Enterprise Sales Leader

About us Sierra 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 Sierra, 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. About the Healthcare team Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. Join us to transform the patient experience across the healthcare system—and help build technol

About us Sierra 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 Sierra, 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. About the Retail team Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. Join us to transform how the world’

About us Sierra 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 Sierra, 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. About the Consumer Business Services team Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business. This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer

We are searching for an experienced Regional Vice President, Sales, US State and Local that has a passion for technology and a solid track record in second line leadership working in a high growth tech environment. As we continue to establish contract presence, local relationships and influence, and break into bigger deals, and formalize our support for the larger SLED segment, this sales department within Datadog will blaze the path for the organization's growth. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Lead a team of first line managers; building, developing and training enterprise teams Drive a team to sales quota attainment on a quarterly and yearly basis Develop and execute a high-growth strategy to increase customer acquisition Continuously evaluate the sales process, finding sales processes to break into new markets and expand current markets Maintain and develop team forecasts Who You Are: Experienced in managing a high performing Enterprise Sales Leadership team for a B2B technology company A proven Sales professional with 5+ years of overall Enterprise Sales experience, building relationships with Fortune 1000 companies and managing complex sales processes Motivated by leading a sales team, setting quotas and managing your team against those quotas Passionate about coaching others with a successful track record as an individual contributor and can share relevant and complex closing experience with a growing team Strong in your communication and relationship-building skills with a track record of developing loyal and satisfied customers Determined to meet and exceed forecasts with a history of success Comfortable and resilient in a fast paced environment with strong attention to detail Datadog values people from all walks of life. W

What we're building Mutiny is the self-improving AI infrastructure for GTM teams to execute faster and close more revenue. Our ambition is to do for revenue velocity what Cursor and Claude Code did for engineering velocity. With Mutiny, everyone in sales and marketing gets a bench of GTM athletes that handle any work across their revenue motion and learn from what's actually moved their deals. In April we re-launched the product as an agent-first platform. Anthropic showcased us as a leader in AI GTM. MRR is growing more than 70% month-over-month, with customers like Uber, Rippling, and Snowflake. We're backed by Sequoia, YC, and Insight, and we're building a generational company. The opportunity Most sales leaders inherit a playbook. You'll write one. As a founding first sales manager, you'll partner with the founders, own the number end-to-end from first conversation to expansion, and use AI and our own product to build a team of full-stack sellers that outsells teams 5x their size. What works for our team becomes what works for every sales team running on Mutiny. The calls you make on hiring, motion, and product feedback will shape the company well beyond the sales org. This role is in person in New York City, five days a week. What you'll own Revenue. Sales-led revenue, end-to-end. Pipeline, conversion, ARR, retention, and expansion. The number is yours. PLG to enterprise. Define qualification, build the enterprise pipeline, and turn self-serve signups at companies like Rippling, Uber, Snowflake, Zendesk, and Gusto into seven-figure deals. Outbound. Generate net new meetings with the hottest AI companies and enterprises in the market. Build the motion, run it yourself first, then teach it. The team. Hire, coach, and develop a team of Account Executives into top performers. The ceiling on revenue is the ceiling on the team you build. The playbook. Write the sales motion that becomes the default for every team running on Mutiny. What works here ships to thousands

About the Role As a Sales Manager, Energy, you will build and lead a team of Account Directors focused on strategic growth across utilities, oil and gas, renewables, power generation, and energy services. The team will partner with complex organizations modernizing operations, improving reliability, accelerating the energy transition, and adopting enterprise AI responsibly at scale. You’ll help the team navigate regulated enterprise sales cycles, deepen relationships with business, technology, operations, engineering, security, and risk leaders, and drive adoption of OpenAI’s platform across safety-conscious, asset-intensive organizations. Key Responsibilities Recruit, develop, and lead a high-performing team of Energy Account Directors. Create a strong coaching culture through deal reviews, account strategy sessions, ride-alongs, and structured 1:1s. Define the Energy GTM strategy, including subsector segmentation, account prioritization, partner strategy, executive engagement, and territory planning. Drive disciplined pipeline generation, forecast accuracy, and operational rigor. Guide multi-stakeholder opportunities involving operations, engineering, digital, data, security, legal, risk, procurement, and executive leadership. Help customers translate AI and API capabilities into measurable outcomes across asset and field operations, grid and generation planning, engineering knowledge, customer service, commercial workflows, and enterprise productivity. Partner with Product, Solutions Architecture, Technical Success, Legal, Security, Finance, and policy experts to support responsible deployment. Provide structured feedback on customer requirements, integration blockers, reliability and governance needs, and emerging industry trends. What We’re Looking For 15+ years of enterprise sales, GTM, or sales leadership experience. Proven experience building and scaling enterprise sales teams responsible for complex strategic accounts and large revenue targets. Deep underst