Clearly AI

Provide end-to-end technical support and root cause analysis for security-focused enterprise software integrations. | Requires 3+ years technical support experience, strong debugging skills, and customer-facing communication expertise. | 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 code, logs, SQL, and API traces to find root cause Strong written communication: your bug reports and customer replies are clear, specific, and free of filler Experience debugging integrations with enterprise systems (Jira, ServiceNow, GitHub, Confluence, or similar) High empathy for technical users under pressure, paired with the discipline to set realistic expectations Comfort with ambiguity and a track record of building process where there was none "Unreasonable Hospitality" energy: you take care of the people you support in detail, beyond what the job strictly requires Strongly Preferred Background in security, GRC, or privacy , or experience supporting security practitioners Light engineering chops , you can ship a small fix or script yourself when it's faster than waiting Early-stage startup experience where you drove direct customer impact How Success Is Measured (First 6 Months) Response and resolution times within established SLAs. Ideally with issues being proactively resolved before customer complaints Engineering protected from low-leverage support load, with clear escalation paths when their help is needed Bug reports filed at a quality that shortens engineering time-to-fix A documentation and runbook footprint that materially reduces repeat tickets Customer expansion and renewal conversations cite support quality as a reason to stay Why Join Clearly AI Sit at the closest possible distance to real customers solving real security problems Work directly with technical founders who treat support as a product surface, not a cost center Build the support function for an AI company defining a new enterprise category RSAC 2026 Innovation Sandbox Top 10 Finalist, backed by $8.4M in seed funding Operate at the intersection of frontier AI and enterprise security Competitive salary, meaningful equity, and benefits Direct path to leadership as the support function scales

| About Clearly AI Clearly AI accelerates enterprise security and privacy reviews. Our platform helps users complete threat models, privacy impact reviews, and vendor risk evaluations in a fraction of the time. We are a seed-stage company of security and AI experts backed by strong investors including Y Combinator, Basis Set Ventures, and Argon Ventures. You’ll be working closely with the founders and our rapidly-growing customer base, including leaders from Fortune 500s. The Role We’re hiring our first Customer Success Leader to ensure our customers achieve fast, measurable outcomes with Clearly AI and to lay the foundation for our CS function. This is a hands-on, high-impact role: you’ll partner with security, GRC and compliance leaders by optimizing their workflows and enabling them to adopt innovation more rapidly while building the processes, playbooks, and tools to maintain and grow customer relationships critical to our growth path. If you’re excited about building momentum and being the voice of the customer inside a fast-moving YC-backed startup, we’d love to meet you. What You’ll Do Own the post-sales journey: onboarding, training, adoption, renewals, and expansions Be a trusted advisor: guide CISOs, compliance, and security teams to achieve measurable ROI Build from scratch: create onboarding and success playbooks, customer resources, and health metrics Drive retention and growth: monitor account health, identify risks, and proactively manage renewals Shape our product: partner with Product/Engineering to bring customer insights directly into our roadmap Prepare for scale: establish key CS metrics and process, such as driving regular customer meetings, socializing future roadmap releases, and set the foundation for hiring as we expand Pre-sale POV support: take over the proof of value process and workflow, and integration mapping as Clearly proves organizational impact What We’re Looking For 5-8+ years in Customer Success, Account Management, or Consulting in B2B SaaS Proven experience managing senior customer stakeholders (ideally CISO, CIO, CPO, or equivalent) A builder’s mindset: excited to create structure and process in an early-stage environment Exceptional communication skills, able to translate technical security/AI concepts into clear business value Startup DNA: adaptable, resourceful, and energized by ambiguity Bonus Qualifications Background in security, compliance, or AI/ML-driven SaaS Experience with hands-on implementation and integrations (with products like ServiceNow, Jira, Google Drive) Experience with custom configurations and prompting based on customer needs Why Join Clearly AI? Be the founding Customer Success hire getting to define and scale the CS function Work with security and privacy leaders at cutting-edge companies YC alum with proven, technical founders and strong growth momentum Competitive salary, equity, and benefits Direct path to leadership opportunities as the company scales