Shackleton AI Comes Out of Stealth With $5 Million to Put AI Agents on the Construction Site. What New York Builders Should Know
New York-based Shackleton AI raised a $5 million seed round led by Battery Ventures for an 'agentic operating system' that automates the paperwork of construction projects. Here's what the company says it does, who is backing it, and what contractors and developers should ask before handing admin work to AI.
NEW YORK — Ask anyone who has run a construction job what eats their week, and the answer is rarely the building. It’s the RFIs, the submittals, the budget reconciliations and the status updates scattered across half a dozen apps. A new New York startup is betting that AI agents can take that work off project managers’ desks.
Shackleton AI emerged from stealth on Nov. 4 and announced a $5 million seed round led by Battery Ventures. Brick & Mortar Ventures, Trust Ventures, Correlation Ventures, Motivate Partners, Thayer Investment Partners, Act One Ventures, Brainstorm Ventures and Silence VC also participated, according to the company’s announcement. Shackleton says it will use the money to expand the workflows its AI agents can handle and to speed up its go-to-market push.
Builders Building for Builders
The founding story is a familiar one in vertical software: operators who got fed up with their own tools. Shackleton’s co-founders, Michael Ragheb, Hassan Yasin and Olexandr Kaltsev, previously grew Ernest, a tech-enabled commercial general contractor, to $35 million in revenue across the Southeastern United States, the company says.
“I was spending more time moving data between systems than running my jobs at Ernest,” Ragheb, Shackleton’s co-founder and CEO, said in the release. “Every hour a project manager spends chasing status across disconnected tools is margin lost.”
The company was founded in 2026 and is headquartered in New York. Its platform launched in June, and Shackleton says it now manages more than $1 billion in project value across more than 15 states. Customers named in the announcement include midsize general contractors working in multifamily, industrial and commercial construction, plus multi-location brands Red Lobster, Dog Haus and Pepper Lunch.
What the Product Actually Does
Shackleton describes itself as an “agentic operating system for development and construction.” In plain terms, it is trying to put the whole project lifecycle, from site selection and bidding through turnover, into one system, then let AI agents do the administrative follow-through.
According to the company, those agents can:
- Draft requests for information (RFIs)
- Follow up on overdue submittals
- Flag budget variances before payment requests go out for approval
- Turn field notes into daily reports
The pitch against existing construction software is that legacy platforms were built mainly as systems of record, leaving people to chase the follow-ups. Shackleton says its agents work across the entire platform rather than inside a single app, and that human review and approval workflows remain in place.
The company’s framing of the problem: construction firms commonly juggle seven to 10 systems, and teams can spend 10 to 15 hours a week on data entry and admin work. Those are Shackleton’s figures, not independent research.
Shackleton also claims that multi-location customers have finished buildouts up to 35% ahead of schedule and as much as 18% under budget. Those are company-reported best-case results, and the release doesn’t say how many projects they reflect.
Why Investors Are Interested
“Construction is one of the largest and least digitized sectors in the economy, and the teams running these projects are buried in manual work that software should have automated a decade ago,” said Michael Brown, a general partner at Battery Ventures, in the announcement.
The round fits a pattern we’ve been tracking all fall: New York investors and founders are pouring money into AI agents built for one specific industry rather than general-purpose assistants. In just the past few weeks we’ve covered Clark, which builds AI audit staff for CPA firms, and Mostest, which automates event booking for restaurants and hotels. Shackleton brings that playbook to the job site.
It also lands at a busy moment for the city’s builders. On Nov. 3, New York City voters approved a charter amendment directing the Department of Buildings to develop a central permitting hub that brings together 40 permits and approvals now handled by 18 agencies and offices, with a target launch of Dec. 1, 2029. Less paperwork with the city and less paperwork inside the project are two halves of the same complaint.
Questions to Ask Before You Hand Admin Work to an AI Agent
For New York general contractors, developers and franchise operators managing buildouts, tools like this are worth a look. They’re also worth testing hard. Some practical questions:
- Who signs off? Shackleton says human approval stays in the loop. Confirm exactly which actions, like sending an RFI to an architect or flagging a pay app, need a person to click “approve.”
- What happens to your existing systems? “One platform” can mean migrating years of project data. Ask what imports cleanly and what doesn’t.
- How are errors caught? A draft RFI with a wrong spec reference costs time. Ask for an audit trail of what agents did and why.
- Can you pilot on one job? A single project with a willing PM is the cheapest way to check whether the promised hours come back.
- Who owns the data? Bids, budgets and subcontractor pricing are competitive information. Read the contract.
Shackleton is taking demo requests on its website. Whether agentic software becomes standard in construction is still an open question, but it’s one New York builders will be hearing a lot more about.