Strategic Ai Transformation Lead in United States

About Flexport: At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission to make global commerce so easy there will be more of it. We’re shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Today, companies of all sizes—from emerging brands to Fortune 500s—use Flexport technology to move more than $19B of merchandise across 112 countries a year. The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. We are proud to have the support of the best investors in the game who believe in our mission, solutions and people. Ready to tackle global challenges that impact business, society, and the environment? Come join us. The Opportunity: We are seeking Account Executives in Salt Lake City and Phoenix with experience in end to end supply chain solutions and fulfillment to build and maintain a healthy book of business. You'll be part of a high-performing team where you’ll focus on building up Flexport’s brand while solving customer problems with tech-enabled supply chain and fulfillment solutions. A normal day might include leading a discovery call with a prospect to uncover more about their supply chain processes, project managing the complexities of a global supply chain, reviewing a customer’s growth strategy with their Flexport Operations Team, jumping on a plane and travel with a prospective client to tour a Flexport warehouse, or sharing your best practices with the broader sales team in a peer learning session. You will Build your book of business by closing net-new customers and/or cross-selling and upselling existing customers that contribute to Flexport's overall revenue goals Uncover and connect with ideal clients through a combination of self-prospecting and collaboration with our SDR team Consult with new clients to understand their supply chain needs Create a value-add

About Flexport: At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission to make global commerce so easy there will be more of it. We’re shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Today, companies of all sizes—from emerging brands to Fortune 500s—use Flexport technology to move more than $19B of merchandise across 112 countries a year. The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. We are proud to have the support of the best investors in the game who believe in our mission, solutions and people. Ready to tackle global challenges that impact business, society, and the environment? Come join us. Build and grow with us! Join Flexport as an Account Executive! This role has a robust compensation package: Base salary: $91,000-115,000; OTE: $182,000-230,000, uncapped accelerators, equity grants, competitive benefits and more. The Opportunity: We are seeking an Account Executive with experience in freight, end to end supply chain solutions and fulfillment to build and maintain a healthy book of business. You'll be part of a high-performing team where you’ll focus on building up Flexport’s brand while solving customer problems with tech-enabled supply chain and fulfillment solutions. A normal day might include leading a discovery call with a prospect to uncover more about their supply chain processes, project managing the complexities of a global supply chain, reviewing a customer’s growth strategy with their Flexport Operations Team, jumping on a plane and travel with a prospective client to tour a Flexport warehouse, or sharing your best practices with the broader sales team in a peer learning session. This role features a 50/50 compensation model (Base + Uncapped bonus), designed for high-performers to effectively maximize their earnings through a heavily ince

About Flexport: At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission to make global commerce so easy there will be more of it. We’re shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Today, companies of all sizes—from emerging brands to Fortune 500s—use Flexport technology to move more than $19B of merchandise across 112 countries a year. The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. We are proud to have the support of the best investors in the game who believe in our mission, solutions and people. Ready to tackle global challenges that impact business, society, and the environment? Come join us. The opportunity Flexport operates at the intersection of global trade, technology, and policy — which means the stories we tell matter. We're looking for a Senior Manager, PR & Communications to drive forward how Flexport shows up in the world: in the press, on our blog, across social channels, in customer inboxes, and inside the company. This is a high-visibility, high-trust role. You'll work directly with our CEO & Founder and members of the leadership team to shape Flexport's narrative and ensure we're part of the conversations that matter — from supply chain disruptions and trade policy shifts to AI innovation and the future of logistics. You'll also be the person who makes sure our customers and employees hear from us clearly, consistently, and at the right moments. This role requires someone who can toggle between crafting a pitch to a Tier 1 reporter, writing a customer email about a service change, coaching an executive before a live interview, and developing a content calendar that ties Flexport's story to the biggest themes in global commerce — all in the same week. You will Public Relations & Media Support Flexport's PR strategy end-to-end: p

We are seeking a Vice President of Marketing to lead and scale the company’s end-to-end marketing function, with a clear mandate: build a durable, performance-driven growth engine that delivers measurable business outcomes. This role sits at the center of Marketplace performance, accountable for the systems that drive acquisition, activation, and monetization across SMB and mid-market customers - and for ensuring those systems scale efficiently and predictably. We have strong foundations: a scaled marketplace, global supply, and growing demand across key AI categories. What’s needed now is a step-change in how we convert that demand into durable growth. This is a senior executive role with significant autonomy and company-wide influence. You will lead a multi-disciplinary organization and partner closely with Product, Engineering, Data Science, and Finance to improve the full customer journey. Responsibilities *Own and scale the Marketplace growth system for SMB and mid-market customers, translating company strategy into a multi-year, integrated operating plan across acquisition, activation, engagement, and monetization, with clear accountability to business outcomes such as GSV per active client and overall company growth. *Drive a step-change in how Marketing operates by scaling experimentation, improving efficiency, and building a more integrated, high-performing system across all disciplines. *Define and lead the long-term vision, strategy, and execution roadmap for Marketing, positioning the function as a core driver of gr

We’re looking for a Senior Staff Software Engineer with deep experience in GenAI/ML to join Datadog’s Application Performance Monitoring (APM) team. APM is a product which provides deep visibility into applications, enabling users to identify performance bottlenecks, troubleshoot issues, and optimize services. With distributed tracing, profiling, out-of-the-box dashboards, and seamless correlation with other telemetry data, Datadog APM provides some of the deepest and most structured visibility into the health and performance of applications. This context sets us up for an opportunity to be the world leaders in agentic investigations and incident troubleshooting. You’ll act as a technical leader within the APM group, focused on agentic workflows. You’ll lead efforts to design, train, evaluate, and deploy GenAI/ML models at scale. We’re looking for a product-minded ML engineer with strong technical expertise, excellent communication skills, and a track record of driving impactful initiatives end to end. 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: Serve as the technical owner for GenAI initiatives within APM, leading design, development, and deployment of ML/AI-powered features across multiple teams. Guide long-term strategy and technical direction for GenAI workflows across APM and related products. Build and benchmark GenAI/ML models using state-of-the-art techniques. Contribute to Datadog’s broader senior engineering community through thought leadership and collaboration on company-wide initiatives. Collaborate with cross-functional teams to build automated investigation and triaging tools. Influence product direction by bringing a strong product mindset to your work, always advocating for the end user. Guide teams through ambiguity, sc

This is a senior individual contributor role for someone who wants to actively shape how Engineering, one of the most important parts of how Datadog develops its people. You'll sit at the center of Datadog's biggest talent bets for Engineering: how we build leaders, define career paths and org design, evolve performance, move talent internally, and plan succession for our most critical roles. You’ll own this work end to end, from the first framing conversation with senior leaders through to delivering a program running at scale. AI is changing how Engineering builds software, and it is changing how People builds the programs that support Engineering too. This role sits at the centre of both: understanding how AI is reshaping engineering roles, skills and structures, and building AI-powered solutions within People to keep pace. 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: Design and lead complex talent programmes for Engineering, spanning leadership capability, career architecture, org design, performance, internal mobility and succession for critical roles. Partner directly with PBPs and senior leaders to turn ambiguous problems into clear programme goals, design principles and success measures. Help Engineering and People understand and respond to how AI is reshaping roles, skills and ways of working, and translate that shift into practical talent and org design choices. Stay hands-on from concept through to adoption: this is a build and run role, not a strategy and handover role. Work across Enablement, Learning, People Analytics and People Systems so what you build scales and embeds into core people processes. Equip PBPs with frameworks, tools and executive-ready narratives that support real adoption in the business. Operate in ambigu

The Dashboards product is Datadog's unified single-pane-of-glass for metrics, logs, and traces—a comprehensive treasure trove of observability data. We are transforming Dashboards into an AI-native control surface and the central hub where every team moves seamlessly from question to insight to action – providing a guided experience that feels like having an expert SRE at your side and ensuring the entry point is never an empty canvas. We're hiring a Staff Applied Scientist to define and guarantee the quality of this AI system at scale. "Good" isn't one number — it spans answer quality, tool-selection accuracy (critical given the growing catalog of data sources and visualizations), retrieval relevance, latency, token cost, and end-to-end agent success. The space is full of open questions. How do you evaluate an agent end-to-end when the trajectory is non-deterministic? How do you score tool selection when a user’s query can result in the agent making decisions against dozens of visualizations and data sources – both of which are growing month over month? How do you build a measurement system that catches regressions across all widget types and data sources (e.g., enforcing correct grouping, sorting, and time overrides), and is easy to use and extend by dozens of teams? If those are the problems you want to spend your time on, come build this with us. 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: Own the evaluation strategy for Dashboards, as well as sister teams within our organization. Define the metrics — offline and online, quality and cost, single-turn and multi-turn — that the team and the broader organization optimize against. Build the eval datasets, golden traces, and regression harnesses that catch quality changes before they hit customers, an

Team description At Datadog, AI agents are becoming first-class consumers of observability, security, and software delivery data — from third-party coding agents like Claude Code, Cursor, and Copilot, to our own Bits SRE, Bits Assistant, and Bits Dev Agent. The Agentic Interfaces team owns the platform that connects these agents to Datadog: the MCP Server, the tools and retrieval surfaces agents call into, and — critically — the evaluation systems that tell us whether an agent's experience on Datadog data is actually getting better over time. This role is about that last piece. We're hiring a Staff Applied Scientist to define what "good" means for an Agentic interface at Datadog and to build the measurement systems that make it true. "Good" isn't one number — it spans answer quality, tool-selection accuracy, retrieval relevance, latency, token cost, and end-to-end agent success on real customer workflows. You'll design the evals, build the datasets, define the metrics, and partner with the AI engineers on the team to land the platform that lets every product group at Datadog ship integrations that are demonstrably better release over release. The space is full of open research questions. How do you evaluate an agent end-to-end when the trajectory is non-deterministic? How do you score tool selection when the tool catalog has hundreds of entries and grows weekly? How do you build a measurement system that catches regressions across first-party and third-party agents at once, without each team writing their own harness? If those are the problems you want to spend your time on, come build this with us. Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply. What You’ll Do: Own the evaluation strategy for Datadog's AI agent integrations. Define the metrics — offline and online, quali

We're looking for an Engineering Manager II to own and grow the Observability Pipelines engineering org at a pivotal moment in the product's lifecycle. Observability Pipelines is Datadog's on-premise, vendor-agnostic telemetry pipeline product, with a lot still to build as it grows and scales. It sits at the center of a fast-consolidating market, is central to Datadog's data pipeline optimization story for Logs and Metrics customers. This is a build-and-scale opportunity: you'll grow the management and technical leadership layers, co-own the roadmap with Product, and define how this org operates as it continues to expand. At Datadog, we place value in our office culture - the relationships that it builds, the creativity it brings to the table, and the collaboration of being together. We operate as a hybrid workplace to ensure our employees can create a work-life harmony that best fits them. What You'll Do: Directly manage the OP org including EM1s across NYC and Paris, set technical direction, and be the connective tissue across a distributed team Build out the management and technical leadership layers as the org continues to grow - today ~20 ICs Partner directly with Product to co-own the roadmap and strategy, helping decide where OP’s engineering investment goes next Set and evolve the operating rhythm across the group: planning cadence, on-call and incident standards, and cross-team alignment Own key cross-org relationships with the SaaS Logs Pipelines team, the BYOC team, and the Vector open-source community Coach managers and senior engineers, and build the succession and growth plans that let the org scale beyond you Who You Are: Experienced managing managers across distributed teams, with a track record of raising the bar on how those teams operate, not just delivering through them Back

As a Mid-Market Sales Engineer, you will provide technical expertise through sales presentations, product demonstrations, and supporting technical evaluations (POVs). Sales Engineers help qualify and close opportunities with customers and partners and have a voice with the product team to help prioritize features based on input from customers, competitors, and partners. Additionally, you will work with various teams to resolve customer concerns, escalate bug issues, and serve as an ambassador for our brand. If you want to join a friendly, passionate team with limitless potential, we’d love to meet you! 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: Partner with the sales team to articulate the overall Datadog value proposition, vision and strategy to customers Continually learn new technology to build competitive knowledge, technical skill, and credibility Assist with technical discovery on key accounts and opportunities Deliver tailored product and technical presentations with potential clients Help clients evaluate the platform and assist when they run into roadblocks. Own technical engagement with customers during the trial phase. This entails communicating datadog’s value throughout an evaluation and working with customers on any identified issues or concerns to successful conclusion Proactively engage and communicate with customers and Datadog business/technical teams regarding product feedback and competitive landscape Who You Are: </p&

As a Mid-Market Sales Engineer, you will provide technical expertise through sales presentations, product demonstrations, and supporting technical evaluations (POVs). Sales Engineers help qualify and close opportunities with customers and partners and have a voice with the product team to help prioritize features based on input from customers, competitors, and partners. Additionally, you will work with various teams to resolve customer concerns, escalate bug issues, and serve as an ambassador for our brand. If you want to join a friendly, passionate team with limitless potential, we’d love to meet you! 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: Partner with the sales team to articulate the overall Datadog value proposition, vision and strategy to customers Continually learn new technology to build competitive knowledge, technical skill, and credibility Assist with technical discovery on key accounts and opportunities Deliver tailored product and technical presentations with potential clients Help clients evaluate the platform and assist when they run into roadblocks. Own technical engagement with customers during the trial phase. This entails communicating datadog’s value throughout an evaluation and working with customers on any identified issues or concerns to successful conclusion Proactively engage and communicate with customers and Datadog business/technical teams regarding product feedback and competitive landscape Who You Are: Someone with a minimum of 1.5 years experience in a Sales Engineering role Previous Observability experience Passionate about educating customers on observability risks that are meaningful to their business, and able to build and execute an evaluation plan with a customer Someone with strong written and oral communicati

G&A at Datadog rapidly scales the physical space, hiring, onboarding, and financial and legal systems to keep our business running in top form. As a Deal Desk Analyst, you will work cross-functionally with our Sales Operations, Billing, Contracts and Legal teams to provide quoting and deal structuring support to the Global Sales Team. This will be a growth position as Datadog’s business continues to expand. 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: Develop in-depth knowledge of Datadog’s licensing and pricing models to provide deal structuring and quoting support to our global sales teams Be a creative problem solver who finds a way to meet customers’ needs while adhering to Datadog’s selling policies Solve customer satisfaction issues following execution of the deal Actively negotiate deals directly with the customer as needed Work cross functionally across various stakeholder groups including legal, contracts, sales operations, order management, revenue, finance and product management Function as point of contact and subject matter expert for Sales on deal pricing matters Drive adherence to internal controls, protocols and business rules Who You Are: At least 4 years of overall experience including related processes such as sales operations, finance, sales strategy, and sales enablement At least 2 years of experience with deal structuring/quoting complex SaaS transactions for a fast-growing multi-national company Working knowledge of revenue recognition principles Must be comfortable representing the company to customers in negotiations and resolving customer satisfaction issues Strong attention to detail Ability to multi-task Strong communication skills Ability to work in fast paced, high press

Datadog is looking for a driven, entrepreneurial Customer Marketing Manager to join our Corporate Marketing team — a group of talented professionals responsible for sourcing, creating, and amplifying stories of customers who are achieving meaningful technology and business outcomes with Datadog. This role is designed for marketers who thrive in dynamic environments, are passionate about building genuine customer relationships, and know how to turn great stories into compelling, data-driven programs. 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: Source and track opportunities to promote customer wins by working with cross-functional partners across product marketing, partner marketing, sales, customer success, marketing operations, demand generation, and more Track and report on program performance, including participation rates, customer reception, content output, and influenced pipeline and closed deals Build a portfolio of customer advocates through online and in-person engagements to source strong stories and promotional opportunities Interview customers and product leaders — in-person and on camera — to produce customer marketing assets, like case studies, video testimonials, promotional quotes, and slides Design, deliver, and continuously optimize programs and incentive strategies that attract customers to participate in advocacy activities Lead programs that drive high-quality customer reviews to peer review sites such as Gartner Peer Insights, G2, and TrustRadius Influence how the broader team operates by modeling best practices, championing process improvements, and driving adoption of AI tools and cross-team efficiencies Who You Are: You have 4+ years of experience in customer marketing and/or advocacy for a B2B technology company

Datadog Sales Engineers help qualify and close opportunities with customers and partners. You will provide technical expertise through sales presentations, product demonstrations, and supporting technical evaluations (POCs). Sales Engineers have a voice with the product team to help prioritize features based on input from customers, competitors, and partners. Additionally, you will work with various teams to resolve customer concerns, escalate bug issues, and serve as an ambassador for our brand. If you want to join a friendly, passionate team with limitless potential, we’d love to meet you! 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: Partner with the sales team to articulate the overall Datadog value proposition, vision and strategy to customers Continually learn new technology to build competitive knowledge, technical skill, and credibility Deliver product and technical presentations with potential clients Have a direct line of communication with the product team to collaborate on feature requests Help clients onboard the product and assist when they run into roadblocks. Think creatively about a wide variety of technical challenges during the pre-sales life cycle Who You Are: Enjoys a hybrid office culture and spending time in-person at our Boston office Has at least one year of experience in a technical sales and/or post-sales role Has a working knowledge of modern web development, DevOps monitoring, and cloud architecture/technologies Enjoys collaborating and teaming with others Demonstrates strong written and oral communication skills Comfortable and confident in delivering technical presentations/demos Can multi-task, manage time well, and be responsive to others Curious, eager to learn, and persistent in solving problems Able to si

G&A at Datadog rapidly scales the physical space, hiring, onboarding, and financial and legal systems to keep our business running in top form. As a Deal Desk Analyst, you will work cross-functionally with our Sales Operations, Billing, Contracts and Legal teams to provide quoting and deal structuring support to the Global Sales Team. This will be a growth position as Datadog’s business continues to expand. 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: Develop in-depth knowledge of Datadog’s licensing and pricing models to provide deal structuring and quoting support to our global sales teams Be a creative problem solver who finds a way to meet customers’ needs while adhering to Datadog’s selling policies Solve customer satisfaction issues following execution of the deal Actively negotiate deals directly with the customer as needed Work cross functionally across various stakeholder groups including legal, contracts, sales operations, order management, revenue, finance and product management Function as point of contact and subject matter expert for Sales on deal pricing matters Drive adherence to internal controls, protocols and business rules Who You Are: At least 4 years of overall experience including related processes such as sales operations, finance, sales strategy, and sales enablement At least 2 years of experience with deal structuring/quoting complex SaaS transactions for a fast-growing multi-national company Working knowledge of revenue recognition principles Must be comfortable representing the company to customers in negotiations and resolving customer satisfaction issues Strong attention to detail Ability to multi-task Strong communication skills Ability to work in fast paced, high press