5-7 years of experience in a leadership role within AI or technology sectors.
Strong customer engagement skills with a focus on building relationships.
Proven ability to communicate effectively with both technical and non-technical audiences.
Demonstrated strategic problem-solving skills in ambiguous environments.
Hands-on leadership style that balances high standards with empathy.
Technical proficiency in understanding APIs, data models, and system architecture.
Degree in Computer Science, Engineering, Mathematics, or related field, or equivalent experience.
Responsibilities
Lead the Agent Development Life Cycle, ensuring timely launches and customer satisfaction.
Build and manage a team of strategists, defining success metrics and growth strategies.
Act as a strategic advisor to enterprise leaders, shaping AI strategies that align with their business goals.
Guide daily delivery with customer teams, troubleshooting issues and maintaining project timelines.
Influence the evolution of Sierra's core platform based on customer feedback and unmet needs.
Benefits
Unlimited paid time off for work-life balance.
Comprehensive medical, dental, and vision coverage for employees and families.
Life insurance and disability benefits for added security.
Retirement plan options based on country of employment.
Generous parental leave policy.
Fertility and family building support through Carrot.
Complimentary lunch and snacks to keep you energized.
Discretionary stipend for personal benefit spending.
Unique opportunity for free alphorn lessons.
Full Job Description
What you'll do
Lead the Agent Development Life Cycle. Our leads operate as ICs for their first 2-4 months at Sierra, then evolve into the lead role, all while continuing to take agents from initial scope through conversation design, tooling, evaluation, launch, and continuous iteration in production. You'll both build directly and guide your team through the full lifecycle, coaching strategists to set and maintain the standard for ADLC best practices. You'll ensure agents launch on time, meet customer needs, and measurably move the customer's business.
Build the team as you build the business. You'll take on two kinds of leadership: serving as the senior sponsor on our key customer deployments, and managing a team of strategists. You'll drive how the strategist function grows, from hiring and onboarding to defining what success looks like.
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 actively build/shape the AI strategy that gets them there. You'll develop your team to do the same.
Guide delivery with the customer's working teams day to day. Run working sessions, troubleshoot agents as issues come up, and coach your team to make the calls that keep every build on track for launch. You'll be accountable for delivery quality and customer impact across your team's portfolio.
Shape the future of the product. Your team's direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prioritize initiatives, and collaborate with research, product, and platform teams to influence where Sierra goes next.
What you'll bring
Customer obsession. Genuine energy being in front of customers, understanding their business and needs, thriving in complex organizations, and building trusted relationships, plus the ability to develop that muscle in others.
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 guide teams through fast-changing, ambiguous environments.
A leadership style that comes from being hands-on. You blend high standards with empathy, fostering both speed and quality across your team.
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, as well as leading teams that run, multiple complex, high-visibility projects at once and driving them to outcomes.
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.
Even better...
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.
Background as a founder, product or strategy leader, or startup operator with high ownership and urgency.
Experience managing teams in product, consulting, solutions, or other customer-facing roles.
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
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
About Sierra Club
The Sierra Club is a nonprofit organization that promotes environmental conservation. It was founded in 1892 by John Muir and is one of the oldest and largest environmental organizations in the United States. The organization has over 3.8 million members and supporters and is dedicated to protecting the planet's natural resources and wildlife. The Sierra Club engages in a variety of activities, including lobbying for environmental legislation, organizing outdoor activities, and publishing a magazine. The organization is headquartered in Oakland, California.
