Strategist, Agent Development - Flagship Deployment

United States Digital Space LLC; San Francisco (CA); On-site; USD 180,000 - 250,000; Full time

Benefits offered by this job

Unlimited PTO

Medical benefits

Dental benefits

Vision benefits

Life insurance

Retirement plan

Job summary

Sierra is seeking an Agent Strategist to lead end-to-end deployments for flagship enterprise customers, translating business goals into scalable AI agent solutions. You will work at the intersection of product, engineering, and client leadership to deliver high-impact outcomes.

You will own the deployment lifecycle, guide strategic AI direction, and partner across teams to optimize value while driving revenue growth and efficiency for both client and company.

Qualifications

• 10+ years of enterprise, customer-facing experience.
• Proven ability to drive outcomes in high-stakes environments.
• Experience guiding executive-level stakeholders and cross-functional teams.

Responsibilities

• Own the end-to-end deployment lifecycle for flagship customer deployments.
• Advise enterprise leaders and shape AI strategy.
• Coordinate cross-functional teams including engineering and product.
• Drive program management and executive alignment on roadmaps.
• Directly impact product by surfacing unmet needs to research and platform.
• Manage internal resourcing to ensure deployments are funded today and tomorrow.
• Partner with Sales on commercial strategy and opportunities.

Skills

Customer obsession

Communication

Strategic problem-solving

Technical aptitude

Ownership and delivery

Enterprise experience

Education

Degree in Computer Science, Engineering, Mathematics, or MBA

Job description

About usSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding the company, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

What you’ll do

As an Agent Strategist on a Flagship Deployment, you’ll lead the end-to-end deployment for one of the company’s largest and most strategic customers. You own how the company'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 the company 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 the company. Ensure value exchange is optimized, drive revenue upside for the company, 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 the company 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‑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.

• Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.

• Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self‑reflect to continuously self‑improve.

• Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.

• Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.

What we offer

We want our benefits to reflect our values and offer the following to full-time employees:

• Flexible (unlimited) paid time off

• Medical, dental, and vision benefits for you and your family

• Life insurance and disability benefits

• Retirement plan dependent on country of employment

• P