P

PortPro

SaaS TMS for drayage container shipments

Director of DevOps

Full-Time
No salary listed
Expert
Los Angeles, CA, USA
Remote
DevOps & InfrastructureCloud Engineering, DevOps Engineering

About the job

Requirements
  • 10+ years of experience in DevOps, SRE, or Cloud Engineering, with at least 3+ years in a leadership role
  • Proven experience with cloud platforms (AWS, GCP, Azure) and Kubernetes
  • Expertise in CI/CD pipelines, infrastructure-as-code (Terraform, CloudFormation), and automation
  • Strong knowledge of networking, security, and monitoring tools
  • Experience with microservices, containers, and distributed systems
  • Hands-on experience with GitOps, DevSecOps, and SRE principles
  • Strong leadership, communication, and cross-functional collaboration skills
Responsibilities
  • Define and execute the company's DevOps roadmap. Lead and mentor a team of DevOps engineers, SREs, and automation specialists. Drive a culture of automation, continuous improvement, and collaboration across development and operations teams
  • Design, implement, and manage scalable, secure, and cost-effective cloud infrastructure (AWS, Azure, GCP). Oversee containerization and orchestration (Docker, Kubernetes, Helm). Establish infrastructure-as-code (IaC) best practices using Terraform, CloudFormation, or Pulumi
  • Develop and maintain CI/CD pipelines to support rapid, reliable software releases (GitHub Actions, Jenkins, GitLab CI, ArgoCD). Drive automation for deployment, monitoring, and self-healing systems. Implement observability and logging solutions (ELK, Prometheus, Grafana, Datadog)
  • Ensure DevSecOps principles are integrated into the software development lifecycle. Implement security best practices, including IAM policies, vulnerability scanning, and secrets management (Vault, AWS Secrets Manager). Maintain compliance with industry standards (SOC 2, ISO 27001, GDPR etc).
  • Define SLAs, SLOs, and SLIs for system reliability and uptime. Oversee incident management, disaster recovery, and business continuity planning. Optimize performance tuning and capacity planning for cloud infrastructure.
  • Follow information security policies and practices and keep security top of mind in all aspects of work
Desired Qualifications
  • Certifications (AWS Certified DevOps Engineer, Kubernetes Administrator, etc.)
  • Experience in high-availability, large-scale environments
  • Hands-on experience
  • Experience in machine learning infrastructure is a plus

About the company

PortPro provides a software-as-a-service transportation management system (TMS) tailored for container drayage carriers. Its flagship product, drayOS, helps carriers manage shipments more efficiently by offering AI-based order entry, real-time container tracking, appointment setting, and customer messaging through a user-friendly web interface. The platform includes a customer portal so shippers can communicate with carriers and receive updates. PortPro monetizes through subscription fees and optional premium services such as enhanced support and training. By focusing on drayage-specific workflows and seamless implementation, PortPro differentiates itself from broader TMS vendors and aims to become the go-to TMS provider for drayage carriers.

Company Size

51-200

Company Stage

Series A

Total Funding

$12M

Headquarters

Jersey City, New Jersey

Founded

2019

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Simplify's Take

What believers are saying

  • PortPro launched AI Agents on August 17, 2026, automating dispatch, billing, and compliance.
  • Inc. ranked PortPro No. 20 on Northeast fastest-growing companies on April 21, 2026.
  • Bloomberg's August 25, 2026 coverage spotlights margin gains from lower deadhead and faster invoicing.

What critics are saying

  • G2 reviews in 2026 still cite inaccurate tracking, broken integrations, and weak support.
  • PortPro's last known funding closed in January 2023, limiting firepower against larger rivals.
  • If Magaya, McLeod, or Descartes internalize drayage modules, PortPro becomes a feature.

What makes PortPro unique

  • PortPro embeds AI agents inside drayage workflows, not standalone copilots.
  • Magaya integrated PortPro on June 18, 2026, validating its execution-network position.
  • PortPro specializes narrowly in container drayage, with workflows built around ports and chassis.

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Benefits

Professional Development Budget

Flexible Work Hours

Growth & Insights and Company News

Headcount

6 month growth

5%

1 year growth

31%

2 year growth

34%
Magaya
Jun 18th, 2026
Magaya and PortPro launch integration to streamline drayage execution workflows.

Magaya and PortPro launch integration to streamline drayage execution workflows. MIAMI, FL - June 18, 2026 - Magaya Corporation, the leading freight management platform for freight forwarders and customs brokers, today announced a new integration with PortPro, the largest drayage and intermodal transportation management system in North America. The integration connects Magaya Supply Chain directly to PortPro's drayage TMS, helping freight forwarders and customs brokers streamline container execution workflows while reducing manual data entry between systems. Shipments managed in Magaya automatically flow into PortPro for dispatch and execution, while status updates, tracking information, invoices, and shipment documents flow back into Magaya in real time. According to Matt Hayden, Director of Logistics Solutions at WM Stone Logistics, the integration helps eliminate operational friction between freight forwarding and drayage execution workflows. "The PortPro integration for Magaya Supply Chain saves our team at least 15 minutes per shipment. Before the integration, teams often had to re-key shipment information or rely on disconnected handoffs between systems," said Hayden. "Now, a shipment booked in Magaya flows directly into PortPro for execution, while tracking updates, billing information, and documents flow back automatically. It creates a much smoother experience for our operators and gives customers better visibility throughout the shipment lifecycle." Built through Magaya Connect, the integration enables customers to connect the two systems without the need for custom development projects or additional software. Shipment information entered into Magaya can be tendered directly into PortPro for drayage execution, while operational updates automatically synchronize back into Magaya Supply Chain. "Freight forwarders shouldn't have to rely on emails, disparate systems, and duplicate entry just to coordinate drayage operations," said Mark Buman, Chief Revenue Officer at Magaya. "By connecting Magaya with PortPro, we're helping customers create a more connected operational workflow with greater visibility, faster execution, and less manual work across container transportation processes." Key benefits include: - One booking with no double entry between freight forwarding and drayage workflows - Real-time container status updates and tracking visibility pushed automatically into Magaya - Connected invoices and shipment documents synchronized across both systems - Secure, permission-based API connectivity with carrier-controlled data sharing - A more centralized operational workflow for container transportation execution According to Toni Pisano, Chief Operating Officer at PortPro, the partnership reflects a shared focus on helping logistics providers simplify operations while improving visibility and execution speed. "Drayage is one of the most operationally demanding parts of the supply chain, and disconnected systems only make that more difficult," said Pisano. "By integrating PortPro with Magaya, we're helping freight forwarders and brokers create a more seamless experience between shipment management and drayage execution while reducing manual work for their teams. At the same time, we're making it easier for freight forwarders to work directly with the highly performant drayage carriers operating on PortPro, helping create stronger connections between freight demand and carrier capacity." Together, Magaya and PortPro are helping freight forwarders and customs brokers create a more connected container transportation workflow, reducing operational friction while improving visibility, execution speed, and customer service across drayage operations. About Magaya Magaya, the number one freight management platform for logistics service providers, is Moving Freight Forward with a Digital Freight Platform that optimizes the entire origin-to-destination supply chain through flexible, interoperable, and modular cloud-based software. Whether used together as an integrated suite or independently, Magaya solutions enable businesses of all sizes to simplify complex logistics processes, enhance the customer experience, and grow revenues alongside profits. At Magaya, Magaya Corporation is passionately devoted to its customers' success and don't hesitate to go the extra mile. There are no limits to your growth with Magaya. Visit magaya.com to learn more. About PortPro PortPro is the largest drayage and intermodal transportation management system in North America, helping drayage carriers modernize operations through a cloud-based platform purpose-built for container transportation workflows. PortPro provides tools for dispatch, driver management, container tracking, billing, customer visibility, and operational automation, helping transportation providers improve efficiency and deliver a better customer experience. Learn more at portpro.io.

AsiaShift
May 12th, 2025
AI Meets Drayage: PortPro Launches AI Agents at a Critical Moment for the Industry

To help address these challenges, PortPro today announced the launch of AI Agents - digital tools that can think, learn, and take actions on behalf of users.

PRUnderground
Nov 22nd, 2024
PortPro Ranks #84 of the Fastest-Growing Companies in North America on Deloitte Technology's Fast 500(TM)

PortPro ranks #84 of the fastest-growing companies in North America on Deloitte Technology's Fast 500(TM).

DC Velocity
Jun 5th, 2024
PortPro Launches First-Ever Drayage TMS with an Embedded Email Inbox

(Jersey City, New Jersey and Los Angeles, California - June 5, 2024) - PortPro, the premier transportation software provider for the drayage industry, today announced the launch of a first-of-its-kind Embedded Email Inbox feature for drayage carriers and brokers looking to better command and control their operations by better managing their inboxes, improving operational efficiency and teamworkflows, and strengthening customer communications.

Transport Topics
Mar 15th, 2024
PortPro Launches TMS for Drayage Carriers and Brokers

PortPro also has introduced PortPro for Drayage Brokers, a web-based system tailored to non-asset drayage brokerages that broker loads to different drayage trucking companies.