From Playbook to Proof: What TMSA Leaders Took Home from the 2025 Executive Summit

Two days in Chicago (Oct. 22–23) gave sales and marketing leaders in transportation and logistics a clear mandate: combine people-first leadership with sharper commercial systems - and get practical about AI, risk and relationships.

In a market where capacity swings fast and tech buzz is louder than ever, the 2025 TMSA Executive Summit crystallized three truths:

1. Buyers aren't purchasing lanes - they're buying confidence.
2. Growth comes from disciplined systems and skilled people.
3. AI will reshape roles, but leaders who train and govern it well will create the advantage.

This Summit recap aims to provide you with an executive-ready field guide you can act on today.

The context: volatility favors the prepared

Louis Pasteur said it first: Chance favors a prepared mind.

But it takes more than luck to survive in today's dynamic trade environment. Traditional tactics aren't enough. Global sourcing has shifted, seasonality is unreliable and risk surfaces in new places, from cyber threats to geopolitical shocks.

Leaders need resilient commercial engines: buyer rapport, cross-functional coordination, credible advisors at the table and a clear ruleset for responsible AI.

Summit highlights that moved the needle

AI: Govern it, guardrail it and make it earn its keep

The signal: Teams are using AI daily, but maturity is rare - and fear persists when training is absent.

What mattered: A practical framework by Chris Peer from SyncShow emphasized four pillars - Strategy, People, Systems and Software. Tie AI to SMART outcomes (e.g., “cut content cycle time 30%”), assign role-level objective-key results and run 90-day sprints to document prompts, integrate SOPs and measure ROI.

On prompts, Peer's C.R.I.T. framework (Context, Role, Interview, Task) raises quality; custom assistants grounded in your brand assets improve consistency.

Guardrails: Without federal omnibus rules yet, your existing obligations still apply, said Attorney Kristopher Chandler of Benesch Law. Build policy around privacy, bias testing, security and human oversight; scrutinize vendor contracts for data rights, model changes and termination paths.

When developing your team's AI training, Peer cited author Geoff Woods: "Your competitive advantage is not knowing everything about AI; it's about asking the right questions and being curious."

Strategic sales leadership: systems beat heroics

The signal: Control the controllables - plan, culture and behaviors.

What mattered: Design a high performance team (slow to hire, quick to course-correct), onboard deliberately, coach weekly and connect pay to clearly defined KPIs.

Mike Riccio and Drew Cherba of More Than Miles Consulting emphasized that accountability is specific and rhythmic: set numbers, track them, review them, reward them.

Three growth levers:

• Retention: Calendar the relationship. Know strategic goals, non-price drivers and renewal risks.
• Expansion: Aim higher and wider in each account; diversify contacts and channels.
• Acquisition: Balance patience with persistence; choose a team model (pod/split/hybrid) and assign roles across hunting, account management and ops.

People-first leadership is the multiplier

The signal: Trust-rich cultures outperform.

What mattered: Put employees first: transparent financials, frequent feedback and clear career paths. Nicole Glenn, Founder of the Candor Companies, revealed that recognition tied to values beats novelty perks. When leaders model vulnerability, the result is faster learning and better retention.

AI angle: Reduce fear with training and communication. AI automates routine; humans double down on relationships, strategy, empathy and creative problem solving.

Mantra: “Test, Talk, Tweak, Thrive.”

Resilience as a commercial advantage

The signal: Sourcing footprints are moving; uncertainty is the norm.

What mattered: Shippers buy freight - but they want confidence, Mohawk Global's Anthony Pagnotto said. Winning partners bring options across modes, explain trade-offs clearly and operate with psychological safety so teams can make high-speed decisions without fear.

Freight fraud is a $35B drain, and much of the room had seen it this year. ITS Logistics’ multilayer playbook shrank its carrier base while growing volume 20% YoY, and drove incidents to 0.004% by pairing rigorous SOPs with physical verification and GenLogs’ ground-truth data.

A surprise edge: Deep expertise sells. A former compliance leader outperformed traditional sellers by educating customers and coaching decisions with clarity, not just quotes.

What shippers actually want (and notice)

A powerhouse panel of shipping execs from Google, KeHE Distributors and Mitsubishi Power Americas, moderated by logistics entrepreneur Andrew Silver of The Freight Pod, spoke candidly about the pitches they've received and what resonates with them.

The signal: Specificity beats swagger.

What mattered: Do your homework. Speak the customer's business, not generic outreach. Bring evidence (e.g., multi-year data that surfaces hidden inefficiencies). Follow up with respectful persistence, not spray-and-pray. Start with one real problem - solve it thoroughly - then scale.

Character test: During disruption, a vendor honored below-market rates and later, the shipper (!) fought to keep fair terms when the market flipped. That integrity - representing a true partnership - unlocked loyalty beyond an RFP cycle.

The lesson for sales and marketing professionals is profound: integrity in adversity creates loyalty that transcends any RFP cycle.

Mountain Movers: two playbooks for modern marketing and sales

The signal: Different paths, same fundamentals.

What mattered:

• Revenova Marketing Manager Mike Marut: A data-first, one-person marketing engine matured into a team by proving ROI - tracking the funnel, tying events to opportunity creation and iterating in real time with the news cycle.
• Matson Logistics Director of Strategic Accounts and Government Services John Lemieux: Legacy + innovation = advantage. Leaders teach the “why” behind cost and rate structures, and mentor across functions because, "We're nothing without our teams."

Scaling commercial operations: clarity is kind

The signal: Complexity (EV shifts, multimodal growth, security risks) demands cleaner systems.

What mattered:

• Forecasting & focus: Prioritize core customers; if it's not in the CRM, it didn't happen, said Trip Wiygul of Total Transportation of Mississippi.
• Integrated data: Lori Kincannon of McKinney Trailers discussed how their business stitches CRM, billing, fleet and service data for a 360° view, so the front line can act quickly.
• Playbooks: Codify top/mid/bottom-funnel actions so teams are self-sufficient. As a leader, the goal isn't to be the superhero - it's to build a team of superheroes, said Matt Wagner of Jarrett.
• Leadership cadence: Executive sponsors join key account reviews; the whole company owns relationships, not just sales.

Holly LaBoda from Luminaries Consulting summed it up: Leaders must "look up and out" to maintain clarity, alignment, resilience, and agility - but none of it matters without growing your people to keep pace with the business.

Implications for transportation & logistics leaders

For revenue leaders (CROs/CSOs):

• Replace activity vanity with results clarity. Instrument retention and expansion with distinct KPIs and cadences.
• Recruit for learning velocity and business acumen - not just rolodex size. Consider specialists (compliance, trade, engineering) in consultative sales roles.

For marketing leaders (CMOs/VPs):

• Make AI operational: define role-level targets, standardize prompts and measure cycle-time, asset reuse and lead-to-op metrics.
• Treat content like a newsroom: tie messaging to live events (disruptions, regulatory moves) and package fast, with proof.

For CEOs/Founders/Owners:

• Invest in manager quality. Coaching muscles are the constraint on scale.
• Update governance: AI policy, data contracts and incident playbooks need owners and reviews.
• Model transparency - financial and strategic - to earn discretionary effort in the hard quarters.

Proof that helps you persuade internally

• People-first pays: High-trust cultures correlate with outsized performance; teams reported engagement lifts after leadership shared numbers, admitted misses and used EOS-style cadence.
• Expertise closes: Educator-sellers - those able to map options and risk - won complex deals even against lower rates.
• Systems reduce heroics: Teams integrating CRM + ops data shortened decision cycles and contained margin pressure by shifting capacity or productized services (e.g., storage).

What to do next (90 days, pick a track)

Now (Weeks 1–3):

1. Name one buyer problem you'll own this quarter; gather 3–5 customers for discovery.
2. Stand up an AI sprint: pick one repetitive workflow (e.g., call notes → brief → email) and baseline cycle time; implement CRIT prompts and a light governance checklist.
3. Clarify KPIs: define separate scorecards for retention, expansion and acquisition; align comp and inspection rhythm.

Next (Weeks 4–8):
4) Instrument your CRM: required fields, stage exit criteria and executive-sponsor flags for top accounts.
5) Package a “confidence kit” for shippers: three routing options with trade-offs, risk notes and trigger points for switching.
6) Publish two “newsroom” pieces tied to current disruptions or regulatory changes; measure assisted pipeline.

Later (Weeks 9–12):
7) Integrate data sources (CRM, billing, ops) for a 360° view and dashboard the top five decisions sellers make weekly.
8) Run an integrity audit on contracts and comms: where would you hold firm in a crunch? Codify the expectation.
9) Coach the coaches: launch a weekly manager huddle to review deals, pipeline hygiene and skills.

TMSA Members: Dive deeper with the resources in the TMSA portal, then pick one 90-day play to pilot with your team.

Not yet a member? Join TMSA to access frameworks, peers and practical tools you can apply on Monday.

This content was sponsored by the Jacksonville Port Authority (JAXPORT), your global gateway to Florida, the nation’s third-largest state. Dozens of ocean carriers call at JAXPORT, offering you competitive transit times to 140 ports in more than 70 countries. JAXPORT offers shippers seamless transportation via 150+ trucking firms and 40 daily trains via Class I railroads CSX and NS and regional rail line FEC.