Strategist, Agent Development - Flagship Deployment

What you’ll do

As an Agent Strategist on a Flagship Deployment, you’ll lead the end-to-end deployment for one of Sierra’s largest and most strategic customers. You own how Sierra's AI agents come to life, often managing scaled deployments as well as new proofs of concept within the same account. 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 and executives day to day. Oversee overall program management while ensuring ongoing executive alignment on the long term roadmap.

• Navigate enterprise complexity with cross-functional teams (engineering and product). At this scale, every big technical discussion is also a negotiation — you'll need to read the implications in real time, hold your ground, and steer toward the right outcome. Expect to work across business units, procurement, compliance, and senior execs.

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

• Manage internal resourcing requirements. Ensure that your deployment is appropriately resourced today and into the future

• Drive financial success for both the customer and Sierra. Ensure value exchange is optimized, drive revenue upside for Sierra, and work internally to manage down cost to serve over time, improving margins.

• Partner with Sales on commercial strategy. You are a key player in closing new business within the deployment by identifying opportunities, aligning resources, and

Example projects

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

• Plan, organize, and execute on-site business reviews onsite at a Fortune 100 company with Sierra cofounders in attendance

• Manage a portfolio of agents across a customer deployment as they scale nationally, to new use cases, and grow in technical complexity

• Build relationships throughout the customer’s organization, unlocking high trust, social capital, and ultimately new ARR

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

• 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

• Proven track record: 10+ years of relevant experience driving results in high stakes situations in an enterprise customer facing role, ideally in a dedicated, embedded model with a named enterprise account — you know what it means to be accountable for a relationship at that depth.

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

• Communication. Clear, direct, and persuasive across technical and non-technical audiences.

• 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.

• Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.

Even better...

• You've run a company, business unit, forward deployed team, or have comparable experience in general management of business initiatives that require technical aptitude, strategic leadership, operational excellence, and financial outcome accountability.

• 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.

• 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.

Our values

• Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.

• Flexible (unlimited) paid time off

• Life insurance and disability benefits

• Retirement plan dependent on country of employment

• Parental leave

• Fertility and family building benefits through Carrot

• Free alphorn lessons