Clearly AI

About Clearly AI Clearly AI automates the most painful bottleneck in the enterprise: security and privacy reviews. We help security teams complete high-quality threat models, privacy impact assessments, and vendor risk evaluations in minutes instead of weeks. We're live with Fortune 500s and global brands including Rivian, Ericsson, HID Global, Affirm, Webflow, and Okta. We've reviewed thousands of security-critical products, from badge scanners to stablecoin platforms to autonomous driving features. Backed by Y Combinator, Basis Set Ventures, Crosspoint Capital, Argon Ventures, and Ritual Capital. Selected as a Top 10 Finalist for the RSAC 2026 Innovation Sandbox Contest. Location Seattle/SF preferred, remote OK. We meet in person 1-2x per quarter. Applicants must be authorized to work in the United States without the need for visa sponsorship now or in the future. Why This Role Exists We've proven we can land and expand inside some of the world's most demanding security organizations. Now we need to scale it. We are looking for someone who has sold deeply technical security products into enterprise buying committees, knows what it takes to move a CISO org from curious to committed, and has the range to operate at both the deal level and the function-building level. You will be the first dedicated sales hire, with a direct line to the founders and ownership of everything that directly touches revenue: enterprise sales, account strategy, and channel partnerships. The right person has done this before, has the relationships and credibility to open doors fast, and is energized by the challenge of building something from a strong foundation. What You'll Own 1. Enterprise Sales Own the full sales cycle from first conversation to signed contract on enterprise deals across the CISO org, AppSec, GRC, and privacy functions Navigate complex buying committees with multiple technical and business stakeholders, including product security and third party risk teams Run organized, disciplined account-based selling with structured account plans, executive engagement strategies, and clear next steps at every stage, following common methodologies like MEDDPICC Build and manage a healthy pipeline with enough coverage to hit targets and enough visibility to forecast accurately 2. Account Strategy and Expansion Develop account plans for our existing customer base that identify expansion surface area and map the right stakeholders to the right opportunities Partner with the implementation and customer success teams to turn adoption into revenue Track account health signals and act on them before they become risks Bring the voice of the customer back into product and GTM conversations with enough structure that it actually changes decisions 3. Channel and Partner Development Build and manage relationships across the partner ecosystem: VARs, MSSPs, GSIs, and technology alliances Identify partners that can open doors into accounts we can't reach directly and structure the right engagement model for each Develop early partner relationships into repeatable co-sell motion as we scale 4. GTM Collaboration Work closely with marketing on account targeting, messaging, and campaign feedback so that outbound and inbound efforts compound rather than conflict Partner with product on the feedback loop between field conversations and roadmap decisions Stay deeply engaged in the market: tracking how the competitive landscape is shifting, how buyers are talking about the problem, and what signals are showing up in deals, and bring that intelligence back to product, marketing, and leadership in a form that actually influences decisions on pricing, positioning, and roadmap Own the sales playbook: what works, what doesn't, and what the next hire will need to succeed Use AI tools actively to increase your output across research, outreach personalization, and pipeline management, and stay current on how that landscape is evolving What This Role Is NOT Not a far

About Clearly AI Clearly AI automates the most painful bottleneck in the enterprise: security and privacy reviews. We help security teams complete high-quality threat models, privacy impact assessments, and vendor risk evaluations in minutes instead of weeks. We’re live with Fortune 500s and global brands including Rivian, Ericsson, HID Global, Affirm, Webflow, and Okta. We’ve reviewed thousands of security-critical products, from badge scanners to stablecoin platforms to autonomous driving features. Backed by Y Combinator, Basis Set Ventures, Crosspoint Capital, Argon Ventures, and Ritual Capital. Selected as a Top 10 Finalist for the RSAC 2026 Innovation Sandbox Contest. Advised by former CISOs of Amplitude and OKX, the former CEO of Reddit, and the former CPO of Brex. We are early. We are deeply technical. We are building alongside real practitioners, and we want a real practitioner who loves working with customers to help. We need a founding Product Manager who will own product the way a founder does. Why This Role Exists We’re hiring a Head of Product to own Clearly AI’s roadmap end-to-end, working with our founders to align product strategy against many competing needs from our enterprise customers and set the long-term vision.  You’ll lead design, discovery, experimentation, and delivery across a repeatable product lifecycle that you will be designing and implementing - partnering closely with Engineering, security SMEs, and the GTM team to translate the feedback from our customers into real, production-level value that solve their problems. At this stage, product and GTM/distribution are not separate problems; we need to figure out what to build, at the right time, in such a way that we continue to hold strong product-market-fit and a vision we can confidently grow towards.  We're a team of 10 with no product function today. You'd be building it from scratch. What You'll Own 1. Product Vision & Leadership Set the full product roadmap, aligning with the GTM and founding team to build things that matter Develop and own the framework for how we justify what is and isn't on roadmap, how it's resourced, and how we measure success of those investments and their impact on the business Establish scalable, repeatable product processes that grow with Clearly - this is the first product hire and comfort defining how to build things well is a must You've shipped AI that practitioners deeply love - you know how to design trust into the product, build guardrails from day one, make the call on when humans stay in the loop, and categorize LLM failure modes to target improvements You've set early product process and hired or grown product development teams 2. Customer Discovery A customer-first mindset - you’d rather talk to a customer than read a report, and you have experience building feedback loops that identify opportunities across multiple customers Run weekly conversations with security practitioners at our customers and prospects Aggregate feedback across every customer touchpoint, from support tickets to implementation calls. Embed in real review workflows  sit in on threat models, observe DPIA reviews, watch how the Jira ticket actually gets written Turn that fieldwork into crisp written product specs backed by "we asked five customers and they said X". Figure out what success means: through sales metrics, customer conversations, user usage, AI success/failure modes, etc. Develop training materials and serve as the internal authority on the product (what it does, what’s coming, what launched) You’ve found creative ways to get enterprise pilots off the ground, defined what success looks like, and turned early wins into a case for going broader or deeper 3. Engineering Partnership Write specs that engineers want to read Enough technical fluency to hold your own - you've owned technical products, have experience in ML/AI, and/or can talk to engineers without a translator. Engineering, Comp Sci, or related degree is a bonus.

About Clearly AI Clearly AI automates the most painful bottleneck in the enterprise: security and privacy reviews. We help security teams complete high-quality threat models, privacy impact assessments, and vendor risk evaluations in minutes instead of weeks. We're live with Fortune 500s and global brands including Rivian, Ericsson, HID Global, Affirm, Webflow, and Okta. We've reviewed thousands of security-critical products, from badge scanners to stablecoin platforms to autonomous driving features. Backed by Y Combinator, Basis Set Ventures, Crosspoint Capital, Argon Ventures, and Ritual Capital. Selected as a Top 10 Finalist for the RSAC 2026 Innovation Sandbox Contest. Advised by former CISOs of Amplitude and OKX, the former CEO of Reddit, and the former CPO of Brex. We are early. We are deeply technical.  We are building alongside real practitioners, and we want a real practitioner who loves working with customers to help. Our customers run security-critical workflows inside complex enterprise environments, and when something breaks they expect an answer that actually fixes it, not a status page. Why This Role Exists Our customers are security practitioners at Fortune 500s. They deploy Clearly AI alongside Jira, ServiceNow, Confluence, and GitHub, and they push the product hard in environments where stakes are real. When a review stalls, an integration drifts, or a model output looks off, they need a technical human on the other end who can dig in, find the root cause, and close the loop fast. We need a Support Engineer who owns the customer-facing technical interface end-to-end: triage, debug, fix or escalate, ship the doc that prevents the next one. This role exists to ensure customers feel taken care of, and to give engineering back their build time. What You'll Own 1. Customer Issue Resolution Own inbound issues from first message to verified resolution Reproduce, diagnose, and explain what's actually happening, both internally and to our customers Triage severity honestly and set expectations customers can plan around Be the person customers want on the thread when something is broken 2. Debug & Root Cause Analysis Read logs, traces, API responses, and model outputs to find the actual cause, not the surface symptom Use SQL and internal tooling to verify hypotheses before pulling engineering in Reproduce integration issues across Jira, ServiceNow, GitHub, and Confluence Write up root cause clearly enough that engineering can ship the fix without a follow-up call 3. Bug Triage & Engineering Handoff File bugs in Linear that engineers want to pick up: clear repro, scoped impact, suggested area Distinguish between one-off customer config issues and systemic product gaps Surface patterns across tickets that should become roadmap conversations Close the loop with customers the moment a fix ships 4. Support Infrastructure & Documentation Build the runbooks, internal docs, and customer-facing help content that prevent the next ticket Set up the tooling, dashboards, and alerting that make support a system rather than a scramble Define and track the metrics that matter (first response, time to resolution, reopen rate) Make the support function legible enough that the next hire can ramp in weeks, not months 5. Customer Trust Communicate with the calm specificity that earns practitioner trust Stay close to customers between incidents : know their workflows, their integrations, their pet peeves Make every interaction feel like the customer is the most important account we have, because they are What This Role Is NOT Not a ticket-closing queue role. You'll own outcomes, not volume Not a generalist help desk, every issue is technical Not Customer Success or Sales Not isolated from engineering; you'll sit inside the build loop What We're Looking For Required 3+ years in a technical support engineering, security engineering, forward-deployed engineering, SRE, or similar customer-facing technical role Comfortable reading c

About Clearly AI Clearly AI automates the most painful bottleneck in the enterprise: security and privacy reviews. We help security teams complete high-quality threat models, privacy impact assessments, and vendor risk evaluations in minutes instead of weeks. We’re live with Fortune 500s and global brands including Rivian, Ericsson, HID Global, Affirm, Webflow, and Okta. We’ve reviewed thousands of security-critical products, from badge scanners to stablecoin platforms to autonomous driving features. Backed by Y Combinator, Basis Set Ventures, Crosspoint Capital, Argon Ventures, and Ritual Capital. Selected as a Top 10 Finalist for the RSAC 2026 Innovation Sandbox Contest. Advised by former CISOs of Amplitude and OKX, the former CEO of Reddit, and the former CPO of Brex. We are early. We are deeply technical. We are building alongside real practitioners, and we want a real practitioner who loves working with customers to help. Why This Role Exists Our customers are Fortune 500s and global brands operating inside complex, highly regulated security environments. They need someone who can: Understand real security workflows across threat modeling, privacy, and vendor risk Integrate Clearly AI into those workflows alongside Jira, ServiceNow, Confluence, and GitHub Drive disciplined implementation from contract to production Translate deployment friction into shipped product improvements This role exists to ensure customers deploy Clearly AI deeply, correctly, and measurably. What You’ll Own 1. Technical Deployment & Production Adoption Lead end-to-end onboarding from signed contract → operational production usage Integrate Clearly AI into enterprise systems (Jira, ServiceNow, Confluence, GitHub, etc.) Configure review workflows aligned to each customer’s security processes Drive implementation timelines and ensure milestones are met Move customers from pilot → embedded operational usage 2. Implementation Project Management Run structured weekly and monthly customer syncs Maintain clear agendas, owners, and next steps Track blockers and technical dependencies Coordinate closely with engineering on integration requirements Ensure nothing drifts between calls 3. Security Workflow Optimization Operate inside real threat modeling, DPIA, and vendor risk workflows Identify automation opportunities within existing processes Help reduce review cycle time and operational backlog Ensure product usage maps to measurable security outcomes 4. Product Feedback & Engineering Collaboration Conduct structured deployment reviews Translate workflow friction into actionable feature requests Log and manage feedback clearly in Linear Collaborate directly with engineering on requirements and edge cases Close the loop with customers when improvements ship 5. Support & Process Infrastructure Help triage inbound customer support issues Identify recurring patterns in bugs or workflow friction Build lightweight processes for tracking blockers and feature requests Create documentation and onboarding playbooks What This Role Is NOT Not a traditional SaaS Customer Success Manager Not primarily an executive relationship role Not a quota-carrying sales position Not a broad CS team builder What We’re Looking For Required 2+ years in GRC, privacy, or security engineering or as a security consultant Hands-on experience with threat modeling, vendor risk assessments, or privacy reviews Experience implementing security tools into enterprise workflows, setting up integrations, and configuring tooling Strong cross-functional project management skills Ability to speak the language of security practitioners (STRIDE, DPIA, TPRM, CVE, etc.) Experience working closely with Product and Engineering teams Ability to debug customer issues to identify root causes Strongly Preferred Prior experience as a forward deployed engineer or security consultant Deep familiarity with modern security workflows (AppSec reviews, privacy programs, vendor risk programs) Experience

About Clearly AI Clearly AI automates the most painful bottleneck in the enterprise: security and privacy reviews. We help security teams complete high-quality threat models, privacy impact assessments, and vendor risk evaluations in minutes instead of weeks. We're live with Fortune 500s and global brands including Rivian, Ericsson, HID Global, Affirm, Webflow, and Okta. We've reviewed thousands of security-critical products, from badge scanners to stablecoin platforms to autonomous driving features. Backed by Y Combinator, Basis Set Ventures, Crosspoint Capital, Argon Ventures, and Ritual Capital. Selected as a Top 10 Finalist for the RSAC 2026 Innovation Sandbox Contest. Location Seattle/SF preferred, remote OK. We meet in person 1-2x per quarter. Applicants must be authorized to work in the United States without the need for visa sponsorship now or in the future. Why This Role Exists We've proven we can land and expand inside some of the world's most demanding security organizations. Now we need to build the machine that scales it. This is not a RevOps generalist role or a traditional marketing ops hire. We're looking for someone who thinks like an engineer and operates like a strategist - someone who can design and build an AI-native GTM engine from scratch, then draw the insights that tell us what's actually working. The right person has built real systems, written real code, and has strong opinions about how AI changes what's possible in go-to-market. You'll be the first person in this function, with a direct line to founders and a greenfield mandate. What You'll Own 1. GTM Stack Architecture & Build Design and implement our full GTM tech stack from the ground up - CRM, marketing and sales automation, data enrichment, and signal capture Evaluate, select, and integrate best-in-class tools for our motion (enterprise, security-focused, low-volume/high-ACV) Build for extensibility: every system should connect cleanly to the next Own the data model and ensure clean, consistent data flows across the stack 2. AI-Native GTM Automation Design and deploy AI-powered workflows that automate research, outreach personalization, lead scoring, and pipeline hygiene Build agents and automations that let our small GTM team punch far above its weight Stay current on the rapidly evolving AI tooling landscape and make smart adoption decisions Avoid bloat: build systems that are powerful but maintainable 3. Revenue Intelligence & Insight Generation Instrument our full funnel intelligence. From first touch through expansion - to surface what's actually driving revenue Build and evolve dashboards and reporting frameworks that let leadership make fast, informed decisions Identify patterns in win/loss data, pipeline velocity, and product usage that inform GTM strategy Partner with GTM leadership to translate data into clear recommendations, not just charts 4. Demand Generation Infrastructure Build and maintain the systems that support outbound and inbound at scale Implement intent data, enrichment, and account scoring that helps us find and prioritize the right buyers Ensure our outreach infrastructure (deliverability, sequencing, personalization) is built to enterprise standards Support campaign execution with the tooling and automation it needs to work 5. Website & Conversion Infrastructure Own the GTM layer of our website - CMS enhancement, chat and conversion tooling, form routing, and visitor intelligence Deploy and configure chat and lead capture tooling (e.g., Qualified, Drift, or similar) connected to CRM and routing logic Instrument the site for intent signals - who's visiting, what they're reading, and how that maps to pipeline Ensure website systems and related data connect cleanly to the broader GTM stack 6. Cross-Functional Collaboration Work directly with GTM teams and leadership to understand what's slowing deals down and build tools that fix it Partner with the Technical Implementation and Engineering teams to connect pr

About Clearly AI Clearly AI automates security and privacy reviews with AI. We built the product we wish we had after performing hundreds of reviews at Amazon and Moveworks, and today our users complete reviews in minutes instead of days. Clearly AI helps engineering teams ship faster by automating security and privacy reviews. Companies like Rivian, HID Global, and Affirm use Clearly AI to cut review times from weeks to minutes. We’re building a new kind of AI workspace designed to help security, privacy, and compliance experts meet high standards in regulated enterprises. We’re a fast-growing YC startup with enterprise customers who depend on us to stay secure and compliant without slowing down. As our founding UX/UI design engineer, you’ll shape the product experience end-to-end and set the design bar for everything that follows. Role Description Full-time, Sr Software Engineer at Clearly AI. You will be responsible for designing and developing enterprise-grade full-stack AI B2B SaaS web apps. Given the size and stage of our startup, you will take responsibility over significant portions of the product. Location Seattle/SF preferred, remote OK. We meet in person 1-2x per quarter. Applicants must be authorized to work in the United States without the need for visa sponsorship now or in the future. Qualifications 5-7+ years of professional experience developing software. Willingness to work directly with users and prioritize their needs over our internal dev experience. Strong proficiency in Typescript, NextJS, modern Python toolchain (uv, ruff, ty, etc.). A love of type safety, coding discipline. Plus: deep knowledge of integrations, oauth2, abac, infra-as-code, agent sandboxes, security, AWS, CDK, the quirks of each of the major LLM APIs, Convex, building for enterprise customers, security and privacy assessments. Bonus: ability to recite the entirety of Designing Data Intensive Applications in reverse.

Founding UI/UX Design Engineer Seattle / Remote | Full-Time About Clearly AI Clearly AI automates security and privacy reviews with AI. We built the product we wish we had after performing hundreds of reviews at Amazon and Moveworks, and today our users complete reviews in minutes instead of days. Clearly AI helps engineering teams ship faster by automating security and privacy reviews. Companies like Rivian, HID Global, and Affirm use Clearly AI to cut review times from weeks to minutes. We’re building a new kind of AI workspace designed to help security, privacy, and compliance experts meet high standards in regulated enterprises. We’re a fast-growing YC startup with enterprise customers who depend on us to stay secure and compliant without slowing down. As our founding UX/UI design engineer, you’ll shape the product experience end-to-end and set the design bar for everything that follows. The Role Everyone talks about 10x engineers but the real risk for most companies is not whether you can build it, it’s if you’re building the right thing. We want designers that can distill why a user is adopting and then prototype the most clear version of that insight. Our users want to work with you. Our users are subject matter experts at global enterprises. Our users have high standards and demand the best. You will have ownership. You will exercise taste. You will deliver excellence. You will experience the joys of building something appreciated by grumpy, picky users. What You’ll Do Own our entire product front-end from high-level information architecture to final implementation Design and refine user journeys across Clearly’s product, ensuring intuitive flows for technical and non-technical users alike Create and enforce UX requirements and design standards Continuously improve usability, reduce friction, push performance Monitor product usage via implicit and explicit signals Collaborate closely with founders What We’re Looking For Requirements 5+ years of experience in UI/UX design for web applications, ideally for B2B SaaS Strong frontend engineering skills, including proficiency in TypeScript, React, and modern CSS frameworks such as Tailwind Proven ability to take products from low-fidelity concepts to polished, production-ready interfaces Experience building design systems or component libraries for consistency and scalability A data-informed mindset and comfort analyzing user behavior and soliciting feedback directly from our customers Startup DNA: thrives in ambiguity, moves fast, and loves crafting from 0 to 1 Experience designing entirely new products Figma-to-code workflows or other rapid prototyping methods Interest in security, privacy, or developer tools