Founding Sales Leader, SF

Datadog

The Datadog for Startups (DDFS) program helps the next generation of fast-scaling companies adopt best-in-class observability and security from day one. We're looking for the technical engine of this program - someone who can sit across from a startup CTO, earn credibility in the first five minutes, and help them see how Datadog fits into their stack before they've even finished describing it. You'll be the first technical member on a lean, five-person team, owning the technical motion end-to-end: discovery calls, demos, startup enablement, forward-deployed engineering projects, and representing Datadog at founder events across San Francisco. This isn't a traditional SE seat - it's part solutions architect, part technical consultant, part startup evangelist, and it requires someone adaptable, proactive, and ready to take initiative without being told what to do next. 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: * Run discovery calls with startup CTOs and engineering leads to identify quick wins, validate technical needs, and position Datadog against alternatives like Grafana, New Relic, Sentry, and Clickhouse * Deliver tailored Datadog demos and help startups get instrumented quickly - removing friction, showcasing value, and ensuring smooth technical onboarding, particularly around AI/ML observability, infrastructure scaling, and security * Build automation to improve internal team workflows - EX: outreach, reporting, the application process, and website updates * Represent Datadog for Startups at accelerator demo days, hackathons, conferences, founder dinners, and workshops across San Francisco * Build relationships across SF's startup ecosystem - founders, VCs, accelerator partners, and technical communities - and develop thought leadership content for technical founder audiences Who You Are: * 5-7+ years in solutions architecture, pre-sales engineering, technical consulting, or a similar customer-facing technical role at a SaaS or cloud company, with broad fluency across cloud infrastructure, containers, Kubernetes, CI/CD, and modern application frameworks * A tinkerer with genuine, personal interest in AI and emerging technologies - you've used tools like Claude, ChatGPT, Codex, or Cursor outside of work and follow what's happening with agentic workflows, vibe coding, and codegen because you find it interesting * Consultative mindset - you do the overview first, then go deep. You identify customer needs and quick wins in a first conversation, not just recite product features * Strong presence and communication skills - you can command a room of technical founders, run a compelling demo, and hold your own in an unscripted conversation with a CTO * Adaptable and flexible - comfortable shifting between contexts, priorities, and audiences quickly, and thrive in ambiguity on a small, lean team * Based in San Francisco and actively engaged in the local tech/startup community, with startup experience (founded a company, early-stage engineer, or consulting/advisory to founders) strongly preferred 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. Benefits and Growth: * New hire stock equity (RSUs) and employee stock purchase plan (ESPP) * Continuous professional development, product training, and career pathing * Intradepartmental mentor and buddy program for in-house networking * An inclusive company culture, ability to join our Community Guilds (Datadog Affinity Slacks) * Access to Inclusion Talks with a focus on Diversity, Equity, and Inclusion * Free, global mental health benefits for employees and dependents age 6+ * Competitive global benefits Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog. Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan. The reasonably estimated yearly salary for this role at Datadog is: $192,000—$240,000 USD ---------------------------------------------------------------------------------------------------------------------------------- About Datadog:  Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center. ---------------------------------------------------------------------------------------------------------------------------------- Equal Opportunity at Datadog: Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference.  Datadog endeavors to make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications.  Privacy and AI Guidelines: Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.

Meticulous

WHAT WE DO We're building the last piece of the puzzle to help companies unlock AI code generation - the part that makes it actually safe to ship. AI is enabling engineers to write code faster than ever before. But software review and testing hasn't caught up. Engineering leaders are drowning in long review cycles and more bugs than ever. The bottleneck isn't writing code anymore - it's everything that comes after it. We spent 3 years building the foundational technology to crack this - hard to replicate, and several years ahead of anything else on the market. Since then, we've grown 5x year-on-year and now work with some of the most AI-driven engineering teams in the world: Notion, ElevenLabs, Dropbox, Discord, LaunchDarkly, Wiz, CoreWeave, Wealthsimple, and more. Companies like Dropbox, Wiz, and Notion often pay more for Meticulous than any other software product in their stack, and spontaneously refer us to others. We're backed by the same investors behind Twilio, Twitch, Intercom, and PagerDuty. Individual investors include the founders of Vercel, Datadog, Segment, and Dropbox, the CTO of GitHub, the CPO of Adobe, the head of Engineering at Cursor, and many more. Our mission is to radically accelerate the pace of software development by empowering every engineer to ship at the speed their agents write code. This is an opportunity to join a company in hypergrowth as we scale from millions of annual recurring revenue to $100M ARR. If this excites you, come help us build it! THE ROLE THE FIRST FORWARD DEPLOYED ENGINEER IN SAN FRANCISCO As Meticulous's first Forward Deployed Engineer in San Francisco, you'll establish our US FDE presence and help define how this function operates from the ground up. The FDE team is still small and the playbook is still being written - you'll be instrumental in shaping the processes, tooling, and best practices that the function runs on as it scales. You'll work directly with engineering leaders at the world's most AI-driven companies, understanding their unique architectures and crafting solutions that work for their specific needs. This role demands an unusual combination of deep technical expertise and entrepreneurial drive, you'll be writing high-performance code one day and presenting architectural decisions to VPs of Engineering the next. CORE RESPONSIBILITIES This role spans both customer work and engineering. You own each customer end-to-end - and do what’s needed to make sure Meticulous is transformational for them. This involves everything from changes to core product to owning the customer relationship: * Architect and deploy at scale: Work with a customer to understand their full architecture, design implementation strategies that fit their systems, and pair with their engineers to deliver them. * Evolve the core product to make the customer successful: This can range from debugging and fixing issues that are blocking the rollout (which often go deep into the core technology, such as the deterministic browser), to shipping features that will be transformative for the customer you’re focused on, but also move the product forward itself e.g. rework parts of Meticulous to work at a new level of scale required by the customer. * Own the technical relationship and lead the pilot: Be the technical lead to engineering leadership (VPs Eng, Staff+ engineers) at each customer - driving scoping, integration, and rollout. A founder or account executive handles pricing and contracts; the two of you operate as a pod per account. * Guide the direction of the product based on what you learn in the field: As you see how the product performs, and how engineers workflows are rapidly evolving, work out what do we need to build to unlock the next level of automating software development? Where there are improvements which make sense to own and ship, ship them; where the work is larger and needs deeper scoping pair with core engineering team to make them happen. * Build the playbook: The FDE function is still being defined. You'll be instrumental in establishing the processes, tooling, and best practices that make each deployment smoother and faster than the last, creating the leverage that lets the team scale. WHAT WE'RE LOOKING FOR * Exceptional engineering skills: Typically 3+ years in a demanding technical role, but we'll consider exceptional candidates with 1+ years of experience. * Highly agentic: you have a bias to action, move fast, take ownership without being asked, and get genuinely frustrated when things stall - this role demands entrepreneurial self-drive * Strong communication skills: You can explain complex technical concepts to both engineers and executives, and you're energized by customer collaboration * Willingness to travel: Approximately 25% travel to customer sites. Expect to spend your first ~2 months in London embedded with the core engineering team. THIS ROLE IS NOT FOR YOU IF… * You want a pure IC engineering role with no customer contact * You need structured handoffs, clear specs, and a defined process to follow * You expect regular hours and no travel - our team, customers, and investors span SF, London, and NYC * You want engineering work that's insulated from customers and their problems YOU MAY LOOK LIKE… * Senior IC at a top tech company ready to leave the bureaucracy behind and own real customer outcomes end-to-end * Ex-founder or technical founding engineer who wants to keep the founder-energy but plug into a company with product-market fit and a clear path to scale * Forward Deployed Engineer at OpenAI, Scale, or Anthropic looking for an earlier-stage version of the same work * Solutions architect or staff engineer who wants more deep engineering and less PowerPoint WHAT YOU'LL GAIN HELP BUILD A NEW FUNCTION As the first FDE in San Francisco and one of the earliest FDEs at Meticulous, you'll be instrumental in defining how this team operates, from processes and tooling to how it scales. Clear path into leadership as the function grows. EXCEPTIONAL GROWTH You grow through a combination of the people you work with, and the experiences you’re exposed to. Within that context: * Our philosophy is that density of talent is what matters; and so we’ve focused on keeping the team small but with exceptional individuals. You’ll get to collaborate with world-class engineers who previously led 100+ person organizations at top companies, and we expect you’ll find the team is beyond any you’ve worked in before, within big tech (Google, Meta, etc.) or otherwise. This, combined with a focus on learning and growing together, means we’re able to learn from each other at rapid pace. * Beyond growing your skills through engineering and collaboration, the role involves spending a lot of time with engineering leaders at the fastest growing tech companies and leading firms in the world. We’ve found this gives us a unique exposure to a huge range of technologies, practices, techniques, codebases, architectures, cultures, learnings - what works, what doesn’t. It’s a valuable bird eye view of collective learnings and experiences. These learnings normally take years or decades to build up as you move between companies. There are few startups that grow as fast as we do. You’ll be joining a small team on an exceptional trajectory. Through this comes unique growth, but also unique network. EXPAND YOUR NETWORK Our investor network is one of the most active in tech - we'll use it to connect you with whoever helps you do your job better. You’ll work with engineering leaders across many leading tech companies, often at the highest levels. Given the speed of growth, and desirability of the product amongst the leading enterprises, Meticulous provides the opportunity to build a network of connections across the full span of the technology world. SOLVE NOVEL PROBLEMS Work on challenges at the intersection of browser technology, testing infrastructure, and large-scale system design that few engineers ever encounter - to help build something that changes the way software is developed. WORLD-CLASS COMPENSATION Base salary $200K-$400K plus significant equity, exceeding compensation at top technology companies and startups. PERKS ♥️ * 🍲 Unlimited food & drinks in office - including daily lunch as a team, and your own Amazon business account to buy whatever snacks you want for the office. * 💻 A setup you’ll love - everyone has a standing desk, brand new Macbook, your choice of ergonomic peripherals, and a $2.5k WFH budget to make home just as good * 🌴 Team offsites - we work and play hard, we’ve done offsites in Italy, Abu Dhabi and local 5-star resorts * 📚 Unlimited book budget - we have a growing in-office library and actively encourage everyone to add to it, whether you want to ramp up your knowledge of software testing, or become a better startup operator! * + many more!   LIFE AT METICULOUS We believe autonomous testing will enable the automation of the majority of software development. You'll be at the forefront of this transformation, working with the companies that will be first to realize this future. This role is on-site because we've found that the speed of iteration and depth of collaboration required for both customer success and technical excellence happens best in person.

Notion

WHO WE ARE Notion is the collaborative AI workspace where teams and agents think together. We're building one place where your knowledge, projects, meetings, and AI tools live side by side, so work is faster, clearer, and less fragmented. Millions of individuals, small teams, and large companies run their work on Notion. Notinos (our employees) are customer zero in bringing this future of work to life. We care about craft, building things that last, and the belief that great work is still fundamentally human. Our goal isn’t to ship the next feature. Each and every team of Notinos is working to set the standard for how humans work together in the AI era. From building a business’s system of record to making and managing AI agents to automating away the busy work, we care deeply about giving our customers more time for their life’s work. ABOUT THE ROLE Notion is transitioning from ‘start-up’ to ‘scale-up’. The AMER region currently accounts for a significant portion of our user base and global revenue. We are looking for an exceptional Sales leader to help scale us to the next level. Given the strong subscription and usage based revenue model, building out our sales program is a vital part of our long term growth strategy. This leader will hire, inspire, and coach a group of founding AEs to sell transformational software that drives real change within the world's largest companies. The ideal candidate blends strong operational discipline with a consultative, value-based selling approach—helping customers reimagine how their organizations collaborate, align, and execute. They excel in ambiguity, can scale proven playbooks while remaining hands-on, and are passionate about building a winning culture from the ground up. The AMER sales team drives both new customer acquisition and revenue expansion from existing customers. The team is responsible for generating opportunities through strategic outbound prospecting, while helping self-service customers upgrade to Enterprise products. WHAT YOU'LL ACHIEVE * As an Enterprise Sales Leader, you will work directly with the Head of Enterprise Sales, AMER to create and execute strategies for developing new revenue in this segment. * You will recruit, develop and lead a team of Account Executives, managing daily operations, setting clear performance expectations, and fostering a culture of high achievement and an environment where AE’s can do the best work of their career. * Partner with cross-functional leaders within Sales Strategy, Marketing and Sales Development teams to plan territory mapping and pipeline development programs. * Partner with the Customer Success and Solutions Engineering teams to onboard new customers and refine our customer journey to set new customers up for longer term success with Notion. * You understand the importance of communication and collaboration in defining a customer-first mentality, and you will work closely with our Product, Marketing and Commercial leadership teams to drive insight in to Ideal Customer Profile. * Help build the foundations of Sales at Notion: As an early member of our sales org, you'll be instrumental in helping define our sales assisted motions. * Join a fantastic team at a pivotal time: We've achieved profitability and grown to over 100 million users, creating vast opportunities ahead. This is the perfect moment to join and help shape our future expansion. * Meaningfully shape our future product: As you engage with customers, you'll gain insights to help us serve them better — and work with product to inform what we do next. * Elevate your skills as we tackle our most impactful challenges: We've achieved more than teams 10x our size in less time — and there's so much more to do and learn. SKILLS YOU'LL NEED TO BRING * You have 3+ years experience as a direct sales leader/manager within Enterprise/Strategic Accounts * Strong track record of achieving sales targets across teams and individually * Skilled in managing and coaching through the full sales cycle from prospecting to closing * You have strong recognized leadership skills with a focus on empowerment, positive-mindsets, collaboration and ability to inspire a team of direct reports * You are comfortable with the ambiguity and pace of iteration of an early-stage startup * You have a growth mindset and thrive in the building stage of a nascent team * You view setbacks as learning opportunities, not failures * You have a high EQ and exceptional interpersonal skills, ability to manage influence through persuasion, negotiation, and consensus building * You have an analytical mindset and enjoy problem solving as part of a regional leadership team * You have strong empathy for customers and passion for revenue and growth * You have a good understanding of value drivers in recurring revenue business models * You don’t need to be an AI expert, but you’re curious and willing to adopt AI tools to work smarter and deliver better results. NICE TO HAVES * You've built new business and expansion sales playbooks or processes * You've been a first or early hire at a fast growing start up before * Experience using Salesforce for accurate forecasting * Experienced in hiring and training talent at scale * Ability to function in a “Player/Coach” capacity as we scale AMER * Strong perspective and experience in building sales strategies for product-led growth (PLG) companies Notion is committed to providing highly competitive cash compensation, equity, and benefits. The compensation offered for this role will be based on multiple factors such as location, the role’s scope and complexity, and the candidate’s experience and expertise, and may vary from the range provided below. For roles based in San Francisco or New York City, the estimated range for total on target earnings (including base salary and on target incentive pay) for this role is $350,000 - 400,000 per year. By clicking “Submit Application”, I understand and agree that Notion and its affiliates and subsidiaries will collect and process my information in accordance with Notion’s Global Recruiting Privacy Policy and NYLL 144. #LI-Onsite A NOTE ON AI You don’t need deep AI expertise for every role, but we do expect every Notino to be intellectually curious, drawn to tinkering and discovery, and excited to use AI as a real collaborator in their work. For some roles, AI fluency is a core requirement — when that’s the case, we'll say so explicitly in the qualifications. People who thrive here don’t treat AI as a novelty. They use it to think better, and make their work easier for others to build on. EQUAL OPPORTUNITY & ACCOMMODATIONS We hire talented people from a wide range of backgrounds. If you’re excited about this role but don’t meet every bullet, we still encourage you to apply. Notion is an equal opportunity employer and does not discriminate on the basis of any legally protected characteristic. Consistent with applicable law, we will consider for employment qualified applicants with arrest and conviction records. Notion provides reasonable accommodations during the application process; if you need one, please let your recruiter know. Notion is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Notion considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Notion is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, please let your recruiter know.