Industries CPO Chris Brumett on the Hidden Cost of Yard Congestion

Freight doesn’t slow down at the dock. It slows down in the yard, at the gate, and in the messy handoff between facility ops and transportation. Chris has spent decades inside that “supply chain execution” layer, and he’s now building a modern yard operating system at Terminal Industries to remove the friction most networks have learned to tolerate. In this episode, Chris Brumett, Chief Product Officer at Terminal Industries, breaks down how warehouses actually optimize (labor travel time, staging space, dock throughput), why carrier appointment compliance is a facility survival mechanism, and how low-visibility yard operations quietly create expensive downstream inefficiency. We also dig into the technology shift powering the category, from ASNs and appointment scheduling to computer vision and AI-driven workflows that reduce gate congestion, improve trailer/chassis visibility, and tighten execution across the full facility visit. What you’ll learn * Dock-Driven Warehouse Optimization: How product velocity, storage zones (ambient vs. temp-controlled), and travel time dictate door assignments and labor planning. * ASN Visibility and Receiving Automation: Why ASNs matter, how they connect to scanning and inventory accuracy, and where “ideal state” still breaks down. * Tendered vs. Operating Carrier Validation: How load brokering creates identity ambiguity at the gate and why facilities need separation between tendered carrier, operating carrier, and cargo asset. * Appointment Windows as Labor Control: The real reason strict appointment rules exist, how staging creates dock congestion, and why facilities penalize missed windows. * Inbound Priority Logic From Outbound Demand: How facilities prioritize inbound based on outbound shortages, retail promotions, and SKU velocity, not “fairness” to carriers. * Drop Trailer Strategy and Yard Buffering: Why drop-and-hook creates slack that smooths operational variance, and when yard footprint becomes the constraint. * The Hidden ROI of Yard Execution: Why optimizing “five spotters” misses the point, and how yard inefficiency causes dock labor idle time and throughput loss. * From Point Tools to Yard Operating System: How Terminal approaches the yard as an end-to-end workflow problem, not a check-in camera or a spreadsheet replacement. * Computer Vision and AI Workflow Automation: Where CV reduces gate processing time, and how AI can automate repetitive operational steps without removing the human-in-the-loop. * Facility ROI Levers That Actually Pencil: Labor displacement/reallocation, detention and demurrage reduction, and scaling volume without scaling labor. Time-stamped highlights * (01:40) Warehouse Operations and What Facilities Optimize For * (04:44) How Warehouses Actually Optimize Labor and Inventory * (08:05) Warehouse Management Systems and Labor Efficiency * (10:17) Advanced Shipping Notices, EDI, and Inbound Visibility * (12:21) Carrier Visibility Gaps and Multi-Broker Complexity * (15:08) Appointment Scheduling and Labor Planning Mechanics * (17:28) Why Appointment Compliance Drives Facility Efficiency * (22:11) Staging Loads and Dock Congestion Tradeoffs * (23:32) Freight Prioritization Based on Product Urgency * (27:00) Retail Promotions and Inbound Acceleration * (29:49) Facility Optimization vs. Shipper-of-Choice Tradeoffs * (35:17) The Yard as the Forgotten Operational Lever * (40:28) Spotter Inefficiencies and “Asteroid Hunt” Yard Problems * (44:42) Terminal’s Yard Operating System Approach * (51:11) Customer ROI, Labor Savings, and Throughput Gains Guest Chris Brumett — Chief Product Officer, Terminal Industries Chris Brumett is the Chief Product Officer at Terminal Industries and a longtime supply chain execution operator focused on warehouse and yard technology. He has spent roughly 30 years building software that improves operational execution, with the last 15 years centered on yard management and the systems that connect facilities, assets, and transportation providers. LinkedIn: https://www.linkedin.com/in/chris-brumett-6a04201/ [https://www.linkedin.com/in/chris-brumett-6a04201/] Links & references * Terminal Industries (Company): https://terminal-industries.com [https://terminal-industries.com/] * Chris Brumett Profile (Terminal / org directory): https://theorg.com/org/terminal-industries/org-chart/chris-brumett [https://theorg.com/org/terminal-industries/org-chart/chris-brumett] * ANSI X12 856 (Advance Ship Notice / Ship Notice): https://www.stedi.com/edi/x12/transaction-set/856 [https://www.stedi.com/edi/x12/transaction-set/856] * GS1 Overview of ASN (Advance Ship Notice) Standards: https://www.gs1.org/standards/edi [https://www.gs1.org/standards/edi] * Council of Supply Chain Management Professionals (CSCMP) — Supply Chain Resources: https://cscmp.org [https://cscmp.org/] Brought to you by VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/ [https://www.vooma.com/]

Price Rite Transport President Will Kerr on How Carrier Density Drove a $10M First Year

The freight market looks very different depending on which side of the phone you sit on. Will Kerr has lived both sides deeply, first as a carrier sales operator and brokerage founder who scaled Edge Logistics to $10M in its first year and over $160M in revenue, then as a trucking executive navigating today’s broker-driven freight environment. His perspective cuts through a lot of surface-level advice by unpacking the mechanics that actually determine who gets freight covered, who absorbs risk, and where margin is really made. In this episode, William Kerr, President at Price Rite Transport and Founder and former CEO of Edge Logistics, breaks down how Edge scaled by building carrier density instead of chasing volume, what separates high-performing carrier reps from the rest, and how internal brokerage dynamics quietly decide which loads get covered and which go negative. We also dig into capacity realization risk, why “autobook” freight is the real profit center inside large brokerages, how carrier tagging and internal trust are earned, and why a disciplined, broker-centric carrier strategy can outperform direct shipper relationships in the current pricing, compliance, and payment environment. What you’ll learn * Carrier Density as a Productivity Engine: Why top carrier reps drive volume through a small bench of relationship carriers to reduce rate thrash and increase repeatability. * The 50–500 Truck Sweet Spot: How mid-size fleets unlock lane-level consistency, and why those carriers are the hardest to win and retain. * Carrier Ownership and Tagging Mechanics: How “exclusive use” works inside big brokerages, including minimum booking thresholds and time-based earning rules. * Internal Deal Selling in Split Models: Why carrier reps sell deals internally to customer reps and managers, and how that determines who gets the freight. * Minimum Fees and Loss Allocation: How carrier-side minimums are structured and why losses typically roll to the customer side when markets turn. * Capacity Realization as a Hidden Risk Lever: How booking two weeks out can turn into same-day chaos when carriers shop loads and fall off late. * Why Loads Go Negative Fast: How day-of repricing at 30–100% higher rates can flip a marginal load into a multi-hundred-dollar loss. * Autobook Freight and Tribal Knowledge: How the best reps pre-position capacity and become the default option when “easy money” freight hits the board. * Carrier Compliance in the Digital Era: Why digital footprint scoring and broker-centric reporting systems can block legitimate carriers from freight flow. * Carrier Consolidation as a Reset Button: The operational steps behind merging six carriers into one brand—dispatch, safety, systems, fleet branding, and go-to-market. Time-stamped highlights * (01:20) From CME Trading Floors to Truckload Freight * (03:10) Learning Carrier Sales Inside Echo Logistics * (05:30) Commission Changes and Talent Flight * (07:30) Launching Edge From a Trailer * (09:30) Scaling a Carrier-First Brokerage Model * (12:00) What Made Great Carrier Reps Win * (14:10) The 50–500 Truck Carrier Sweet Spot * (17:10) How Carriers Get Locked and Tagged * (19:10) Losses, Minimum Fees, and Split Models * (22:00) The Myth of “No Trucks” * (24:30) Becoming a Broker of Choice for Carriers * (27:20) Tribal Knowledge and Auto-Book Freight * (30:10) Capacity Realization Failures * (35:10) Carrier Compliance in a Digital Vetting Era * (41:30) Consolidating Fleets Into One Brand Guest William Kerr — President, Price Rite Transport William Kerr is President of Price Rite Transport and Founder and former CEO of Edge Logistics, where he built a carrier-first brokerage that scaled to enterprise volume. He brings a rare operator’s view of both brokerage carrier sales and trucking network strategy. LinkedIn: https://www.linkedin.com/in/william-kerr-92275363/ Links & references * Price Rite Transport: https://www.priceritetransport.com/ [https://www.priceritetransport.com/] * Edge Logistics: https://www.edgelogistics.com/ [https://www.edgelogistics.com/] * Echo Global Logistics: https://www.echo.com/ [https://www.echo.com/] * Traffic Tech: https://www.traffictech.com/ [https://www.traffictech.com/] * Highway: https://www.highway.com/ [https://www.highway.com/] Brought to you by VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/ [https://www.vooma.com/]