Job Description
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What you'll do
Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
What you'll bring
8-10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication.
Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
Even better...
Familiarity with the AI landscape, key players, and emerging trends.
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Sierra
View Company ProfileSierra (operating under sierra.ai, legally Sierra Technologies, Inc.) is the premier, enterprise-grade autonomous AI agent platform, conversational intelligence pioneer, and generative AI orchestration powerhouse engineered to act as the definitive, brand-aligned customer experience and transaction resolution layer for global enterprises. Co-founded in 2023 by tech luminaries Bret Taylor (former co-CEO of Salesforce, CTO of Facebook, and Chairman of the Board at OpenAI) and Clay Bavor (former Google Vice President leading Google Workspace and AR/VR initiatives), the company completely eliminates the severe limitations of traditional conversational bots—where legacy chat setups rely on static decision-trees, struggle with open-ended natural language, and fail to carry out real, multi-step back-office transactions—by deploying a sophisticated, enterprise-ready Agent OS. Moving far beyond passive FAQ responders or basic keyword matching widgets, Sierra natively unifies deep, multi-turn reasoning engines, strict goal-oriented behavior scripting, real-time enterprise system-of-record integrations (such as Salesforce, Shopify, and Zendesk), and active policy governance modules into a high-availability, compliance-first platform. Operating with massive commercial velocity, its brand-native AI agents are trusted by household names like Sonos, SiriusXM, WeightWatchers, ADT, Casper, and Chubbies to handle complex customer support, billing inquiries, and service modifications autonomously. Highlighting its category-defining momentum and meteoric growth trajectory, the company closed a monumental $950 million Series E financing round in May 2026 led by Tiger Global and Google's GV, with heavy-tier participation from Sequoia Capital, Benchmark, Thrive Capital, and Greenoaks Capital, catapulting its market valuation to an astronomical $15.8 billion. Under the hood, its technology core utilizes its proprietary \"Constellation\" architecture—a multi-layered model structure that leverages a primary LLM (utilizing models from OpenAI, Anthropic, and Meta) paired with secondary supervisor models to monitor response appropriateness—designed to execute complex API transactions with millisecond-level orchestration latency. What sets Sierra apart is its uncompromising dedication to replacing fragile, script-bound chatbots with absolute conversational predictability, dynamic transaction resolution, and rigorous data compliance (SOC 2, HIPAA, GDPR, and CCPA); by bridging the gap between performance-intensive frontier model intelligence and high-level enterprise business logic, the company remains a definitive cornerstone of modern algorithmic customer operations and global generative AI transformation.
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