Director of Transportation Safety, Risk & Outcomes

Help Build What Comes Next in HOS & Transportation Safety

You’ve spent years working with drivers, fleets, safety programs, compliance, claims or transportation risk.

You’ve seen drivers complete training and still struggle to apply it. You’ve seen violations that another course alone wouldn’t solve. You may have also seen experienced drivers make sound decisions under difficult operating conditions that a simple report never captures.

What if your experience could help build a system that makes those distinctions visible?

HOSoptima is looking for an experienced transportation professional to help build our HOS Risk & Outcomes Intelligence function.

We want someone who can connect practical industry experience with evidence, measurement and sound judgment.

Someone who asks better questions, challenges easy explanations and helps turn years of knowledge into a system the company and its customers can repeatedly use.

REQUIRED: COMMERCIAL TRANSPORTATION BACKGROUND

This role requires substantial professional experience in commercial transportation safety, fleet operations, motor carrier compliance, transportation risk, or commercial vehicle insurance and claims.

You should have worked directly with commercial drivers, trucking fleets, motor carriers or organizations that serve them. You must be able to explain how driver operations, Hours of Service, safety records and business pressures can affect fleet outcomes.

Your experience may come from roles such as a fleet safety director, motor carrier compliance leader, transportation risk or loss-control professional, commercial trucking insurance or claims professional, telematics specialist, or transportation researcher.

We also need more than experience reviewing compliance records. Tell us what you have personally investigated, measured, built or improved, how you evaluated the result, and what the evidence did—and did not—support.

General workplace safety, warehouse safety or sales experience alone does not meet the transportation-background requirement. Experience in those areas can add value when combined with substantial commercial transportation experience.

IMPORTANT — FOUNDING STAGE COMPENSATION

HOSoptima is bootstrapped. This opportunity does not currently include a conventional cash salary.

The selected operator may have the opportunity to earn meaningful ownership through defined deliverables, milestones, continued contribution and durable enterprise value.

Responsibilities, economics, authority and other engagement terms would be agreed and formally documented before substantive work begins. Ownership and future cash compensation are not guaranteed.

If you need immediate salaried employment, this opportunity won’t meet that need today.

If you’re interested in helping build a transportation technology company around problems you understand firsthand, keep reading.

ABOUT HOSOPTIMA

HOSoptima is a transportation technology and education company initially focused on Hours of Service understanding and application.

Our MVP is built. We’re in QA and commercialization.

Our product foundation includes HOS assessments, scenario based learning, module quizzes, remediation, final assessments, private certification, credential verification, fleet administration and reporting.

Our larger direction connects demonstrated understanding, interventions and, eventually, authorized operational evidence.

The questions behind the company are straightforward

Does the driver understand how to apply HOS?

What support is needed?

Did the intervention help?

What happened afterward?

What can the fleet reasonably conclude from the evidence?

ELDs, training systems and safety departments already perform important work. We’re building a complementary layer that helps connect information those systems don’t necessarily explain on their own.

Future ELD integrations and advanced operational intelligence are part of our direction. They should not be assumed to be live today.

THE OPPORTUNITY YOU WOULD OWN

Your mission would be to help HOSoptima determine whether its work is producing meaningful results—and build the methods and processes needed to evaluate those results responsibly.

Consider two drivers with similar recorded HOS issues.

One may demonstrate a gap in understanding. Another may understand the rule but face an operational problem that requires a different response.

Or consider two drivers with no recorded violations.

One may have demonstrated strong understanding through demanding situations. We may have very little evidence about the other.

The record matters. Understanding what it does and doesn’t establish matters just as much.

We want someone who can help fleets examine those differences without jumping to conclusions.

WHAT YOU WOULD HELP BUILD

Working directly with the Founder & CEO and the other operating functions, you would help establish:

• Practical measures of demonstrated HOS understanding.
• Pilot plans that define what we’re testing and what success would mean.
• Methods for evaluating training and other interventions.
• Clear definitions for the information we collect.
• Processes for reviewing missing, conflicting or unreliable records.
• Ways to examine repeated issues and relevant operating circumstances.
• Reporting that distinguishes observations from explanations.
• Requirements that help Engineering capture the right information.
• Evidence standards for customer reports and commercial claims.
• A growing foundation for future fleet, research and insurance relationships.

You wouldn’t need to arrive with every answer.

You would need to recognize weak assumptions, identify what’s missing and help build a defensible approach.

YOUR TRANSPORTATION BACKGROUND MAY TAKE DIFFERENT FORMS

You may currently be a

• Safety Director or transportation safety executive.
• Fleet compliance or operations leader.
• Transportation risk or loss control professional.
• Insurance or claims professional with substantial fleet experience.
• Telematics or driver performance specialist.
• Transportation researcher or applied analyst.
• Driver development or training evaluation leader.
• Consultant who has built meaningful safety and performance programs.

Substantial commercial transportation and HOS understanding are required. You must also be able to work with evidence, identify missing information and explain what the available data can—and cannot—support.

You don’t need to have held a position called “Risk & Outcomes Intelligence.”

We’re interested in what you’ve personally built, measured, investigated and improved.

Substantial HOS and commercial transportation understanding matters. So does the ability to work with data and explain what it supports.

Advanced education, publications and technical skills can strengthen your background. They don’t replace demonstrated judgment.

THE EXPERIENCE WE WANT TO HEAR ABOUT

Perhaps you’ve:

• Built a safety program and evaluated whether it worked.
• Investigated recurring problems and found that the initial explanation was incomplete.
• Connected driver behavior, operational circumstances and safety records.
• Used telematics or inspection information to guide interventions.
• Evaluated claims or losses without assuming the first apparent cause was the correct one.
• Developed reporting that changed how executives made decisions.
• Designed research or evaluation methods others continued using.
• Challenged a reassuring metric because it didn’t measure what people thought it measured.

Tell us what you personally did.

What information did you use? What changed? What remained uncertain? What continued working after your involvement?

THE KIND OF LEADER WE WANT

We want someone who takes ownership.

You should be willing to challenge the founder, work directly with the team and help improve what already exists.

Early work will be hands on. It may involve reviewing assessment records, defining a pilot measure, questioning a dashboard or explaining why a proposed claim goes beyond the available evidence.

Public speaking and industry relationships are useful. The central responsibility is building the function.

Your knowledge should become methods, requirements and processes that others can reliably use.

That’s how individual expertise becomes durable company value.

BUILD SOMETHING VALUABLE. HAVE THE OPPORTUNITY TO OWN PART OF IT.

You’ve spent years developing knowledge that organizations depend on.

At HOSoptima, you could help turn that experience into something that continues creating value: a measurement system, an evidence methodology and an intelligence function that customers rely on.

That contribution could become an important part of what makes this company valuable.

We want the person who helps build that capability to have an opportunity to earn meaningful ownership in the company.

Ownership would be tied to agreed milestones, continued contribution and durable enterprise value created. The specific opportunity would be negotiated and documented before work begins, subject to required approvals.

Our ambition is to build a high growth transportation technology company with national relevance and the potential for a significant future acquisition or other liquidity event.

We can’t promise that outcome or what any ownership would ultimately be worth.

But we can be clear about our intent

If you help build a durable part of HOSoptima, we want your opportunity to reflect the significance of what you create.

Three years from now, the question won’t simply be how many meetings you attended or reports you reviewed.

It will be

What exists because you built it—and how much stronger is the company because it does?

TO APPLY

Please submit your resume or CV and briefly answer

1. What part of your experience best prepares you to connect HOS, driver understanding, operational circumstances and fleet outcomes?

2. Describe a safety program, intervention, investigation or analytical process you personally built or improved. How did you determine whether it worked?

3. Tell us about a time the available data didn’t support the explanation others wanted to accept. What did you do?

4. Are you comfortable exploring the founding stage compensation structure described above, and what availability could you realistically commit?

HOSoptima, Inc.

Help turn transportation experience into intelligence the industry can use.

Pay: $80,900.00 - $197,500.00 per year

Work Location: Remote