Website:
usesidecar.com
Job details:
We're hiring our first Project Manager at Sidecar.
$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.
The Role
- You'll be our first project manager. Today, customer implementations run on founder-led Slack threads, Linear tickets, and ad-hoc status calls. It works, but it doesn't scale.
- You'll own customer deployments end-to-end and build the implementation playbook that takes us from 5 customers to 30. Engineering builds. You drive.
What you'll do
- Own customer implementations end-to-end, from signed contract through go-live and beyond. Phase the rollout, define "ready," manage the proof-of-value.
- Plan and execute AI agent deployments at enterprise freight forwarders, data collection, SOP documentation, model calibration, staged production rollout.
- Run 5–8 concurrent implementations without dropping context, managing timelines, engineering workstreams, and customer stakeholders across all of them.
- Drive go-live readiness decisions, define the metrics, checks, and sign-offs needed before AI touches a customer's live email workflow. Say no when the numbers aren't there.
- Daily health check — open the KPI dashboard every morning, check processing funnel, detection rates, routing accuracy, rejection rates. Spot anomalies before the customer does.
- Run weekly customer calls and Daily Status Reports, metrics, missing data items, open issues, next steps. You are the single point of contact.
- Build the implementation playbook so onboarding customer #30 takes weeks, not months.
- Close the feedback loop to product, surface patterns from customer conversations so engineering and product prioritize the right things.
What we're looking for
- 1+ years in project management, program management, implementation, or technical operations at a tech startup. You've shipped, not just planned.
- You've managed technical deployments: Implementations where the product touches customer data, integrates with their systems, and requires testing before go-live. You can read a KPI dashboard, understand what "11.3% send rate" means, and dig into the data when something looks off.
- You're technically fluent: comfortable around APIs, dashboards, data pipelines, and AI model outputs. You can read a system log and ask the right follow-up question.
- You're AI-native: not "aware of AI," but you actually use Claude, ChatGPT, Cursor, Replit, v0, or Copilot in your daily work because it makes you work faster.
- Sharp written English. Weekly customer calls, DSRs, escalations, all in your voice.
- In-office, 996 (6 days a week). We work out of our Bangalore and San Francisco offices. this role is based in Bangalore.
Nice to have
- Experience in logistics, freight forwarding, or supply chain (we'll teach you if you don't)
- Experience deploying AI/ML products at enterprise customers
- SQL basics, enough to navigate a Metabase dashboard independently
- Series A or earlier startup experience
- Familiarity with Linear, Notion, and modern PM tooling
Benefits
- Top-bracket salary and high equity compensation (meaningful ESOPs, not symbolic)
- Lunch and dinner at the office + unlimited snacks, coffee, energy drinks
- Annual wellness benefit (gym reimbursement)
- Health Insurance
Selection process
We hire AI-native people with an AI-native process. Two steps:
- Case study: The assignment is available on our career page linked to apply. One page, 600-word hard cap, 72-hour turnaround. Four questions covering your implementation plan for a new freight-forwarder customer, go-live readiness criteria, your operating stack for running 3–5 concurrent implementations, and the #1 risk. You can (and should) use Claude, ChatGPT, Cursor - we expect it. We've already run our strongest models on this exact case and locked their answer as our internal reference. Your submission is scored against it. Submit your completed case study along with your details (name, email, phone, LinkedIn) through the form on the career page. If you beat our AI, you move to interviews.
- Interviews: A couple of rounds with the team on your judgment, your case study, and what you'd build here. Offer follows fast when we find the right person.
We are backed by leading Silicon Valley VC's, Angel Investors, and Industry Advisors, and pay top-bracket salaries alongside equity compensation. We are highly selective and believe in only hiring and retaining the best.
Click on Apply to know more.