$12 trillion in goods move by freight every year, coordinated by people copy-pasting between email and spreadsheets. We’re building the AI that changes that.

About Sidecar

Sidecar is an AI workplace software for freight forwarding. Our AI agent sits on a forwarder’s inbox, reads every quote request, extracts shipping details from emails and PDFs, drafts professional responses, and triggers workflows across carriers and ERPs, all in seconds. What used to take a sales rep 30+ minutes per email now takes under a minute with human review.

We believe the smartest logistics companies of 2030 will be run by 10 people with AI, not 100 people with spreadsheets. We’re building the software that makes that possible.

We are backed by leading Silicon Valley VCs, angel investors, and industry advisors.

The Role

You’ll own customer deployments end-to-end and build the implementation playbook to take us from 10 customers to 30.

What You’ll Do

1. Own customer implementations end-to-end: from signed contract through go-live and beyond. You drive the timeline, engineering drives the build.

2. Plan and execute AI agent deployments at enterprise freight forwarders: phasing rollouts, defining go-live criteria, and managing proof-of-value engagements.

3. Build repeatable implementation playbooks: so onboarding customer #30 takes weeks, not months.

4. Run 5–8 concurrent implementations without dropping context: managing timelines, engineering workstreams, and customer stakeholders across all of them.

5. Drive go-live readiness decisions: defining the metrics, checks, and sign-offs needed before AI touches a customer’s live email workflow.

6. Manage stakeholder communication across customers, engineering, and founders.

What We’re Looking For

1. 1+ years in project management, program management, or technical operations at a tech startup. You’ve shipped, not just planned.

2. You’ve managed technical deployments. Not generic rollouts: implementations where the product touches customer data, integrates with their systems, and requires testing before go-live.

3. You’re AI-literate. You use Claude, ChatGPT, or similar tools daily because they make you faster. You understand what AI can and can’t do.

4. You move fast and have been recognized for it. Promoted early, took on scope beyond your title, or built something from zero.

5. Bangalore-based, in-office.

Nice to Have

• Experience in logistics, freight forwarding, or supply chain

• Experience deploying AI/ML products at enterprise customers

• Startup experience (Series A or earlier)

• Familiarity with Linear, Notion, and modern PM tooling

Benefits

• Compensation: top-bracket salary and high equity (meaningful ESOPs, not symbolic)

• Meals: lunch and dinner at the office + unlimited snacks, coffee, and energy drinks

• Wellness: annual gym / wellness reimbursement

• Health: comprehensive health insurance