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 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...

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...

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/

Links & references

• Terminal Industries (Company): https://terminal-industries.com
• Chris Brumett Profile (Terminal / org directory): 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
• GS1 Overview of ASN (Advance Ship Notice) Standards: https://www.gs1.org/standards/edi
• Council of Supply Chain Management Professionals (CSCMP) — Supply Chain Resources: 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/

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/
• Edge Logistics: https://www.edgelogistics.com/
• Echo Global Logistics: https://www.echo.com/
• Traffic Tech: https://www.traffictech.com/
• Highway: 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/

In this episode, Chad walks through two rare zero-to-scale runs—helping grow Access America from an early-stage Chattanooga startup into a brokerage that reached a $675M run rate before selling to Coyote, then applying the same scalability discipline to build Reliance Partners into a specialist insurance platform for trucking and logistics. We unpack the metrics and cultural rules that made the brokerage model work at scale, plus the new risk reality for brokers today—where strategic cargo theft and fraud are reshaping underwriting, controls, and the true cost to serve.

What you’ll learn

• How to design brokerage growth that scales (not just grows): The input metrics Access America measured (talk time, calls, pipeline hygiene) and why “small” behaviors become massive leading indicators.
• How to build a competitive sales culture without breaking teamwork: The CRM rules, account ownership enforcement, and RFP adjudication process that kept teams aggressive and aligned.
• Why cradle-to-grave worked—and where hybrid structures emerged: How large enterprise accounts naturally evolved into regionalized “enterprise pods” while keeping accountability tight.
• What elite cold calling really looked like: Gatekeeper navigation, dial-by-name tactics, and the persistence that turns “years of voicemails” into a top customer.
• What a “never say no” service mindset costs—and why it pays: The $32K charter-plane shipment loss that reinforced execution as a brand advantage.
• How insurance scales differently than brokerage sales: Why insurance is often “win it all or win nothing,” and how renewals create an annuity-like book when service stays tight.
• How broker risk has shifted from catastrophic liability to high-frequency cargo losses: Why strategic theft and fraud are forcing new controls—and raising the cost of coverage.
• What underwriters actually evaluate: Vetting stack, loss history, commodities, contracts, compliance maturity, and why the pool of active underwriters is tighter than most brokers assume.
• How to reduce theft exposure: Repeat-carrier discipline, high-value protocols, anomaly detection signals, and why “one exception” often becomes the breach.
• Why 2026 feels different: The optimism case for a healthier market—if the macro picture doesn’t break.

Time-stamped highlights

• (01:05) Early Access America Origins
• (02:40) Entering Brokerage as a Young Seller
• (03:33) Rising Through the Ranks
• (05:25) What Actually Scales a Brokerage
• (06:19) Metrics, Measurement, and Process Discipline
• (08:24) Competitive Culture at Access America
• (10:12) Sales Training and Battle-Tested Reps
• (11:16) Cold Calling That Works
• (16:01) Competition Without Breaking Teamwork
• (18:08) CRM Discipline and Account Ownership
• (20:05) Cradle-to-Grave vs. Chicago Model
• (25:29) Transitioning Through the Coyote Merger
• (27:05) Building Reliance Partners
• (32:00) Why Transportation Insurance Is Fragmented
• (42:35) Rising Risk and Changing Insurance Requirements

Guest

Chad Eichelberger — President, Reliance Partners
Chad Eichelberger is President of Reliance Partners, the largest standalone insurance agency dedicated exclusively to the transportation and logistics industry, insuring more trucking fleets in the U.S. than any other agency. Previously, he served as President of Access America Transport through its merger with Coyote Logistics, bringing deep experience in scaling freight brokerages, building high-performance sales organizations, and managing risk at enterprise scale.

LinkedIn: https://www.linkedin.com/in/chadeichelberger/

Links & references

• Reliance Partners: https://reliancepartners.com/
• Access America Transport + Coyote deal coverage (growth + transaction context): https://www.chattanoogan.com/2014/11/17/288154/Coyote-Logistics-Merging-With.aspx
• UPS acquisition of Coyote Logistics: https://www.ups.com/assets/resources/media/en_US/20150812_UPS_Coyote_Deal_Deck.pdf
• C.H. Robinson Worldwide, Inc. v. Miller (No. 20-1425): https://www.supremecourt.gov/docket/docketfiles/html/public/20-1425.html

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/

This episode pulls back the curtain on how a large enterprise shipper actually runs transportation procurement. Paul Estrada has spent nearly two decades leading procurement at scale, and he breaks down what most providers miss: the internal “cost vs. service” tug-of-war, why procurement lives on a scoreboard, how routing guides stay intact when markets swing, and what it really means to be a low-cost-to-serve partner. We get into radical data transparency, carrier enablement, index-based pricing, and why the best providers don’t just quote lanes—they explain the math behind sustainable pricing.

What you’ll learn

• How enterprise supply chains are actually organized: Why procurement, operations, manufacturing, and customer teams optimize for different goals—and how those tensions are managed.
• The two metrics that matter more than all others: Getting product where it’s needed, when it’s needed, at the lowest sustainable cost.
• Why procurement lives on a scoreboard: How performance is measured in dollars and cents—and why market cycles can make teams look like heroes or villains overnight.
• How enterprise shippers manage cost volatility: Dedicated capacity, portfolio mix, and risk mitigation as insurance—not ideology.
• Why carrier-agnostic procurement wins: How decisions are made across brokers, asset carriers, and dedicated fleets based on utilization and economics—not labels.
• What shippers actually look for in brokers: Sustainable pricing, operational intelligence, and the ability to explain how rates work—not just what they are.
• Why deep data sharing creates better pricing: How transparency around volumes, seasonality, and operating constraints leads to routing guides that hold up.
• How carriers are onboarded like employees: SOPs, portals, escalation paths, and training as a way to reduce churn and execution risk.
• The “Goldilocks” provider strategy: Why fewer, deeper relationships outperform wide, fragmented networks over time.
• How AI matters to shippers (and how it doesn’t): Why buzzwords don’t win business—but lower transaction costs do.

Time-stamped highlights

• (00:00) Paul Estrada and the Enterprise Shipper Lens
• (01:12) Breaking into Supply Chain and Procurement
• (02:42) Inside a Large Enterprise Logistics Organization
• (05:19) The Two KPIs That Everything Rolls Up To
• (06:40) Cost vs. Service and Internal Tension
• (08:52) The Operations Team as the Balancing Layer
• (10:16) Promotions, Firings, and the Procurement Scoreboard
• (12:27) Managing Risk and Volatility Across Cycles
• (14:46) Service Performance and Failure Points
• (16:31) Data Infrastructure and Fast Decision-Making
• (18:19) Optimization as a Cultural Advantage
• (20:45) Portfolio Thinking Across Carriers and Brokers
• (22:51) Brokers in Contractual Freight
• (24:18) Evaluating Provider Sustainability and Risk
• (25:54) Radical Data Sharing and Pricing Stability
• (30:08) Building a High-Quality Carrier Bench
• (33:47) What Separates Long-Term A-Player Providers
• (37:04) Becoming a True Shipper of Choice
• (40:21) Reading the Market and Rate Cycles
• (43:48) Index-Based Pricing and Trust-Based Partnerships

Guest

Paul Estrada — Director of Procurement, Niagara Bottling
Paul Estrada has spent nearly 20 years in transportation and supply chain leadership, with deep experience across operations and procurement at enterprise scale. He leads procurement strategy focused on cost optimization, service reliability, risk management, and long-term carrier partnerships—bringing a data-driven, relationship-oriented approach to one of the most complex logistics networks in the industry.

LinkedIn: https://www.linkedin.com/in/paulmestrada/

Links & references

• Niagara Bottling: One of the largest beverage manufacturers in the U.S. with a highly optimized supply chain — https://www.niagarawater.com/
• Dedicated vs. One-Way vs. Brokered Freight Models: Portfolio approaches to capacity and risk management
• Index-Based Freight Pricing: Contract structures tied to market indices

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/

In this episode, Ryan Keepman shares how Evans — one of the rare family-owned brokerages still standing from the deregulation era — evolved from a Wisconsin brokerage built on relationships into a multi-division logistics operator supporting everything from envelopes to excavators. We unpack the real mechanics behind service-line expansion, why the “jack of all trades” strategy kills trust, and how Evans uses intentional culture and in-person connection to keep remote teams aligned as the company scales.

What you’ll learn

• How Evans Transportation survived deregulation and stayed family-owned: Why relationship-driven brokerage and early operational investments helped Evans outlast consolidation.
• The real reason Evans diversified into multiple divisions: Diversification wasn’t a growth gimmick—it was a strategic defense after losing top clients and recognizing weaknesses in truckload execution.
• Truckload procurement vs. traditional brokerage: How Evans built a carrier procurement engine designed to protect managed transportation performance rather than operate as a pure sales brokerage.
• The modern 3PL approach and blind bidding: How Evans structures managed transportation so shippers can keep multiple brokers in the mix while Evans competes fairly without undercutting.
• How managed transportation adoption has changed: Why most shippers are already using 3PLs, how the sales cycle has shifted to CFOs and VPs, and why strategic sponsorship matters.
• Why Evans avoids price wars and “broker poker freight”: Their focus on value, complexity, and long-term trust instead of transactional spot quoting.
• How to build trust by saying no: Why Evans intentionally accepted only 3 of 13 specialized moves to avoid failure and earn long-term credibility.
• The blueprint for launching new service lines: Why face-to-face time, slowing down, and releveling teams matters more than speed when integrating new divisions.
• Evans’ culture operating system: Quarterly in-person rhythms, shared experiences, and a “do life together” philosophy that fuels cohesion across remote leadership.
• AI as a relationship accelerator: How automation reduces noise so brokers can invest in carriers, deepen relationships, and drive better outcomes.

Time-stamped highlights

• (00:00) Introduction to Ryan Keepman and Evans Transportation
• (01:14) The Early Years and Founding Story
• (03:48) Starting Evans with High Risk and Early Challenges
• (07:32) Evolution from Brokerage to Managed Transportation
• (08:16) Early TMS Development and Technology Advantage
• (09:19) Leadership Transition to Ryan
• (10:02) Diversification Strategy and the Truckload Division
• (11:07) Expansion into Mexico, Specialized, Parcel, and Government
• (13:09) Managed Transportation and Truckload Procurement
• (16:28) Modern 3PL Model and Blind Bidding
• (19:55) Shipper Trends and Managed Transportation Adoption
• (24:35) Building a Moat with Parcel and Full-Suite Solutions
• (25:46) New Warehouse Product and Strategic Fit
• (28:28) Avoiding Price Wars and Competing on Complexity
• (32:00) Building Trust Through Gradual Growth and Saying No
• (35:08) Lessons Learned in Launching New Service Lines
• (40:08) Evans Culture and the “Do Life Together” Approach
• (44:16) Leading Distributed Teams with Quarterly In-Person Rhythms
• (48:10) Leadership Growth, Directness, and Personal Reflection

Guest

Ryan Keepman — CEO, Evans Transportation
Ryan Keepman has spent 19+ years at Evans Transportation Services, building his career across key accounts, sales leadership, and executive leadership roles. He became CEO in December 2020 after serving as President (2018–2020) and previously leading growth as Vice President of Logistics Sales (2014–2020) and Vice President of Key Accounts (2007–2020). Under his leadership, Evans has evolved into a diversified logistics partner spanning managed transportation, truckload procurement, Mexico, specialized solutions, parcel, government services, and new warehousing offerings—while maintaining a people-first culture built on trust, accountability, and shared experience.
LinkedIn: https://www.linkedin.com/in/ryan-keepman-75246610/

Links & references

• Evans Transportation: Family-owned logistics provider offering managed transportation and multimodal solutions — https://www.evanstrans.com/
• Strength to Strength (Arthur C. Brooks): A framework for reinvention and sustaining fulfillment through midlife transitions
• Transportation Deregulation (Motor Carrier Act of 1980): The policy shift that reshaped the freight brokerage industry

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/

In this episode, Jeff breaks down what really makes brokerages scale (and where common models break), why most “digital transformation” initiatives stall, and how Fura’s acquisition strategy targets underperforming brokerages and gets them from manual to digital in a matter of months. We dig into the trust-building required to integrate teams, how to decide whether to build vs buy software, and why AI can shrink the adoption gap by running “in parallel” with people — not forcing everyone to change overnight.

What you’ll learn

• How freight brokerages actually scale: Why TQL “played the percentages,” built a culture engine, and used hiring + activity math to compound growth.
• Cradle-to-grave vs team-based brokerage models: What breaks in the classic spin-out approach, and how MegaCorp kept teams intact to protect continuity and service.
• Why most digital transformations fail: The real blocker isn’t software — it’s behavior change, incentives, and lack of discovery/business-case selling.
• Fura’s M&A thesis in a down cycle: The three seller buckets, why “losing money or break-even” firms can be ideal, and how Fura modernizes fast.
• How to integrate culture without breaking it: The “earn trust” approach — engagement loops, surveys, all-hands, and executive sponsorship.
• Build vs buy decision-making: The matrix Fura uses (speed, business case, differentiation/IP) to decide what to own vs partner for.
• Network-based selling in freight: How Fura maps nodes (vendors/customers/suppliers), uses proof of impact, and links sales + ops to drive adoption.
• AI as an adoption accelerator: Why AI can run in parallel with people to reduce friction — and how that reshapes brokerage into a more strategic model.

Time-stamped highlights

• (00:00) Tech Adoption and the Manual-to-Digital Gap
• (01:00) Jeff Dangelo’s Freight and Tech Background
• (04:00) Early TQL and Boiler Room Culture
• (07:00) TQL’s Hiring and Scaling Engine
• (10:00) Data-Driven Growth and Hurricane Interns
• (14:00) The Cradle-to-Grave Churn Problem
• (18:00) MegaCorp’s Team-Based Fix
• (23:00) Selling Freight vs Selling Software
• (28:00) Turvo and the Adoption Challenge
• (33:00) Fura’s Consolidation Strategy
• (37:00) The Three Seller Buckets
• (41:00) Structuring Turnaround Deals
• (45:00) The Integration Trust Playbook
• (48:30) Standardizing Systems at Scale
• (50:30) Build vs Buy Decisions
• (51:30) The Future of Brokerage With AI
• (52:04) Closing Thoughts on Execution Over Vision

Guest
Jeff Dangelo — Co-Founder and CEO, Fura
Jeff is a freight industry veteran with 20+ years across brokerage, technology, and M&A. He helped scale TQL and MegaCorp Logistics, founded Turvo, and now leads Fura, where the team acquires and modernizes brokerages by combining automation, execution, and disciplined integration.
LinkedIn: https://www.linkedin.com/in/jeff-dangelo-8a7107a/

Links & references

• Fura: Brokerage + modernization platform focused on acquiring and digitizing underperforming brokerages — https://fura.com/
• Turvo: Freight collaboration platform Jeff founded focused on shared workflows across shippers, brokers, and carriers — https://turvo.com/
• TQL: High-output brokerage known for systems-driven hiring, training, and culture — https://www.tql.com/
• MegaCorp Logistics: Brokerage scaled with a more team-based operating model and continuity focus — https://www.megacorplogistics.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/

Bill has sat in almost every important seat in modern freight: early at Coyote, co-founder of Uber Freight, Head of Trucking at Flexport, part of the Convoy story, and now leading carrier products and strategy as EVP of Convoy Platform at DAT. He breaks down why each “epoch” of freight tech took a decade to matter, why pure-play digital brokers hit a ceiling, what the DAT + Convoy combo unlocks, and how AI, AVs, and scheduling will reshape the next 10–20 years.

What you’ll learn

• The real tech epochs in freight: From post-deregulation brokerage and the American Backhaulers / CH Robinson split, to broker TMS, to “Uber for freight,” to today’s AI and automation wave.
• Why “digital freight matching” stalled as a standalone model: The hard TAM limits of being “product pure,” and why the biggest brokers will build, while everyone else partners.
• Chicago vs cradle-to-grave brokerage models: How floor design, org structure, and TMS shape service, density, and which shippers you can actually win.
• Fragmentation, scale, and the future of brokers: Why tech makes midsize brokers more dangerous, why service still wins with SMB shippers, and why you shouldn’t bet on a winner-take-all market.
• AI’s real role in brokerage and dispatch: Where AI and “AI dispatchers” add value, where they just create more work, and why channel choice (app, TMS, email, phone) really matters.
• Autonomous trucks and carrier consolidation: How AVs could change capital requirements, operating models, and what a “carrier” even is – plus how brokers and 4PLs might evolve around them.
• Why scheduling is the final frontier: How appointment setting, facilities, and dock operations quietly cap automation – and why solving scheduling unlocks the next big efficiency leap.

Time-stamped highlights

• (00:00) Bill’s background across Coyote, Uber Freight, Flexport, Convoy, and DAT
• (05:00) Post-deregulation brokerage 101: CH Robinson vs American Backhaulers and the birth of the Chicago model
• (11:00) Building Coyote’s broker TMS and why V1 tech focused inside the four walls of the brokerage
• (16:00) Uber launches, “Uber for freight” is born, and why early apps were just mobile load boards
• (22:00) Convoy, Transfix, Uber Freight and the true end-to-end “app-first” operating model
• (27:00) Why pure digital brokers ran into TAM limits and why only the largest players can justify full-stack builds
• (33:00) What shippers actually care about: why transportation is often priority #5, not #1, in the C-suite
• (39:00) SMB vs enterprise shippers: how Landstar-type agents win locals while big RFPs reward scale and data
• (45:00) Fragmentation, minimum efficient scale, and whether broker consolidation really happens
• (51:00) AI in the wild: AI dispatchers, robocalls, and why every extra medium (phone, email, portal) is a process defect
• (57:00) How apps, TMS integrations, and “one-click” workflows beat phone calls for both carriers and brokers
• (1:02:00) AVs and the carrier of the future: capital intensity, new operator models, and deterministic dispatch
• (1:10:00) 4PLs and managed transportation in an AI/AV world: why the role changes but doesn’t disappear
• (1:16:00) Inside the DAT + Convoy + Truckers Tools + Outgo stack: what Bill’s building for carriers and brokers now
• (1:22:00) Scheduling as the under-loved bottleneck: why docks, facilities, and appointments still block automation

Guest

Bill Driegert — EVP of Convoy Platform, DAT Freight & Analytics
Bill has been at the center of nearly every major freight-tech wave of the past 15 years. He was an early employee at Coyote Logistics, co-founded Uber Freight, led trucking at Flexport, and now guides carrier strategy and product at DAT following the acquisition of Convoy’s technology.
LinkedIn: https://www.linkedin.com/in/driegert/

Links & references

• DAT Freight & Analytics: Load boards, rates, and network intelligence for brokers, carriers, and shippers — https://www.dat.com/
• Convoy (acquired technology by DAT): Background on the digital brokerage and platform Bill helped integrate
• Uber Freight: Digital brokerage and 4PL / managed transportation offering — https://www.uberfreight.com/
• Coyote Logistics: Large brokerage built on the “Chicago model” Bill joined as an early employee

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/

Doug takes us through the real strategy behind Echo’s rise: building lane density the hard way, turning small acquisitions into consistent growth engines, and developing a managed transportation model with 96%+ renewal rates — all while embracing technology and AI as the next leap forward for brokerage productivity. (echo.com)

If you care about where brokerage is actually headed (AI, managed trans, multimodal, PE ownership) and what separates durable platforms from the next roll-up casualty, this is a masterclass.

What you’ll learn

• From tariffs to true competition: How deregulation shattered ICC pricing, wiped out legacy LTL players, and forced the industry to learn real pricing strategy for the first time.
• The birth of modern brokerage: Why asset-light truckload brokerage emerged only after deregulation—and how innovators like American Backhaulers reshaped the market around backhauls and empty miles.
• Echo’s real origin story: How Echo began as an outsourced transportation department for enterprise shippers before evolving into a tech-enabled, multimodal 3PL spanning managed trans, LTL, TL, partials, and intermodal.
• Why density is destiny in truckload: The hard-won journey from “calling around for rates” to building lane density and database pricing—and how acquiring Command doubled scale overnight and unlocked true competitiveness.
• The M&A playbook that actually works: Culture-first integration, treating founders like entrepreneurs, when to rebrand vs preserve identity, and how Echo consistently doubled/tripled acquired revenue by giving teams more modes and better tech.
• Managed transportation as a moat: How Echo embeds teams inside customers, integrates TMS-to-ERP, runs QBRs, and achieves ~96% renewal rates—creating long-term, high-stickiness relationships.
• AI as the next step-change in freight: Why AI is a task killer, not a job killer; how workflows happening 600,000 times a month get automated; and why adoption, incentives, and change management matter more than the model itself.

Time-stamped highlights

• (00:00) From three-martini lunches to deregulation shock and Doug’s early LTL years.
• (07:45) Deregulation fallout: bankruptcies, unions, and the rise of non-union carriers.
• (13:20) The tech turn: optimization, math, and the shift to data-driven networks.
• (18:40) The dawn of brokerage and how American Backhaulers changed the game.
• (23:30) Echo’s unexpected start as an outsourced transportation department.
• (29:10) Convincing LTL carriers to work with a broker—when most hated brokers.
• (34:55) Bootstrapping truckload: Echo’s early struggles and the path to $600M TL revenue.
• (39:30) The Command acquisition and unlocking the density flywheel.
• (43:50) Echo’s M&A playbook: talent, tech, and multimodal upsell.
• (49:20) Why Echo trains reps to sell both LTL and TL—and the payoff in share of wallet.
• (54:10) Inside managed transportation: design, integration, QBRs, and 96% renewals.
• (1:01:40) Public vs. private: life on the earnings treadmill and going private with TJC.
• (1:08:15) AI’s real impact: automating 600,000 tasks/month and freeing real capacity.
• (1:15:00) What makes automation stick: adoption, incentives, and change management.
• (1:20:00) Playing the long game: culture, trust, and the tech that truly endures.

Guest

Doug Waggoner — Chairman & Chief Executive Officer, Echo Global Logistics
Doug has led Echo through one of the most transformative runs in modern freight—guiding the company from its early days as an outsourced transportation startup through an IPO, 30+ acquisitions, the expansion into a multimodal 3PL, and ultimately a take-private deal. Under his leadership, Echo has become one of North America’s largest tech-enabled brokerages and managed transportation providers.

LinkedIn: https://www.linkedin.com/in/dougwaggoner/

Links & references

• Echo Global Logistics — tech-enabled multimodal 3PL and managed transportation provider: https://www.echo.com/
• Echo Global Logistics CEO Bio (Doug Waggoner) — official profile and background: Echo CEO page (echo.com)
• Article: Catching up with Doug Waggoner, CEO Echo Global Logistics — on freight conditions, capacity, M&A, and tech. (Logistics Management)
• Press: Echo Global Logistics CEO Doug Waggoner named a Notable Leader in Sustainability by Crain’s Chicago Business — recent recognition and sustainability highlights. (PR Newswire)

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/

We cover market conditions (soft but stable demand, high primary acceptance), the return of annual/biannual RFPs, the 50–250 truck carrier sweet spot, and how top carrier reps are now managing 100+ loads/day thanks to automation and stickier relationships. (FreightWaves)

Key Topics & Takeaways

• Market pulse (Q4 2025): Soft/stable demand; high primary acceptance; spot used surgically on low-volume lanes. Supply (driver count) is the lever to watch.
• Regulatory watch: DOT’s non-domiciled CDL rule could trim capacity; lawsuits argue lack of safety evidence. Monitor for ripple effects into 2026.
• Why shippers are consolidating now: Post-boom networks ballooned; with stability, shippers are pruning partners and going deeper with high-service providers.
• Contracting cadence: After a run of quarterly RFPs (2022–2024), many are shifting back to annual/biannual cycles to enable consistent capacity and service.
• Ops evolution: From 2005’s faxed rate sheets and no real-time visibility to today’s app/portal tracking and exception-led management.
• Productivity lift: Top reps doing 100+ loads/day is now possible via automation, sticky relationships, and inbound digital offers.
• Programs that create stability:
  • Continuous Movement: Dedicated-like weekly revenue commitments with per-mile tiers; lowers driver churn and guarantees capacity.
  • Drop Trailers: Flex for warehouse teams, fewer live-load constraints, scalable capacity; Echo is expanding via partners like Wabash TaaS.
• Tech stance: Meet carriers where they are—apps, portals, and email (still the dominant medium). Expect agentic AI to automate email-based offers and booking.
• Carrier segmentation sweet spot: Echo works all sizes, but the 50–250 truck range often yields the best strategic depth and share of capacity.

Guest

Jay Gustafson — EVP of Brokerage Operations
Company: Echo Global Logistics (https://www.echo.com/)
LinkedIn: https://www.linkedin.com/in/jaygustafson/
Jay has led Echo’s national brokerage operations since 2021, after joining the company in 2013; his team supports tens of thousands of carrier and shipper relationships across the U.S.

Brought to you by

Vooma — back-office automation for freight brokerages and 3PLs. Book a demo now: https://www.vooma.com/ 

Brought to you by

VOOMA — AI agents that help brokers/carriers win and move more freight. Book a demo: https://www.vooma.com/ 

What you'll learn

• Stop solving the wrong problem: Most “AI failures” are ops failures—misframed problems and incentives, not model quality.
• Zero inbound is the goal: Every inbound call is a lagging indicator that upstream work (quoting/follow-ups/coverage) slipped.
• Natural language as UI: Why chat/voice beats app labyrinths for drivers at 3 a.m.
• Orchestration > automation: Harmonize people, process, and tech so the system can triage work and scale capacity thoughtfully.
• Carrier org of the future: Cohort by strategic sourcing, advanced booking (≈48h), and coverage—and measure for carriers who want your freight, not just those who’ll take it.

Time-stamped highlights

• (00:00) Drivers don’t want a call—they want a fix: NLP and AI as “the 3 a.m. workflow.”
• (07:00) “Zero inbound” as a north star for brokers.
• (10:30) Orchestration defined: aligning process, tech, and UX.
• (14:45) Cloud-computing analogy for staffing & surge demand.
• (22:30) Pilots that flop: answering calls vs eliminating the need for calls.
• (29:45) Capacity Strategy: strategic sourcing → advanced booking → coverage.
• (36:30) “Carriers who want your freight” and how to measure fit.
• (41:45) Micro-decisions: when to post vs. invest in relationship routes.
• (43:30) Ryan’s signature: “I don’t know who needs to hear this, but…”

Links & references

• About Metafora (formerly CarrierDirect): https://metafora.net/ (transportation & logistics consulting + software)
• CarrierDirect → Metafora rebrand background: https://blog.metafora.net/rebrands-metafora-adds-industry-executive (blog + coverage)

Guest
Ryan Schreiber — Chief Growth Officer, Metafora
LinkedIn: https://www.linkedin.com/in/ryan-schreiber/

Brought to you by

VOOMA — back-office automation for freight brokerages & 3PLs (AI document handling, workflow automation). Learn more: https://www.vooma.com/

What you’ll learn

• Why averages are inflated (incumbents & core lanes) and how to price below “market” without racing to the bottom.
• Region > lane: composition scoring by market area, factoring deadhead, facility effects, and lead time.
• Cost vs. margin separation: modeling projected carrier cost at pick time, then layering margin—no black boxes.
• Automation that actually makes money: who should own it (pricing, not ops), and the cultural buy-in required.
• Speed as strategy: getting under 1s end-to-end to rank first in planners’ queues (Blue Yonder/API timeout realities).
• Participation rules: how 70–80% “respond/decide” mandates change bidding strategy—and when to opt out.
• Turning data into awards: using routing-guide gap analytics to win net-new freight.

Time-stamped highlights

• 00:01:02 — Chadd’s path from speaking at Walmart events to early enterprise 3PL customers; AVRL’s pivot to pricing.
• 00:06:09 — Elizabeth, NJ → Chicago vs. nearby Freehold: why two “identical” rates behave differently.
• 00:11:03 — How AVRL models probability of coverage by region and separates projected cost from margin.
• 00:17:06 — Who should own automated spot bidding (hint: your pricing org), and why MAPE matters.
• 00:20:00 — Market Intelligence Team: rebuilding rating engines, parallelizing data pulls, and getting sub-second.
• 00:24:45 — The real upside: 100% participation, routing-guide visibility, and data-led award wins.
• 00:29:30 — Avoiding nukes: why selective participation beats bidding “everything.”
• 00:33:55 — Benchmarks (DAT/Greenscreens): why people blame the data when they’re using it wrong.

Links & references

• AVRL homepage (company info & “18 companies per year” model). (avrl.io)
• Transport Topics on AI & optimization (AVRL’s monthly transactional volume quote). (TT News)
• Additional long-form interviews featuring Chadd & AVRL’s approach. (The Logistics of Logistics)

Guest

Chadd Olesen — CEO & Co-founder, AVRL (Austin, TX)
LinkedIn: https://www.linkedin.com/in/chadd-olesen/
Company: https://avrl.io/ (AVRL — Automation & pricing tech) (LinkedIn)

We dig into:

• Why fraud attempts spiked 27% in 2024, led by identity theft and inbox compromise 
• Highway’s new Trusted Freight Exchange (TFX)—a secure, identity-verified platform for brokers and carriers 
• Why rate confirmations in email are too risky, and the importance of real-time identity vetting 
• The tension between openness (marketplaces) and safety — how TFX leans into rules + rails over chaos 
• Culture as your firewall: why saying no and tracking overrides matter more than flashy features

Guest Bio:
Michael Caney is Chief Commercial Officer at Highway, leading efforts in identity-based verification, fraud detection, and building trust infrastructure in freight. He’s a frequent voice on freight tech, cybersecurity, and logistics strategy. See his appearances on FreightCaviar and Talking Transports. 

Why This Episode Matters:
Freight brokers and carriers often ask, “Do I really know who’s hauling my loads?” This episode arms you with facts, frameworks, and next steps to move past hope and toward certainty—before the next load vanishes.

Brought to you by:
This conversation is supported by Vooma, your AI-powered back-office automation for brokerages and 3PLs. Simplify workflows and reduce risk. Learn more at vooma.com.

What you’ll learn

• How tiny habits and “½% gains” decide championships
• Training the mind: meditation, visualization, and handling red-mist moments
• Translating driver feedback into engineering wins (and why setup can swing you 10 grid spots)
• Team culture lessons from Mercedes: incentives, information sharing, and neutralizing turf wars
• The real logistics of F1: planes, pop-up facilities, and 2,000-person teams
• Venture playbook: building access, unique value props, and backing category leaders

Guest

Nico Rosberg (2016 F1 World Champion, Founder @ Rosberg Ventures)

LinkedIn: https://www.linkedin.com/in/nicorosberg/

Sponsor

This episode is brought to you by Vooma - the AI orchestration platform that helps brokers & carriers win and move more freight. Learn more: https://www.vooma.com/

Key ideas & quotes

• “As a high-performance athlete, the half a percent makes the difference.”
• “Mostly you already know what you’re doing wrong—it’s cumulative.”
• “Embrace failure. Most failures you can bounce back from—and they’re where you learn.”
• “You can’t win alone. Information sharing beats internal rivalries—every time.”

Chapters

• Rosberg’s path: karting → Williams → Mercedes → World Title
• Performing under extreme pressure & building a mental toolkit
• Engineering collaboration and why setup beats raw pace
• Inside the F1 logistics machine
• From champion to investor: the Rosberg Ventures thesis
• Team performance frameworks founders can copy

Key Topics Discussed:

Market Analysis & Forecasting

• Why 2024 spot rate predictions missed the mark (forecast: 13-30% growth, reality: ~0%)
• The flattening of traditional freight cycles and what's driving it
• How real-time data and mini-bids are making shippers more nimble
• The shift from annual RFPs to continuous procurement strategies

Shipper Expectations & Procurement

• The growing influence of procurement teams in freight decisions
• Rising fraud concerns and carrier vetting priorities
• The balance between cost consciousness and service quality
• Why payment terms and pricing have become critical differentiators

Building High-Performing Carrier Sales Teams

• The essential traits that technology can't replace: work ethic and relationship-building
• Why AI agents won't replace human brokers for Fortune 500 accounts
• The evolving motivations of younger sales reps (hint: they're choosing time off over money)
• The importance of understanding truck drivers' experiences and challenges

Scaling a Brokerage

• Financial discipline required to scale from $50M to $1B in revenue
• The critical difference between booking loads and solving problems when things go wrong
• Buy-sell vs. cradle-to-grave models and when each makes sense
• Key metrics beyond margin: understanding cost per load in context

Industry Evolution

• Drew's hands-on approach: visiting truck stops and understanding driver life
• Why relationships and face-to-face interactions remain irreplaceable
• The role of AI and automation in streamlining operations
• Retention strategies and identifying A, B, C, and D players

Notable Quotes:

• "The rockstar is going to be the one that's able to build relationships at the end of the day. An AI agent is never going to be able to get $10 million per day out of a Fortune 500 customer."
• "Booking the load is the easiest part of our industry. The hard part is when you've got two extra pallets on the truck, or the seal's broken, or there's no appointment for four days."
• "If you're doing the easy task or looking for the easiest approach, those are things AI will replace."

Guest: Drew Herpich - LinkedIn: https://www.linkedin.com/in/andrewherpich/

Sponsor: This episode is brought to you by Vooma, the back office automation platform built for freight brokerages and 3PLs - https://www.vooma.com/

Top takeaways

• Bootstrapped & disciplined: Reinvest profits; build runway; avoid FOMO spending.
• Culture > revenue: Hire slow and for fit; “we work for our employees”; unlimited PTO.
• AI is here: Focus people on relationships & exceptions; let software handle repetitive tasks.
• Model shift: Hybrid cradle-to-grave + split supports higher volume/enterprise.
• Scaling math: Targeting 40–50 loads per ops rep/day with today’s tools.
• Counter-cyclical: Be ready to hire into down markets; measure ROI on a 12-month horizon.

Guest & company links

• Ali Shafi (LinkedIn): https://www.linkedin.com/in/shafiali/
• SIO Logistics (Website): https://sionow.com/

Tools mentioned

• Vooma (AI for brokers): https://www.vooma.com/

Chapter Markers (mm:ss – topic)

• 00:00 – Intro & Ali’s origin story
• 01:00 – From big-box brokerage to founder
• 03:30 – Bootstrapping realities: cash flow, prepaying carriers, factoring credibility
• 06:30 – Partnering with Cody Brown: trust & complementary lanes
• 09:30 – First hires, first office, first $1M in sales
• 12:00 – Culture over short-term revenue; unlimited PTO
• 15:00 – Why no outside capital (freedom & discipline)
• 18:00 – AI to erase “let me check” work; instant status & notifications
• 21:00 – Hybrid cradle-to-grave + split model for enterprise volume
• 24:00 – Load-to-rep targets (path to 40–50/day)
• 27:00 – Greedy when others are fearful: scaling in a down market
• 30:00 – Tech ROI over 12 months; change management that sticks
• 33:00 – Market cycles, mental game, and thick skin
• 36:00 – Biggest surprises & advice to new brokers

Notable Quotes (optional pull-quotes)

• “If you’re saying AI is coming, you’re already behind.”
• “We’ll choose culture over money—every time.”
• “Today is the worst AI will ever be.”

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This episode is brought to you by Vooma - https://www.vooma.com/.
Level up your brokerage ops with automated quoting, instant status updates, and AI-assisted workflows. 

From early experiments—including wild ideas like training crows for last-mile delivery—to killing the wrong projects and zeroing in on freight’s biggest bottleneck, unstructured data, this conversation highlights the relentless problem-solving and intellectual honesty behind Vooma’s rise.

We cover:

• The origin story of Vooma, including how a South African slang word became the company name
• Early pivots, experiments, and lessons from projects that didn’t make it
• Why solving unstructured data entry unlocked massive opportunities for brokers and 3PLs
• The founders’ decision to build an in-person company in San Francisco and the trade-offs involved
• Vooma’s core values: hands-on execution, long-term games with long-term people, intellectual honesty, and “run with the ball” ownership
• How AI co-workers will reshape the freight broker role—removing repetitive tasks so humans can focus on strategy, growth, and customer relationships
• Why building culture, humor, and resilience matters as much as the tech itself

Mike and Jesse also share the books that shaped their thinking—from The Mom Test to Thinking, Fast and Slow—and even tackle the ultimate startup question: Would you rather fight one horse-sized duck, or a hundred duck-sized horses?

Chapters

• 00:00 – Welcome & Introduction
  Setting the stage for how AI and automation are reshaping freight.
• 00:34 – Meet Mike & Jesse
  The chance introduction that led to founding Vooma.
• 02:00 – Early Impressions & Complementary Skills
  Why their different strengths made them better together.
• 04:30 – Crazy Early Experiments
  From training crows to robotic last-mile delivery—what worked, what didn’t.
• 07:00 – Killing the Wrong Projects
  Lessons from pivots and finding the right entry point.
• 08:00 – The Origin of “Vooma”
  How a South African slang word shaped the brand.
• 09:00 – Discovering the Real Bottleneck
  Why unstructured data entry was freight’s hidden pain point.
• 13:00 – The Future of Freight Brokers
  AI co-workers, strategy over grunt work, and what brokerages look like in 5 years.
• 17:00 – Scaling With AI Agents
  Optimizing workflows, market visibility, and clearing inefficiencies.
• 18:30 – Why Build In-Person in San Francisco
  Trade-offs of geography, networks, and startup speed.
• 20:00 – Vooma’s Core Values
  Hands-on execution, long-term games, intellectual honesty, and “run with the ball.”
• 24:50 – Culture & Humor in the Trenches
  Why resilience and laughter matter in startups.
• 25:30 – Deep Dive Interviews
  How Vooma’s unique hiring process uncovers true values and fit.
• 27:30 – Books That Shaped the Founders
  From The Mom Test to Atlas Shrugged to Thinking, Fast and Slow.
• 30:00 – The Final Question
  One horse-sized duck vs. a hundred duck-sized horses—co-founder answers revealed.

Chapters:
00:00 — The hard lessons of first-time leadership
03:30 — Axle’s trajectory: from ~$17M to $1B+
07:30 — Culture as strategy: “Build your empire” and loud sales floors
12:00 — Avoiding micro-cultures when scaling offices
16:30 — Hiring at pace: signals that actually matter
22:00 — Training at scale: LaunchPad’s six-week ramp
27:30 — Retention: base vs. commission, fairness, and grind
34:00 — Where to automate first (repeat touches, doc QA, quoting)
41:30 — Keeping the human: when relationships beat automation
47:00 — Surviving soft markets: travel > excuses
52:30 — Leadership evolution and feedback loops

Key Takeaways:

• Culture is Axle’s #1 growth strategy — lose that, and you lose everything.
• LaunchPad’s six-week program speeds ramp time and improves throughput.
• Automate repetitive touches (document checks, quoting) but never the relationship.
• In down markets, Axle increases customer travel rather than cutting it.
• Hiring focuses on energy, work history, and coachability — not just interview polish.

Memorable Quotes:

• “Culture is number one in the strategy for growth.”
• “Automate the repetitive; never automate the relationship.”
• “Travel is the last thing you cut in a soft market.”

Links & Resources:

• Shawn McLeod — LinkedIn
• Axle Logistics — Website

Sponsor:
This episode is brought to you by Vooma — AI that unlocks revenue in your team’s inbox with automated quoting, order entry, tracking, and more. Learn more at Vooma.com.

What We Cover

• Career arc: Management trainee → dispatch → brokerage launch → ARL presidency
• Hybrid operating model: Staffing-assisted cradle-to-grave (Colombia ops + US client touch)
• Train-the-trainer: “Four super users” to eliminate perpetual entry-level retraining
• Sales structure 2.0: Splitting hunters (sales) and BDR/CS to speed response & enforce SLAs
• People vs process: EOS/Traction, shadow-work, and deleting steps before automating
• Tech partnerships: Why ARL co-builds with vendors and aims for 80/20, not edge cases
• Automation lens: Start with mundane, API/RPA bridges, humans as exception managers
• Data reality: TM3→TM4 migration, standardizing inputs, and the prize of drayage pricing data
• Risk & resilience: Receivables caution, tariffs, and modal shifts (intermodal ↔ OTR)
• Culture: Small wins daily, continuous training, and giving offshore teams a real voice

Playbook & Tactics

• Sit tech next to the business. Proximity shrinks build cycles and bakes in reality.
• Free reps to sell. Move load-building, T&T, and intake to an ops pod first—then automate.
• Design for exceptions. Automate 6–7 steps in a 10-step flow; humans handle the rest.
• Standardize input fields. Clean data starts at the source; train against exceptions.
• Measure the ROI. Track time saved, licenses retired, and throughput per seat.
• Organize for strengths. Separate “people-first closers” from “process-first executors.”

Notable Quotes

• “If the tech people would just sit next to the business people, you build product fast.”
• “Train four super users and you never have to train entry-level again.”
• “Those are two different roles—very few are great at both.”
• “Our motto is small wins every day.”

Resources Mentioned

• ARL Logistics (brokerage & agent network)
• US1 Industries (parent; proprietary TMS)
• Lean Solutions Group (nearshore ops)
• EOS / Traction (operating system)
• The Revenue Engine by Kara Brown (sales/marketing alignment)

Sponsor

Vooma — Back-office automation for freight brokerages. From AI document handling to ops streamlining, scale without the growing pains.