The Opportunity

Commercial construction is a $2.4T industry still run on spreadsheets, WhatsApp threads, and gut instinct. Shackleton is changing that, building the first AI operating system for commercial general contractors and automating everything from bid management to field execution to financial close.

We know this industry because we have lived it. Our founding team built and scaled Ernest, a self-performing general contractor, to $30M ARR before building Shackleton on top of what we learned. That operator credibility is our unfair advantage, and it is why we win.

We closed our seed round led by Battery Ventures with participation from Trust Ventures, Correlation Ventures, Brick and Mortar Ventures, Act One Ventures, Motivate Partners, Brainstorm VC, and Thayer. Now we are hiring an AI Onboarding and Ops Manager to own how construction companies get live on Shackleton AI.

The Role

This is not a traditional onboarding seat where you follow a static checklist. Shackleton is an AI product, and you will use AI heavily every day - to configure client workflows, automate customer onboarding and training, automate feature requests, and troubleshoot in real time. You will onboard customers onto Shackleton AI, translating their existing processes into our platform, using AI to automate as much of these workflows as possible and move faster than a traditional onboarding team ever could.

What you will own:

- Own the end-to-end onboarding experience — from kickoff through go-live and early adoption for all customers
- Leverage AI to build an automated onboarding and support functionality to support scale
- Translate a client's current processes (bidding, PM, field, finance) into Shackleton workflows
- Run onboarding calls and training sessions across stakeholder types (owners, PMs, field, finance/bidding teams)
- Build and maintain reusable onboarding assets, continuously improving them using AI




- Develop PRDs to detail and communicate feature requests with product and engineering
- Manage multiple client onboardings concurrently while maintaining a high bar for documentation

What We Are Looking For

Background

- Daily, hands-on fluency with AI tools - this is not optional, you will use AI constantly
- 3-5 years in customer onboarding, implementation, or customer success, ideally at a SaaS company
- Bonus experience working with SMB customers
- Track record of building or improving onboarding processes, not just executing a fixed playbook
- Comfortable managing multiple concurrent client relationships
- Construction or proptech experience is a plus, not a requirement — we will teach the domain

Who you are

- Owner - you treat every onboarding as if the outcome is entirely on you. You don't wait for a playbook; you identify what isn't working, fix it, and bring the result back to the team.
- High Quality Bar - your documentation and configurations don't need to be cleaned up by someone else before a client sees them. Moving fast doesn't mean shipping mediocre work.
- Whatever it Takes to Win - when an onboarding hits a wall, you figure it out and don't leave the job half-done, without cutting corners or burning out the client relationship.
- Team Player - you communicate early when something's off, ask for help before you're underwater, and share context that makes the team sharper.
- AI-Native - you already default to AI tools to move faster and are always looking for the next task to automate.

Why Now Construction has been one of the last major industries to see meaningful software adoption. That is changing rapid. We are at the beginning of a multi-decade shift, we have the operator credibility to win trust in a relationship-driven market, and we are hiring the person who will build the revenue engine from the ground up.

If you live inside AI tools, love turning messy client processes into clean systems, and want to build something - this is the seat.

📌 AI Onboarding and Ops Manager (Toronto)
🏢 Shackleton AI
📍 Toronto