GTM Engineer / AI Ops Manager

Reports to: Senior Director, Marketing

Location: Remote

Type: Full-time

About Our Client

Our client is an AI-led operating system for the drayage industry. They power trucking companies that move containers in and out of the ports, a mission-critical often overlooked corner of the supply chain.

Drayage is a fragmented, relationship-heavy market with over 80% of carriers running fewer than 20 trucks, and they don't respond to mass-blast outbound. Winning here requires a GTM motion that's smarter, more researched, and more personalized than the rest of freight tech. That's where this role comes in.

The Role

We're hiring our first dedicated GTM Engineer to sit at the intersection of sales, marketing, and product. You'll build the systems, workflows, and AI-powered tooling that let a focused revenue team generate an enterprise-grade pipeline without enterprise-grade headcount.

If you've ever looked at a sales motion and thought "this could be 10x more efficient with the right stack, the right data, and a few well-placed LLM calls" this is the role for you. You'll have the rare combination of a real ICP (drayage carriers and brokers), a rich domain (FMCSA data, port operations, chassis pools, intermodal flows), and autonomy to build.

What You'll Own

Outbound & Account Intelligence

• Build and maintain enrichment pipelines that combine FMCSA SAFER data, port activity signals, fleet composition, chassis ownership, terminal proximity, and TMS incumbency to score and prioritize drayage carriers and brokers

• Develop LLM-powered personalization workflows in Clay, Apollo, or similar so every outbound touch references the prospect's actual operating reality, not a generic "growing your trucking business" pitch

• Stand up intent-data and remarketing reconciliation flows across our tech stack
  

Sales Enablement & Pre-Call Intelligence

• Productize pre-call intel briefs into automated, repeatable artifacts AEs can pull on demand

• Build and maintain competitive battlecards and displacement playbooks for our most common takeouts (CompCare/Compcare, Profit Tools, Trinium, McLeod, Tailwind, in-house systems)

Call Intelligence & Revenue Analytics

• Build pipelines from Gong (or successor) into LLM workflows that produce daily/weekly sales reports, surface objection patterns, flag at-risk deals, and feed competitive intel back to product and marketing

• Partner with RevOps to build attribution, conversion, and velocity dashboards that actually inform decisions not just decorate Monday meetings
  

Field & Event Activation

• Build the systems behind PortFest, Drive, TPM and regional drayage association events: pre-event prospect lists, post-event nurture flows, on-site demo capture, attribution back to pipeline

• Help marketing run experiments on messaging, positioning, and channel mix and instrument them properly so we learn from what works
  

Internal AI Tooling

• Stand up and govern internal AI workflows the GTM team uses daily: prompt libraries, custom Claude/GPT projects, RAG over our content library, MCP integrations with our CRM and call platforms

• Be the person who decides when a workflow should be a Clay table vs. a Python script vs. a real product request to engineering
  

What We're Looking For

Required

• 3+ years in a GTM Engineering, RevOps, Sales Engineering, or Growth Engineering role and a bonus if any of that was at a vertical B2B SaaS company

• Working proficiency in Python and SQL; comfortable in JavaScript when needed

• Deep, opinionated fluency with the modern GTM stack: Clay, Apollo (or similar), Gong, Salesforce, HubSpot, LinkedIn

• Hands-on experience building with LLM APIs (Anthropic, OpenAI) prompt design, tool use, evals, cost management

• A track record of shipping systems that demonstrably moved a revenue metric: pipeline created, meetings booked, win rate, cycle time
  

Strongly Preferred

• Domain knowledge in freight, logistics, supply chain, or trucking or proven ability to ramp on a complex vertical fast

• Familiarity with FMCSA data sources (SAFER, L&I, MCS-150), or analogous public/regulatory datasets in another vertical

• Experience with MCP, agent frameworks (LangGraph, CrewAI, etc.), or production AI Orchestration
  

You'll thrive here if you

• Get genuinely curious about the operational details of how a drayage carrier makes money: chassis splits, per diem, demurrage, accessorials, the difference between asset-based and brokerage authority

• Default to building rather than briefing; You'd rather ship a v1 in a week than write a 20-page requirements doc

• Treat AEs and CSMs as your customers; their adoption of what you build is the measure of whether it worked-

• Are comfortable being the only person in the room who knows how a particular system actually works, and write things down so that changes
  

What Success Looks Like

• By 90 days: Pre-call intel briefs and account enrichment are running on automation for the AE team; outbound personalization quality is measurably higher

• By 6 months: Pipeline created per SDR/AE has meaningfully increased through better targeting and tooling

• By 12 months: PortPro's GTM stack is a competitive advantage and visiting peers from other freight tech companies leave wanting what we have