Forward Deployed Strategist

About Chalk

Chalk (chalk.ai) is the platform for production AI. Trusted by enterprises including Whatnot, Grindr, Mission Lane, Turo, and Apartment List, Chalk brings together context, runtime, and learning for agents and models. Chalk’s Context Engine delivers live context by querying data across warehouses, databases, streams, and APIs, straight from the source. Chalk’s runtime powers agents and models with infrastructure and governed access to LLMs and tools. Together, these capabilities help teams build AI that understands their business, continuously improves, and runs reliably in production. We’ve recently raised a $50 million Series A, led by Felicis. Learn more at chalk.ai.

About The Role

Chalk is the AI data platform built for inference. Customers come to us for two halves of the same problem: the context their models and agents run on, and the runtime they run in. Both sit inside the customer’s own cloud. Forward Deployed Strategists own the technical direction of Chalk’s integrations: what gets built, in what order, and whether it holds up. You sit alongside sales, delivery, account management, and support on your accounts, and you’re the technical judge across all of it. You’ll work closely with FDEs, who build directly with customer engineering teams. Some of that work is model-driven: fraud, payments, underwriting, recommendations, pricing. Increasingly it is agentic. Investigation agents that sit alongside data scientists, workflow automation, trust and safety, customer support, all of it running against real production context inside the customer’s own environment. Most problems start with the customer’s architecture rather than ours. You will be asked to weigh in on systems Chalk does not touch. The bar for this role is architectural depth and judgment.

What you will do

• Run technical discovery: get inside how a customer's systems work, what is breaking, and what they are trying to ship.
• Advise on their architecture and their plans, including the migration path off whatever they run today. Tell them plainly what will break, what to sequence first, and what is not worth doing.
• Design what they build on Chalk, and set the bar it has to clear on correctness, latency, and cost.
• Design agentic solutions on Chalk: what an agent is allowed to reach, how it gets evaluated against real production context before it ships, and how it runs safely inside the customer’s own cloud.
• Design, scope, and execute tight POCs. Pick the one thing worth proving, define what a clean result looks like before anyone starts, and keep the scope from drifting.
• Answer the questions a customer's principal engineers ask in week three.
• Partner with sales on the accounts where the decision is being made.
• Find the work worth doing next, and judge honestly whether it is a fit.
• Break work into projects with clear owners and dates, and hand the deep build work to the delivery engineers who will do it.
• Work with account management and support to keep the technical direction of an account coherent once it is live.
• Take what you learn in the field back to product and engineering, and argue for the changes that matter.

What we're looking for

• Real depth in production infrastructure, and a feel for how systems carrying live traffic actually fail.
• You have advised engineering teams on systems you did not build, and they took the advice.
• Technical taste. You have opinions about how systems should be built and you can defend them against people who have opinions of their own.
• You know how to scope a POC that proves the thing and nothing else, and you have said no to the ones that were never going to prove anything.
• Strong Python and SQL. You build prototypes and reference implementations, and you can read a customer's codebase and hold a conversation about it.
• Willing to tell a customer the thing they do not want to hear, including that a plan of theirs is wrong.
• You work well across a team. This role only functions if sales, delivery, account management, and support all trust your read.
• Excellent written and verbal communication, problem-solving, storytelling, and analytical skills.

Bonus points

• All optional. None of these are required.
• Experience deploying software into a customer's own cloud.
• Experience getting AI agents to run reliably against real production systems and real data.
• Domain depth in fraud, payments, underwriting, identity, recommendations, pricing, or logistics.
• Rust or C++.

Compensation

Actual compensation awarded to successful candidates will be based on several factors, including individual qualifications objectively assessed during the interview process. Our comprehensive total package plays a major role in how we recognize individuals for the impact they will have on Chalk’s growth and us achieving our goals. Chalk offers early team member equity and competitive benefits package in addition to the cash compensation.

Inclusivity

Chalk is an equal opportunity employer. We value diversity and inclusion and provide reasonable accommodations to anyone in need of individualized support.