About the role
Senior Director of Marketing — Agent-Led
Portpro is hiring a Sr. Director of Marketing to build and run an agent-led marketing org. This is not a traditional marketing leader role. You'll architect the systems, agents, and workflows that make marketing operate at machine speed — and you'll lead through them.
What you'll own:
- Design and ship the agent stack that powers content, demand gen, lifecycle, and ops
- Operate as a builder-leader: prototype agents yourself, then scale what works
- Use the leverage to move faster than a traditional team 5x your size
- Set strategy and brand for Portpro across the drayage / logistics SaaS market
- Hire selectively — small team of operators, heavy on tooling
What we're looking for:
- You've built and deployed agents in production (marketing or adjacent)
- Strong marketing leadership track record — demand gen, content, or growth at a B2B SaaS
- Hands-on with modern agent frameworks and LLM tooling
- Bias toward shipping over planning
About PortPro
PortPro is a privately-held SaaS company founded in 2019 that provides drayage-specific transportation management software under the brand 'drayOS.' The platform serves drayage carriers, freight brokerages, and owner-operators at major U.S. ports and rail yards, covering order entry, dispatch, container tracking, invoicing, and AI-powered automation. The company raised a $12M Series A in January 2023, has grown 1,600% between 2020 and 2023, and ranked 84th on Deloitte's Technology Fast 500 in 2024.
Job details
Salary
$175,000 - $300,000
Equity
Up to 0.5%
Location
Remote
Funding
Total raised
$12M
Last stage
Series A
Investors
Founders
Toni Ann Careccio
Co-Founder & Chief Customer Officer
What happens next.
No applications, no recruiter spam. Just the intro.
Confirm the fit
A few questions to make sure this role is the right shape for you. Two minutes.
I pitch you to the company
I write the intro, send it to the founder, and handle the back-and-forth.
A meeting lands on your calendar
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.