FreightMath Alliance

Fall 2026 Meeting

Two Days of FreightMath

Oct 6–7, 2026Indianapolis

KSM Headquarters · 600 East 96th St., Indianapolis, IN

Monday, October 5 · Arrival & Welcome
6:00 p.m.
Informal Arrival & Welcome Dinner · Firebirds

Casual dinner and mingling as people arrive. Firebirds is a short walk away, and dinner is on us. Drop in any time from 6:00 p.m. onward.

Tuesday, October 6
7:00 AMBreakfast & Networking · 3rd Floor
8:00 AM
Welcome
Chris Henry, FreightMath
  • State of the Alliance: where things stand since Spring, membership and engagement, and what has shipped.
  • FreightMath Roadmap Preview: a fast first look at what is new across the platform and what is on the roadmap, setting up the sessions that follow.
  • The two days ahead: what to expect.
8:30 AM
MapLedger: Current State & Benchmarking
Pete Richards, with Chris Henry
  • FreightMath Adjusted Revenue: how we scale costs so the FreightMath OR aligns with the OR from your GL.
  • Benchmarking: the standardized chart of accounts is what makes apples-to-apples benchmarking possible across the Alliance.
  • Best practices & use cases (discussion): how members are using MapLedger today and tackling common problems.
9:30 AM
Segment-Level Costing
Dave Dunst, FreightMath
  • How it works, end to end: a full walk-back now that SLC is live and members have seen the results.
  • Driver pay: how compensation is distributed down to the individual segment.
  • Allocation of Cost Buckets: how each bucket is allocated to segments.
  • Deadhead Models: choosing a deadhead model (pre, split, post).
  • Forecasting: how segments are costed before the GL month closes.
10:30 AMBreak
10:45 AM
FreightMath Platform Improvements: Dashboard & Spot Check / Trip Check
Adam Smith & Jordan Nelson, FreightMath
  • Dashboards: the current state of the FreightMath dashboard, including the new features and pages added since Spring.
  • Spot Check & Trip Check: the apps that put load- and trip-level OR in front of the pricing and dispatch decision, worked hands-on in the FreightMath app at app.freightmath.com. Bring your login.
12:00 PMLunch
1:00 PM
The 5 Strategic Mistakes That Sink Change in Trucking (and How to Avoid Them)
Jim Stockeland, Fractional COO, Your C-Suite, with Abby Ryan, President, Crawford Trucking, and Max Herbst, Vice President of Finance, Leonard's Express
  • Pitfall 1: Starting with the tool instead of the target.
  • Pitfall 2: Nobody owns it (role confusion).
  • Pitfall 3: Mistaking go-live for the finish line.
  • Pitfall 4: Keeping the old way running “just to be safe.”
  • Pitfall 5: Asking a maxed-out team to run the business and lead the change.
1:45 PM
Beyond AI Fatigue: Why Trusted Data Comes First
Moderated by Eric Jacobson, CEO, Tivitri, with Adam Blanchard, Double Diamond, and David Knight, Data Engineer, Tivitri

Every fleet is being pitched AI, and most are tired of hearing about it. The operators getting real results have learned that nearly every significant operational problem eventually becomes a data project. This panel shares a real-world look at how unifying operational data (telematics, TMS, and back-office systems) into a trusted master data set makes AI practical, reliable, and worth the investment.

  • AI fatigue: why so many AI initiatives stall in fleet operations.
  • Operational problems become data problems: why the work routes back to data.
  • Clean, connected data: building trustworthy telematics and operational data.
  • Master data and AI: applying AI in ways leaders can trust.
2:45 PMBreak
3:00 PM
How Carriers & FreightMath Are Using AI, Part 1
Facilitated by Chris Henry
  • Agent Challenge report-back: members show the agents they built since Spring and what they saved.
  • Live use cases: spot-pricing bots, daily fuel-optimization maps, driver-risk monitoring, back-office and agentic workflows, and institutional memory via Claude Projects.
  • What is working: vendor AI versus internal build.
4:00 PM
BidRight
Austin Knobloch, Director of Product Development, Nussbaum Technology
  • Where BidRight is Today: Bid import to commitments, FreightMath built in.
  • Use of AI: Auto Rate with Reasoning, Contract Ingestion, Bid Insights.
  • Where BidRight is Going: Selections from our roadmap.
5:00 PM
Closing and Adjourn
Chris Henry

6:00–8:00 PM
Networking Event

Dinner and Relationship Building at Culinary Dropout

1320 E 86th St, Indianapolis, IN 46240

Sponsored by Tivitri

Wednesday, October 7
7:00 AMBreakfast & Networking · 3rd Floor
8:00 AM
Securing Profitable Dedicated Freight
Brad Heisterkamp, FreightMath
  • Advanced dedicated pricing techniques: pricing the fleet, the driver, and the schedule instead of the lane, so the rate covers what dedicated actually costs to run.
  • Marketing to dedicated opportunities: finding and positioning for the shippers whose freight fits a dedicated model, and making the case with FreightMath data.
  • Contractual guardrails: the terms that protect the business once the freight is won — volume commitments, rate adjusters, and exit provisions.
8:45 AM
How Carriers & FreightMath Are Using AI, Part 2
Facilitated by Chris Henry, FreightMath
  • Where AI is moving OR: and a working framework to quantify the return.
  • Governance & data handling: keeping driver, customer, and employee data out of un-consented models.
  • Your next step: one automation to put in place before Spring 2027, plus resources like Anthropic Academy.
10:15 AMBreak
10:45 AM
Future of FreightMath
The FreightMath Team
  • Telematics: integrating telematics to replace inferred miles with actual miles, targeted for next year, for more precise hours and cost.
  • Machine learning: the normalization and prediction layer, including hours-of-service normalization that estimates reload potential beyond what the raw data shows.
  • Insights: a triage-style start page that surfaces prioritized action items on login, dismissible and logged, so the platform tells you what to act on.
  • Fuel cost: lane- and segment-level fuel costing with a per-segment fuel index for far more geographically accurate cost.
  • Dedicated pricing: the advanced dedicated pricing wizard and cafeteria-style contract generator, taking a carrier from pricing model to a customer-ready contract.
  • Freight vs. ops: separating pricing quality from operational execution, so a lane reads as what actually happened against what could have happened under standard operations.
  • Control Room App: Broker/Shipper, new area control, trailer pools, strategic footprint, custom network logic, charges and more.
12:00 PMLunch
1:00 PM
MileMaker: The Latest in Mileage & Routing
Peter Espinosa, CEO, MileMaker
  • Where the miles do differ, it is real: MileMaker updates its maps four times a year, so a changed weight restriction or road closure shows up as a genuine, defensible difference.
  • Why it matters: miles and time are the denominators in nearly every transportation metric, and routing you can count on is what keeps those numbers accurate.
1:30 PM
How Carriers & FreightMath Are Using AI, Part 3
Facilitated by Chris Henry, FreightMath
2:30 PM
Closing Remarks, Key Takeaways & Save the Date
Chris Henry

3:00 PM · Adjourn · Safe travels home