ストラテジスト (Strategist, Agent Development)

What you’ll do:

As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.

• Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.

• Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.

• Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.

• Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.

Example projects

These are the kinds of projects that strategists on our team have worked on recently:

• Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.

• Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.

• Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.

• Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.

• Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.

What you’ll bring

• Outstanding Japanese Communication Skills: Excellent Japanese verbal and written communication skills for enterprise business settings, with the ability to convey complex technical concepts to non-technical stakeholders, foster collaboration, and drive projects forward with clarity.

• Client-Facing Consulting Experience: Whether in AI, digital transformation, or business strategy, experience engaging directly with customers to understand their needs and translate ideas into concrete solutions. Proven ability to lead proof-of-concepts (POCs) and ideally convert them into long-term engagements that drive sustainable value creation.

• Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.

• Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.

• Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.

Even better

• Business-level English Communication Skills: Experience working in an international company where English is the primary language of communication; native or business-level proficiency in English.

• Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.

• You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.

• A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.

Interview Process

• Interviews are primarily conducted in Japanese.