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Work at a Startup Startup Jobs Resume Review Education How it Works Log In Sales Development Representative at Raindrop(W24) $70K - $110K • 0.05% - 0.15% Sentry for AI Agents San Francisco, CA, US Full-time US citizen/visa only 1+ years Apply now About Raindrop Monitor your AI app the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI products. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast. About the role About the Role Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100 companies and leading AI companies including Vercel, Speak, and Clay use Raindrop to detect silent failures in production. We're hiring a Sales Development Representative to build our outbound pipeline engine from the ground up. You'll prospect into engineering teams: AI engineers, engineering leaders, CTOs, and technical founders. Developers ignore generic outreach, so this role is about research, relevance, and writing, not dialing through call lists. You'll find the companies shipping AI agents, figure out where their systems are failing, and start conversations that engineers actually want to have. This is not a traditional SDR role. You'll work directly with Raindrop's Head of GTM and founders to shape our outbound motion, and you'll be first in line for an AE path as the team grows. Why It Matters AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. AI agents often fail silently, leaving engineering teams with little visibility into how their systems are actually performing. The current status quo is manually reviewing millions of logs and debugging evals that don't match real-world behavior. Evals are like unit tests: they confirm that a model handled specific test cases correctly. But production agents call thousands of tools, run for hours, and encounter millions of unpredictable actions. Raindrop learns the unique shape of each AI agent's issues. Engineering teams can track failures and behaviors across 100% of their production data, understand how frequently they occur, see which users are affected, and investigate the underlying conversations and traces. As an early member of the GTM team, you'll play a fundamental role in bringing this new category of software to market. Our Investors We're backed by Lightspeed and leading AI companies and founders, including Figma Ventures, Vercel Ventures, Amjad Masad and Michele Catasta of Replit, Walden Yan of Cognition, Koen Bok and Jorn van Dijk of Framer, Andrew Hsu of Speak, Akshay Kothari of Notion, and more. Your Focus Build and own outbound pipeline: research accounts, identify the right people, and book qualified meetings for our AE team Build AI-powered outbound systems that personalize at scale. High volume, but every email reads like it was researched by hand Run signal-based prospecting (GitHub activity, product launches, incident postmortems, hiring patterns, AI agent releases) instead of spray-and-pray sequences Qualify inbound leads and route them fast Track what's working: reply rates, meeting rates, channel performance, and messaging experiments Turn patterns from prospect conversations into ICP, positioning, and messaging insights Help define the outbound playbook the future SDR team will run Ideal Candidate Proven ability to generate cold pipeline: meetings booked from accounts with no prior relationship, in markets where your network doesn't help Exceptional written communication; your emails and DMs are the first impression of Raindrop Builds with AI, not just uses it: agents, enrichment pipelines, Clay-style workflows that make one person prospect like a team of five Technically curious: genuinely wants to understand how AI agents work, what a trace is, and why silent failures matter Experience prospecting into engineers, technical leaders, or developer audiences, or the instincts to know why devs hate typical sales outreach Resilient, self-motivated, and consistent. Outbound is a volume game played with precision Coachable, with examples of feedback that changed your numbers Highly organized: pipeline hygiene, follow-ups, and CRM discipline without being told Ambitious: wants to earn a path to AE and help build the GTM team Interested in AI products and developer tools, ideally through hands-on personal use Must be in person in San Francisco or willing to relocate Strong candidates may come from developer tools, observability, infrastructure, cloud, data, security, APIs, or AI/ML tooling. We're also open to career-changers with technical backgrounds who want to break into sales. You'll Thrive Here If Engineers reply to your cold emails asking to learn more, not to unsubscribe You use AI to send 200 emails that each read like you sent 10 You treat outbound like a product: experiment, measure, iterate You want direct ownership, fast feedback, and a real path to closing deals You get energy from starting conversations no one asked for Compensation $70-80K base, $100-110K OTE with uncapped commission, plus equity Apply now Other jobs at Raindrop Account Executive San Francisco, CA, US Full-Time $120K - $140K 0.08% - 0.22% 6+ Years View job Forward Deployed Engineer (FDE) San Francisco, CA, US Full-Time $130K - $200K 3+ Years View job Founding Recruiter San Francisco, CA, US Full-Time $150K - $200K 0.10% - 0.50% 3+ Years View job Security Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 6+ Years View job Developer Experience Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 3+ Years View job Hundreds of YC startups are hiring on Work at a Startup. 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Listed by Raindrop for a position based in the United States. Employers on this board attest they are hiring domestically.

Sales

36 days ago

Account Executive

Raindrop · San Francisco, CA, US

Pay

$120k–140k

Setting

On-site

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Work at a Startup Startup Jobs Resume Review Education How it Works Log In Account Executive at Raindrop(W24) $120K - $140K • 0.08% - 0.22% Sentry for AI Agents San Francisco, CA, US Full-time US citizen/visa only 6+ years Apply now About Raindrop Monitor your AI app the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI products. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast. About the role About the Role Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100 companies and leading AI companies including Vercel, Speak, and Clay use Raindrop to detect silent failures in production. We’re hiring an Account Executive to help build our sales motion from the ground up. You’ll sell a deeply technical product to engineering teams, working directly with AI engineers, engineering leaders, CTOs, and founders. You’ll own the full sales cycle, from identifying accounts and running discovery through technical evaluation, security, procurement, and close. You do not need to be an engineer. You do need to be technically curious, ask sharp questions, understand ambiguous systems and workflows, and build genuine trust with engineers. This is not a traditional SaaS sales role. You’ll work closely with Raindrop’s founders, engineers, and customers to shape how we sell, whom we sell to, and what we build. Why It Matters AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. AI agents often fail silently, leaving engineering teams with little visibility into how their systems are actually performing. The current status quo is manually reviewing millions of logs and debugging evals that don’t match real-world behavior. Evals are like unit tests: they confirm that a model handled specific test cases correctly. But production agents call thousands of tools, run for hours, and encounter millions of unpredictable actions. Raindrop learns the unique shape of each AI agent’s issues. Engineering teams can track failures and behaviors across 100% of their production data, understand how frequently they occur, see which users are affected, and investigate the underlying conversations and traces. As an early member of the GTM team, you’ll play a fundamental role in bringing this new category of software to market. Our Investors We’re backed by Lightspeed and leading AI companies and founders, including Figma Ventures, Vercel Ventures, Amjad Masad and Michele Catasta of Replit, Walden Yan of Cognition, Koen Bok and Jorn van Dijk of Framer, Andrew Hsu of Speak, Akshay Kothari of Notion, and more. Your Focus Own the full sales cycle, from outbound and discovery through evaluation, procurement, negotiation, and close Build relationships with AI engineers, engineering leaders, CTOs, and technical founders Run sharp discovery that uncovers both technical pain and business urgency Understand customers’ AI systems, production workflows, evaluation processes, and monitoring challenges Partner closely with engineering during technical evaluations and pilots Navigate security, legal, and procurement without losing momentum Build repeatable outbound, discovery, qualification, and closing processes Turn patterns from customer conversations into product, positioning, and go-to-market insights Help define our ideal customer profile, sales motion, and future GTM team Ideal Candidate Proven ability to close technical B2B software deals Experience selling to engineers, technical leaders, or other highly technical buyers Strong discovery skills and a genuine interest in understanding how customers’ systems work Able to translate technical pain into clear business impact Curious, low-ego, and comfortable admitting what you don’t know Fast learner who can become credible on APIs, infrastructure, AI systems, and developer workflows More interested in solving the customer’s problem than running a rigid sales playbook Comfortable operating quickly with ambiguity and incomplete information Willing to prospect, build process, unblock deals, and do whatever else the role requires Interested in AI products and developer tools, ideally through prior work or hands-on personal use Excited to work directly with company leadership and own high-impact work from day one Must be in person in San Francisco or willing to relocate Strong candidates may come from developer tools, observability, infrastructure, cloud, data, security, APIs, or AI/ML tooling. We’re also open to technical founding AEs and sales engineers who have moved into closing roles. You’ll Thrive Here If Engineers leave your calls feeling understood, not sold to You ask questions before pitching You can move between technical details and executive-level business outcomes You enjoy figuring out a sales process rather than inheriting one You want direct ownership, fast feedback, and a meaningful role in shaping the company Apply now Other jobs at Raindrop Sales Development Representative San Francisco, CA, US Full-Time $70K - $110K 0.05% - 0.15% 1+ Years View job Forward Deployed Engineer (FDE) San Francisco, CA, US Full-Time $130K - $200K 3+ Years View job Founding Recruiter San Francisco, CA, US Full-Time $150K - $200K 0.10% - 0.50% 3+ Years View job Security Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 6+ Years View job Developer Experience Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 3+ Years View job Hundreds of YC startups are hiring on Work at a Startup. Sign up to see more › Work at a Startup Jobs Internships Events How it works Sign in Y Combinator About YC Press Privacy & Terms Contact Jobs by Role Software Engineer Jobs Design & UI/UX Jobs Product Manager Jobs Sales Jobs Marketing Jobs Support Jobs Operations Jobs Jobs by Location Software Engineer Jobs in San Francisco Product Manager Jobs in San Francisco Software Engineer Jobs in New York Product Manager Jobs in New York Software Engineer Jobs in Los Angeles Product Manager Jobs in Los Angeles Remote Jobs Remote Software Engineer Jobs Remote Design & UI/UX Jobs Remote Product Manager Jobs Remote Sales Jobs Remote Marketing Jobs Remote Support Jobs Remote Operations Jobs

Listed by Raindrop for a position based in the United States. Employers on this board attest they are hiring domestically.

Engineering

71 days ago

Forward Deployed Engineer (FDE)

Raindrop · San Francisco, CA, US

Pay

$130k–200k

Setting

On-site

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Work at a Startup Startup Jobs Resume Review Education How it Works Log In Forward Deployed Engineer (FDE) at Raindrop(W24) $130K - $200K Sentry for AI Agents San Francisco, CA, US Full-time US citizen/visa only 3+ years Apply now About Raindrop Monitor your AI app the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI products. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast. About the role About the role Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100 and fastest AI companies including Vercel, Speak, Clay, use Raindrop to get alerts about silent failures with their AI agents. Raindrop sends alerts when AI agents misbehave, so AI engineers can dig into the conversations or traces, understand the root cause, and fix it, fast. Why It Matters AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. But AI agents fail silently, leaving engineers with almost no visibility into how their agents are actually performing. The current status quo is sifting through millions of logs and trying debug flaky evals that just aren't matching real world results. Evals are like unit tests, they confirm your model got specific test cases right. But in the real world agents call thousands of tools, run for hours, and encounter millions of unpredictable actions. That’s where Raindrop comes in. It learns the unique shape of each AI agent’s issues. Starting from presets like Laziness, Forgetting, or Task Failure, to automatically tuning itself to each agent and discovering unknown unknowns. With one click of a button, AI engineers start tracking issues or topics across 100% of their production data. They can see frequency over time, how many users are affected, relevant properties and more. In order to process hundreds of millions of events, we gradually train small, custom models, private to each company, that learn to uniquely understand how their product is used. As part of the early team, you’ll play a fundamental role in shaping the company - from making strategy and product decisions, to helping scale the team, to shaping the future of AI agents. Our Investors We’re backed by incredible investors including Lightspeed and leading AI companies including Figma Ventures, Vercel Ventures, founders of Replit (Amjad Masad and Michele Castata), Cognition (Walden Yan), Framer (Koen Bok and Jorn van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more. Your Focus Embed with our customers to get them up and running on Raindrop Own customer problems end-to-end, debugging across their agents and our platform Turn what you learn on the ground into product feedback that shapes our roadmap Ideal Candidate Top 0.1% communicator who would rather be in front of customers than heads-down all day Strong engineer who can read a codebase, debug production systems, and fix customer bugs hands-on Interest in AI products + tools (ideally experience building these or an avid user) Growth mindset Willing to do whatever it takes to solve a problem Excited to work closely with leadership and own high-impact work from day one. Must be in person in San Francisco (or willing to move) Apply now Other jobs at Raindrop Sales Development Representative San Francisco, CA, US Full-Time $70K - $110K 0.05% - 0.15% 1+ Years View job Account Executive San Francisco, CA, US Full-Time $120K - $140K 0.08% - 0.22% 6+ Years View job Founding Recruiter San Francisco, CA, US Full-Time $150K - $200K 0.10% - 0.50% 3+ Years View job Security Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 6+ Years View job Developer Experience Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 3+ Years View job Hundreds of YC startups are hiring on Work at a Startup. Sign up to see more › Work at a Startup Jobs Internships Events How it works Sign in Y Combinator About YC Press Privacy & Terms Contact Jobs by Role Software Engineer Jobs Design & UI/UX Jobs Product Manager Jobs Sales Jobs Marketing Jobs Support Jobs Operations Jobs Jobs by Location Software Engineer Jobs in San Francisco Product Manager Jobs in San Francisco Software Engineer Jobs in New York Product Manager Jobs in New York Software Engineer Jobs in Los Angeles Product Manager Jobs in Los Angeles Remote Jobs Remote Software Engineer Jobs Remote Design & UI/UX Jobs Remote Product Manager Jobs Remote Sales Jobs Remote Marketing Jobs Remote Support Jobs Remote Operations Jobs

Listed by Raindrop for a position based in the United States. Employers on this board attest they are hiring domestically.

Human Resources

160 days ago

Founding Recruiter

Raindrop · San Francisco, CA, US

Pay

$150k–200k

Setting

On-site

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Work at a Startup Startup Jobs Resume Review Education How it Works Log In Founding Recruiter at Raindrop(W24) $150K - $200K • 0.10% - 0.50% Sentry for AI Agents San Francisco, CA, US Full-time US citizen/visa only 3+ years Apply now About Raindrop Monitor your AI app the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI products. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast. About the role Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100s and the fastest-growing AI companies (Vercel, Speak, Clay) use it to catch silent failures in production. When an agent misbehaves, Raindrop alerts the team, links to the trace, and surfaces the root cause so they can fix it fast. With Raindrop 2.0 (Self-Healing Agents), the loop closes itself: your coding agent fixes it, and the fix becomes an eval to prevent regressions. Why It Matters AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. But AI agents fail silently, leaving engineers with almost no visibility into how their agents are actually performing. The current status quo is sifting through millions of logs and trying debug flaky evals that just aren't matching real world results. Evals are like unit tests, they confirm your model got specific test cases right. But in the real world agents call thousands of tools, run for hours, and encounter millions of unpredictable actions. That’s where Raindrop comes in. It learns the unique shape of each AI agent’s issues. Starting from presets like Laziness, Forgetting, or Task Failure, to automatically tuning itself to each agent and discovering unknown unknowns. With one click of a button, AI engineers start tracking issues or topics across 100% of their production data. They can see frequency over time, how many users are affected, relevant properties and more. In order to process hundreds of millions of events, we gradually train small, custom models, private to each company, that learn to uniquely understand how their product is used. As part of the early team, you’ll play a fundamental role in shaping the company - from making strategy and product decisions, to helping scale the team, to shaping the future of AI agents. Our Investors We’re backed by incredible investors including Lightspeed and leading AI companies including Figma Ventures, Vercel Ventures, founders of Replit (Amjad Masad and Michele Castata), Cognition (Walden Yan), Framer (Koen Bok and Jorn van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more. Your Focus Own the end-to-end recruiting function: sourcing, outreach, interviewing, coordination, closing. Build a world-class top-of-funnel engine through relentless outbound sourcing, referrals, content, and other creative recruiting tactics Help make the company a magnet for top talent by building a reputation for talent density Track and analyze recruiting metrics (pipeline, offer acceptance rates, time-to-hire) to inform hiring strategies Ideal Candiate Has recruited strong engineering teams, ideally at high-growth startups or AI / dev tool companies. Proven ability to source, engage, and close standout engineering candidates in competitive markets. Understands technical talent deeply and has strong instincts for evaluating engineering profiles. Strong communication skills. Aggressive user of AI tools and automation; always looking for ways to make work more efficient and scalable. Growth mindset Highly organized and reliable. Willing to do whatever it takes to solve a problem. Excited to work closely with leadership and own high-impact work from day one. Must be in person in San Francisco (or willing to move) Apply now Other jobs at Raindrop Sales Development Representative San Francisco, CA, US Full-Time $70K - $110K 0.05% - 0.15% 1+ Years View job Account Executive San Francisco, CA, US Full-Time $120K - $140K 0.08% - 0.22% 6+ Years View job Forward Deployed Engineer (FDE) San Francisco, CA, US Full-Time $130K - $200K 3+ Years View job Security Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 6+ Years View job Developer Experience Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 3+ Years View job Hundreds of YC startups are hiring on Work at a Startup. Sign up to see more › Work at a Startup Jobs Internships Events How it works Sign in Y Combinator About YC Press Privacy & Terms Contact Jobs by Role Software Engineer Jobs Design & UI/UX Jobs Product Manager Jobs Sales Jobs Marketing Jobs Support Jobs Operations Jobs Jobs by Location Software Engineer Jobs in San Francisco Product Manager Jobs in San Francisco Software Engineer Jobs in New York Product Manager Jobs in New York Software Engineer Jobs in Los Angeles Product Manager Jobs in Los Angeles Remote Jobs Remote Software Engineer Jobs Remote Design & UI/UX Jobs Remote Product Manager Jobs Remote Sales Jobs Remote Marketing Jobs Remote Support Jobs Remote Operations Jobs

Listed by Raindrop for a position based in the United States. Employers on this board attest they are hiring domestically.

Engineering

188 days ago

Security Engineer

Raindrop · San Francisco, CA, US

Pay

$150k–250k

Setting

On-site

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Work at a Startup Startup Jobs Resume Review Education How it Works Log In Security Engineer at Raindrop(W24) $150K - $250K • 0.10% - 1.50% Sentry for AI Agents San Francisco, CA, US Full-time US citizen/visa only 6+ years Information Security Software Security Apply now About Raindrop Monitor your AI app the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI products. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast. About the role Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100s and the fastest-growing AI companies (Vercel, Speak, Clay) use it to catch silent failures in production. When an agent misbehaves, Raindrop alerts the team, links to the trace, and surfaces the root cause so they can fix it fast. With Raindrop 2.0 (Self-Healing Agents), the loop closes itself: your coding agent fixes it, and the fix becomes an eval to prevent regressions. Why It Matters AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. But AI agents fail silently, leaving engineers with almost no visibility into how their agents are actually performing. The current status quo is sifting through millions of logs and trying debug flaky evals that just aren't matching real world results. Evals are like unit tests, they confirm your model got specific test cases right. But in the real world agents call thousands of tools, run for hours, and encounter millions of unpredictable actions. That’s where Raindrop comes in. It learns the unique shape of each AI agent’s issues. Starting from presets like Laziness, Forgetting, or Task Failure, to automatically tuning itself to each agent and discovering unknown unknowns. With one click of a button, AI engineers start tracking issues or topics across 100% of their production data. They can see frequency over time, how many users are affected, relevant properties and more. In order to process hundreds of millions of events, we gradually train small, custom models, private to each company, that learn to uniquely understand how their product is used. As part of the early team, you’ll play a fundamental role in shaping the company - from making strategy and product decisions, to helping scale the team, to shaping the future of AI agents. Our Investors We’re backed by incredible investors including Lightspeed and leading AI companies including Figma Ventures, Vercel Ventures, founders of Replit (Amjad Masad and Michele Castata), Cognition (Walden Yan), Framer (Koen Bok and Jorn van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more. Your Focus Secure the platform end-to-end from application code to cloud infrastructure Design and implement security controls that scale with millions of requests per day Conduct threat modeling, security audits, and incident response Communicate directly with our customer’s security teams Ideal Candidate Has experience with security engineering at a fast-growing startup Familiar with compliance (SOC 2, HIPAA etc.) Has contributed to the security community (eg. exploits, open-source) Interest in AI products + tools (ideally experience building these or an avid user) Growth mindset Willing to do whatever it takes to solve a problem Strong communicator who can explain ideas clearly Must be in person in San Francisco (or willing to move) Apply now Other jobs at Raindrop Sales Development Representative San Francisco, CA, US Full-Time $70K - $110K 0.05% - 0.15% 1+ Years View job Account Executive San Francisco, CA, US Full-Time $120K - $140K 0.08% - 0.22% 6+ Years View job Forward Deployed Engineer (FDE) San Francisco, CA, US Full-Time $130K - $200K 3+ Years View job Founding Recruiter San Francisco, CA, US Full-Time $150K - $200K 0.10% - 0.50% 3+ Years View job Developer Experience Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 3+ Years View job Hundreds of YC startups are hiring on Work at a Startup. Sign up to see more › Work at a Startup Jobs Internships Events How it works Sign in Y Combinator About YC Press Privacy & Terms Contact Jobs by Role Software Engineer Jobs Design & UI/UX Jobs Product Manager Jobs Sales Jobs Marketing Jobs Support Jobs Operations Jobs Jobs by Location Software Engineer Jobs in San Francisco Product Manager Jobs in San Francisco Software Engineer Jobs in New York Product Manager Jobs in New York Software Engineer Jobs in Los Angeles Product Manager Jobs in Los Angeles Remote Jobs Remote Software Engineer Jobs Remote Design & UI/UX Jobs Remote Product Manager Jobs Remote Sales Jobs Remote Marketing Jobs Remote Support Jobs Remote Operations Jobs

Listed by Raindrop for a position based in the United States. Employers on this board attest they are hiring domestically.

Engineering

216 days ago

ML Engineer

Raindrop · San Francisco, CA, US

Pay

$150k–250k

Setting

On-site

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Work at a Startup Startup Jobs Resume Review Education How it Works Log In ML Engineer at Raindrop(W24) $150K - $250K • 0.10% - 1.50% Sentry for AI Agents San Francisco, CA, US Full-time US citizen/visa only 3+ years Python TypeScript Torch/PyTorch Apply now About Raindrop Monitor your AI app the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI products. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast. About the role Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100s and the fastest-growing AI companies (Vercel, Speak, Clay) use it to catch silent failures in production. When an agent misbehaves, Raindrop alerts the team, links to the trace, and surfaces the root cause so they can fix it fast. With Raindrop 2.0 (Self-Healing Agents), the loop closes itself: your coding agent fixes it, and the fix becomes an eval to prevent regressions. Why It Matters AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. But AI agents fail silently, leaving engineers with almost no visibility into how their agents are actually performing. The current status quo is sifting through millions of logs and trying debug flaky evals that just aren't matching real world results. Evals are like unit tests, they confirm your model got specific test cases right. But in the real world agents call thousands of tools, run for hours, and encounter millions of unpredictable actions. That’s where Raindrop comes in. It learns the unique shape of each AI agent’s issues. Starting from presets like Laziness, Forgetting, or Task Failure, to automatically tuning itself to each agent and discovering unknown unknowns. With one click of a button, AI engineers start tracking issues or topics across 100% of their production data. They can see frequency over time, how many users are affected, relevant properties and more. In order to process hundreds of millions of events, we gradually train small, custom models, private to each company, that learn to uniquely understand how their product is used. As part of the early team, you’ll play a fundamental role in shaping the company - from making strategy and product decisions, to helping scale the team, to shaping the future of AI agents. Our Investors We’re backed by incredible investors including Lightspeed and leading AI companies including Figma Ventures, Vercel Ventures, founders of Replit (Amjad Masad and Michele Castata), Cognition (Walden Yan), Framer (Koen Bok and Jorn van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more. Your Focus Build out a world-class product - servicing millions of requests a day + growing. Architect, implement, and scale ML pipelines Quick iteration without compromising on quality Deeply understand the customer Ideal Candidate Knows how to balance short-term and long-term speed Proven experience scaling applications Interest in AI products + tools (ideally experience building these or an avid user) Growth mindset Cares about building well-designed products Willing to do whatever it takes to solve a problem Must be in person in San Francisco (or willing to move) Apply now Other jobs at Raindrop Sales Development Representative San Francisco, CA, US Full-Time $70K - $110K 0.05% - 0.15% 1+ Years View job Account Executive San Francisco, CA, US Full-Time $120K - $140K 0.08% - 0.22% 6+ Years View job Forward Deployed Engineer (FDE) San Francisco, CA, US Full-Time $130K - $200K 3+ Years View job Founding Recruiter San Francisco, CA, US Full-Time $150K - $200K 0.10% - 0.50% 3+ Years View job Security Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 6+ Years View job Hundreds of YC startups are hiring on Work at a Startup. Sign up to see more › Work at a Startup Jobs Internships Events How it works Sign in Y Combinator About YC Press Privacy & Terms Contact Jobs by Role Software Engineer Jobs Design & UI/UX Jobs Product Manager Jobs Sales Jobs Marketing Jobs Support Jobs Operations Jobs Jobs by Location Software Engineer Jobs in San Francisco Product Manager Jobs in San Francisco Software Engineer Jobs in New York Product Manager Jobs in New York Software Engineer Jobs in Los Angeles Product Manager Jobs in Los Angeles Remote Jobs Remote Software Engineer Jobs Remote Design & UI/UX Jobs Remote Product Manager Jobs Remote Sales Jobs Remote Marketing Jobs Remote Support Jobs Remote Operations Jobs

Listed by Raindrop for a position based in the United States. Employers on this board attest they are hiring domestically.

Engineering

216 days ago

Developer Experience Engineer

Raindrop · San Francisco, CA, US

Pay

$150k–250k

Setting

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Work at a Startup Startup Jobs Resume Review Education How it Works Log In Developer Experience Engineer at Raindrop(W24) $150K - $250K • 0.10% - 1.50% Sentry for AI Agents San Francisco, CA, US Full-time US citizen/visa only 3+ years Apply now About Raindrop Monitor your AI app the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI products. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast. About the role Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100s and the fastest-growing AI companies (Vercel, Speak, Clay) use it to catch silent failures in production. When an agent misbehaves, Raindrop alerts the team, links to the trace, and surfaces the root cause so they can fix it fast. With Raindrop 2.0 (Self-Healing Agents), the loop closes itself: your coding agent fixes it, and the fix becomes an eval to prevent regressions. Why It Matters AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. But AI agents fail silently, leaving engineers with almost no visibility into how their agents are actually performing. The current status quo is sifting through millions of logs and trying debug flaky evals that just aren't matching real world results. Evals are like unit tests, they confirm your model got specific test cases right. But in the real world agents call thousands of tools, run for hours, and encounter millions of unpredictable actions. That’s where Raindrop comes in. It learns the unique shape of each AI agent’s issues. Starting from presets like Laziness, Forgetting, or Task Failure, to automatically tuning itself to each agent and discovering unknown unknowns. With one click of a button, AI engineers start tracking issues or topics across 100% of their production data. They can see frequency over time, how many users are affected, relevant properties and more. In order to process hundreds of millions of events, we gradually train small, custom models, private to each company, that learn to uniquely understand how their product is used. As part of the early team, you’ll play a fundamental role in shaping the company - from making strategy and product decisions, to helping scale the team, to shaping the future of AI agents.Our Investors We’re backed by incredible investors including Lightspeed and leading AI companies including Figma Ventures, Vercel Ventures, founders of Replit (Amjad Masad and Michele Castata), Cognition (Walden Yan), Framer (Koen Bok and Jorn van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more. Your Focus Ensure customers have a world-class developer experience integrating and using Raindrop Maintain, improve and add SDKs Help customers debug integration Write clear documentation, tutorials, and guides Quick iteration without compromising on quality Deeply understand the customer Ideal Candiate Knows how to balance short-term and long-term speed Strong programming, problem solving, and debugging skills Passion for working with developers and building developer communities Excellent technical writing skills Interest in AI products + tools (ideally experience building these or an avid user) Growth mindset Cares about building well-designed products Willing to do whatever it takes to solve a problem Must be in person in San Francisco (or willing to move) Apply now Other jobs at Raindrop Sales Development Representative San Francisco, CA, US Full-Time $70K - $110K 0.05% - 0.15% 1+ Years View job Account Executive San Francisco, CA, US Full-Time $120K - $140K 0.08% - 0.22% 6+ Years View job Forward Deployed Engineer (FDE) San Francisco, CA, US Full-Time $130K - $200K 3+ Years View job Founding Recruiter San Francisco, CA, US Full-Time $150K - $200K 0.10% - 0.50% 3+ Years View job Security Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 6+ Years View job Hundreds of YC startups are hiring on Work at a Startup. Sign up to see more › Work at a Startup Jobs Internships Events How it works Sign in Y Combinator About YC Press Privacy & Terms Contact Jobs by Role Software Engineer Jobs Design & UI/UX Jobs Product Manager Jobs Sales Jobs Marketing Jobs Support Jobs Operations Jobs Jobs by Location Software Engineer Jobs in San Francisco Product Manager Jobs in San Francisco Software Engineer Jobs in New York Product Manager Jobs in New York Software Engineer Jobs in Los Angeles Product Manager Jobs in Los Angeles Remote Jobs Remote Software Engineer Jobs Remote Design & UI/UX Jobs Remote Product Manager Jobs Remote Sales Jobs Remote Marketing Jobs Remote Support Jobs Remote Operations Jobs

Listed by Raindrop for a position based in the United States. Employers on this board attest they are hiring domestically.

Engineering

216 days ago

Backend Engineer

Raindrop · San Francisco, CA, US

Pay

$150k–250k

Setting

On-site

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Work at a Startup Startup Jobs Resume Review Education How it Works Log In Backend Engineer at Raindrop(W24) $150K - $250K • 0.10% - 1.50% Sentry for AI Agents San Francisco, CA, US Full-time US citizen/visa only 3+ years Python TypeScript Apply now About Raindrop Monitor your AI app the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI products. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast. About the role Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100s and the fastest-growing AI companies (Vercel, Speak, Clay) use it to catch silent failures in production. When an agent misbehaves, Raindrop alerts the team, links to the trace, and surfaces the root cause so they can fix it fast. With Raindrop 2.0 (Self-Healing Agents), the loop closes itself: your coding agent fixes it, and the fix becomes an eval to prevent regressions. Why It Matters AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. But AI agents fail silently, leaving engineers with almost no visibility into how their agents are actually performing. The current status quo is sifting through millions of logs and trying debug flaky evals that just aren't matching real world results. Evals are like unit tests, they confirm your model got specific test cases right. But in the real world agents call thousands of tools, run for hours, and encounter millions of unpredictable actions. That’s where Raindrop comes in. It learns the unique shape of each AI agent’s issues. Starting from presets like Laziness, Forgetting, or Task Failure, to automatically tuning itself to each agent and discovering unknown unknowns. With one click of a button, AI engineers start tracking issues or topics across 100% of their production data. They can see frequency over time, how many users are affected, relevant properties and more. In order to process hundreds of millions of events, we gradually train small, custom models, private to each company, that learn to uniquely understand how their product is used. As part of the early team, you’ll play a fundamental role in shaping the company - from making strategy and product decisions, to helping scale the team, to shaping the future of AI agents. Our Investors We’re backed by incredible investors including Lightspeed and leading AI companies including Figma Ventures, Vercel Ventures, founders of Replit (Amjad Masad and Michele Castata), Cognition (Walden Yan), Framer (Koen Bok and Jorn van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more. Your Focus Build out world-class infrastructure - servicing millions of requests a day + growing. Architect, implement, and scale the application Quick iteration without compromising on quality Deeply understand the customer Ideal Candidate Knows how to balance short-term and long-term speed Proven experience scaling applications Interest in AI products + tools (ideally experience building these or an avid user) Growth mindset Willing to do whatever it takes to solve a problem Must be in person in San Francisco (or willing to move) Apply now Other jobs at Raindrop Sales Development Representative San Francisco, CA, US Full-Time $70K - $110K 0.05% - 0.15% 1+ Years View job Account Executive San Francisco, CA, US Full-Time $120K - $140K 0.08% - 0.22% 6+ Years View job Forward Deployed Engineer (FDE) San Francisco, CA, US Full-Time $130K - $200K 3+ Years View job Founding Recruiter San Francisco, CA, US Full-Time $150K - $200K 0.10% - 0.50% 3+ Years View job Security Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 6+ Years View job Hundreds of YC startups are hiring on Work at a Startup. Sign up to see more › Work at a Startup Jobs Internships Events How it works Sign in Y Combinator About YC Press Privacy & Terms Contact Jobs by Role Software Engineer Jobs Design & UI/UX Jobs Product Manager Jobs Sales Jobs Marketing Jobs Support Jobs Operations Jobs Jobs by Location Software Engineer Jobs in San Francisco Product Manager Jobs in San Francisco Software Engineer Jobs in New York Product Manager Jobs in New York Software Engineer Jobs in Los Angeles Product Manager Jobs in Los Angeles Remote Jobs Remote Software Engineer Jobs Remote Design & UI/UX Jobs Remote Product Manager Jobs Remote Sales Jobs Remote Marketing Jobs Remote Support Jobs Remote Operations Jobs

Listed by Raindrop for a position based in the United States. Employers on this board attest they are hiring domestically.

Engineering

216 days ago

Product Engineer

Raindrop · San Francisco, CA, US

Pay

$150k–250k

Setting

On-site

Apply Sign in to favorite Permalink

Work at a Startup Startup Jobs Resume Review Education How it Works Log In Product Engineer at Raindrop(W24) $150K - $250K • 0.10% - 1.50% Sentry for AI Agents San Francisco, CA, US Full-time US citizen/visa only 3+ years Node.js Python TypeScript Torch/PyTorch Prompt Engineering Apply now About Raindrop Monitor your AI app the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI products. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast. About the role Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100s and the fastest-growing AI companies (Vercel, Speak, Clay) use it to catch silent failures in production. When an agent misbehaves, Raindrop alerts the team, links to the trace, and surfaces the root cause so they can fix it fast. With Raindrop 2.0 (Self-Healing Agents), the loop closes itself: your coding agent fixes it, and the fix becomes an eval to prevent regressions. Why It Matters AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. But AI agents fail silently, leaving engineers with almost no visibility into how their agents are actually performing. The current status quo is sifting through millions of logs and trying debug flaky evals that just aren't matching real world results. Evals are like unit tests, they confirm your model got specific test cases right. But in the real world agents call thousands of tools, run for hours, and encounter millions of unpredictable actions. That’s where Raindrop comes in. It learns the unique shape of each AI agent’s issues. Starting from presets like Laziness, Forgetting, or Task Failure, to automatically tuning itself to each agent and discovering unknown unknowns. With one click of a button, AI engineers start tracking issues or topics across 100% of their production data. They can see frequency over time, how many users are affected, relevant properties and more. In order to process hundreds of millions of events, we gradually train small, custom models, private to each company, that learn to uniquely understand how their product is used. As part of the early team, you’ll play a fundamental role in shaping the company - from making strategy and product decisions, to helping scale the team, to shaping the future of AI agents. Our Investors We’re backed by incredible investors including Lightspeed and leading AI companies including Figma Ventures, Vercel Ventures, founders of Replit (Amjad Masad and Michele Castata), Cognition (Walden Yan), Framer (Koen Bok and Jorn van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more. Your Focus Build out a world-class product - servicing millions of requests a day + growing. Architect, implement, and scale the application Quick iteration without compromising on quality Deeply understand the customer Ideal Candiate Knows how to balance short-term and long-term speed Proven experience scaling applications Interest in AI products + tools (ideally experience building these or an avid user) Growth mindset Willing to do whatever it takes to solve a problem Cares about building well-designed products Must be in person in San Francisco (or willing to move) Apply now Other jobs at Raindrop Sales Development Representative San Francisco, CA, US Full-Time $70K - $110K 0.05% - 0.15% 1+ Years View job Account Executive San Francisco, CA, US Full-Time $120K - $140K 0.08% - 0.22% 6+ Years View job Forward Deployed Engineer (FDE) San Francisco, CA, US Full-Time $130K - $200K 3+ Years View job Founding Recruiter San Francisco, CA, US Full-Time $150K - $200K 0.10% - 0.50% 3+ Years View job Security Engineer San Francisco, CA, US Full-Time $150K - $250K 0.10% - 1.50% 6+ Years View job Hundreds of YC startups are hiring on Work at a Startup. Sign up to see more › Work at a Startup Jobs Internships Events How it works Sign in Y Combinator About YC Press Privacy & Terms Contact Jobs by Role Software Engineer Jobs Design & UI/UX Jobs Product Manager Jobs Sales Jobs Marketing Jobs Support Jobs Operations Jobs Jobs by Location Software Engineer Jobs in San Francisco Product Manager Jobs in San Francisco Software Engineer Jobs in New York Product Manager Jobs in New York Software Engineer Jobs in Los Angeles Product Manager Jobs in Los Angeles Remote Jobs Remote Software Engineer Jobs Remote Design & UI/UX Jobs Remote Product Manager Jobs Remote Sales Jobs Remote Marketing Jobs Remote Support Jobs Remote Operations Jobs

Listed by Raindrop for a position based in the United States. Employers on this board attest they are hiring domestically.

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