Role Description We are looking for a Senior AI Developer & Cloud Architect to design, build, and own the AI-powered compliance scraping engine and cloud infrastructure layer for an internal platform monitoring up to 70,000 credit card offer pages per month. This is a hands-on, sole-builder contractor role that sits at the intersection of cloud architecture, AI engineering, and large-scale web scraping, with a clear mandate: deliver a production-grade system that detects compliance violations across issuer offer pages with high accuracy and controlled token costs. You will do this by: - Architecting the AWS environment from the ground up. - Building a containerized worker fleet that integrates Playwright rendering with Claude-powered contextual analysis. - Defining clean API contracts with the internal team that owns the Laravel control panel. This is not a managed-PaaS or prototype role. You will be accountable for end-to-end delivery — architecture, build, documentation, and knowledge transfer — owning the full scraping and AI pipeline from URL intake through compliance findings, screenshot evidence, and results delivery back to the portal. Responsibilities - Design and configure the production AWS environment (ECS/Fargate, SQS, API Gateway, RDS PostgreSQL, S3, IAM, CloudWatch) using infrastructure as code (Terraform or CDK). - Build a stateless, containerized worker fleet that integrates Playwright-based page rendering, structured rule evaluation, and Claude API analysis. - Implement token optimization strategies across the LLM pipeline — prompt engineering, context pruning, caching, model selection, and batching — with measurable cost outcomes. - Define and document API contracts, job payload schemas, and database write patterns with the internal Laravel portal team to enable parallel development. - Build third-party API ingestion and field-level diff-detection logic that automatically adjusts monitoring rules when product data changes. - Handle modern web rendering challenges at scale: JavaScript-heavy SPAs, interstitials, cookie consent overlays, dynamic content, viewport switching, and full-page screenshot capture. - Evaluate when LLM analysis is the correct tool versus a classifier or rules-based approach, and design the two-stage rule-engine-plus-AI pipeline accordingly. - Build and maintain a unit test suite covering all modules and APIs to ensure uptime and proper functionality. - Document every architecture decision, configuration, API contract, and operational procedure continuously — not as a final-week deliverable. - Deliver a complete runbook and knowledge transfer to the internal team at engagement close. - Operate independently end-to-end while coordinating closely with the internal portal team and reporting directly to the Senior Director, surfacing risks and trade-offs early. Requirements - Production backend Python experience, including async patterns, type hints, packaging, and testing. - Direct production experience designing and configuring AWS ECS/Fargate, SQS, API Gateway, RDS (PostgreSQL), S3, IAM, and CloudWatch, with infrastructure as code (Terraform or CDK). - Real shipped systems calling the Anthropic Claude API in production, with demonstrated experience in prompt design, structured output, error handling, and cost trade-offs. - Demonstrated track record reducing token spend on production LLM workloads, with specific before/after results you can walk through. - Working knowledge of other LLM providers sufficient to recommend cheaper or better alternatives for specific tasks. - Production Playwright experience at scale, including headless Chromium failure modes, network idle detection, dynamic content handling, viewport switching, and screenshot strategy. Selenium or Puppeteer experience does not substitute. - Machine learning fundamentals sufficient to evaluate when LLM analysis is the right tool versus a classifier or rules-based approach, and to reason about evaluation and false-positive rates. - Docker and containerization experience, including image optimization, ECR, and stateless worker design. - Ability to operate fully independently — no engineering team underneath you — while documenting continuously and coordinating cleanly with an internal team. Nice to Have - Experience with API ingestion and field-level diff-detection systems. - Laravel or PHP familiarity, enough to coordinate cleanly on API contracts with the portal team. - SOC 2 Type II compliance experience. - Salesforce API integration experience. - Regulated-industry experience (financial services, healthcare, or insurance). Benefits - The expected hourly range for this position is $80/hr - 100/hr. This hourly range is an estimate, and the actual hourly rate may vary based on the Company’s compensation practices. - The hourly rate may be adjusted based on applicant's geographic location. - This position is eligible to participate in the Company’s standard employee benefits programs, which currently include health care benefits. Company Description QuinStreet is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, national origin, pregnancy status, sex, age, marital status, disability, sexual orientation, gender identity or any other characteristics protected by law. Please see QuinStreet’s Employee Privacy Notice here.

Additional Information All your information will be kept confidential according to EEO guidelines.

• Design, build, and maintain AI agents, integrations, and automations that reduce manual work, eliminate bottlenecks, and improve productivity across every department at Chipply. • Inspect Chipply's internal SaaS platforms (HubSpot, Microsoft 365, Confluence, Slack, and others) to understand what APIs, webhooks, and MCP connectors they expose, and use those surfaces to build the integrations each team needs. • Partner with leadership and department heads to identify and prioritize high-impact opportunities by mapping existing workflows and pinpointing where engineering effort — AI-powered or deterministic — will deliver measurable improvement. • Write production code. Build multi-tool and multi-agent systems that connect Chipply's internal platforms into seamless end-to-end processes. Make sound judgment calls on when AI is the right tool and when a deterministic solution is a better fit. • Build evals and monitoring for AI systems you ship, so output quality is measurable rather than assumed. • Serve as Chipply's internal AI champion by leading education, training, and adoption efforts, and by acting as the go-to engineering resource for AI questions, best practices, and emerging use cases. • Establish and maintain responsible AI governance, including guidelines for data handling, privacy, model and tool selection, output quality monitoring, and ethical use. • Continuously evaluate emerging AI tools, agent frameworks, model providers, and orchestration libraries; pilot promising technologies and recommend adoption decisions based on impact, cost, and fit. • Measure and report on the ROI of the systems you ship, tracking time saved, error reduction, cost impact, and quality improvements. • Develop and maintain documentation for the systems, integrations, and AI workflows you build so institutional knowledge scales with the company. • Serve as a liaison across Engineering, Finance, Sales, Marketing, Customer Support, and Product to align on technology needs and ship workflow improvements end to end. • Monitor security and compliance across the integrations and AI systems you build, collaborating with engineering and leadership to ensure data protection best practices are followed. • Continuously redefine the scope, priorities, and deliverables of the role as Chipply's needs and the broader AI ecosystem evolve.

Role Description You will be the strategic and technical owner of transformation engagements on a defined set of accounts. The most informed voice on what Pencil should do for each client and how the work gets done. You set the thesis, structure the engagement from first principles, co-design the recommendations and timelines with Forward Deployed Engineers and Creative Leads, lead the client through the enterprise-wide change required to make it stick, and stand behind quality and performance once the work ships. You own the recommendations and the narrative we tell our clients. Key Responsibilities: - Implementation Leadership: Own the narrative told to the client and the strategic and tactical plan that drives the engagement, setting the transformation thesis, co-designing the recommendations with Forward Deployed Engineers and Creative Leads. - Structured Problem-Solving: Take ambiguous client problems and structure them from first principles into a clear set of hypotheses, workstreams, and sequenced decisions everyone can act on. - Change Management Leadership: Lead clients through enterprise-wide transformation, moving them beyond siloed pilots into integrated, AI-driven workflows - navigating complex stakeholder landscapes, identifying blockers and champions, and engineering the buy-in that scaled AI adoption requires. - AI Process Design: Translate abstract GenAI concepts into clear, repeatable operating processes that client teams can execute confidently day-to-day. - Product Feedback Loop: Act as the voice of the customer internally, feeding insights back to Product and Engineering - what's missing, what's broken, what's worth doubling down on - so Pencil's roadmap stays enterprise-ready. - Transformation Blueprints: Codify what works on your accounts into repeatable Blueprints the rest of the team can run, so every successful engagement leaves behind a sharper playbook than the one before it. Qualifications - A strong academic record in a quantitative or analytical discipline - STEM, economics, engineering, or business. - Minimum of 5 years' experience in consulting, in-house transformation, programme management, or enterprise tech implementation. - AI-native in your day-to-day; experience with Claude Code or other agentic tooling is a strong plus. - Tech-fluent and hands-on; lightweight engineering - SQL, scripts, reading code - is a strong plus. - Confident with senior stakeholders; able to carry a client meeting and give direct feedback. - A track record of delivering complex, cross-functional, often ambiguous work to a high standard and on time. - Marketing, advertising, or agency experience helps, but it’s not what sets candidates apart. Requirements - Are Provocative and Brave: Challenge a customer’s existing way of working to help them avoid long-term implementation challenges. - Are an Ally to Change: Comfortable with ambiguity and change, helping others navigate the "new and unknown." - Believe in Enterprise Adoption: Obsessed with seeing technology move away from “pilot purgatory" towards an embedded, value-driving part of a company’s culture. - Embody Pencil Values: Lead with transparency, agility, and a focus on measurable impact. KPIs & Success Measures - Enterprise Adoption: Depth and breadth of Pencil usage across a customer's teams, departments, and use cases once the rollout is live. - Time-to-Value: Speed at which your accounts reach their first defined success metric or ROI milestone after engagement kickoff. - Quality of Transformation Narrative: How well your transformation thesis and the strategic and tactical planning survive delivery without major rework. - Product Feedback Impact: Quality and reach of insights fed back to Product and Engineering that keep Pencil's roadmap enterprise-ready. - Blueprint Contribution: Successful documentation and internal adoption of repeatable "Transformation Blueprints" based on customer wins. Benefits - 25 days PTO plus public holidays, with a Flexible Time Off scheme. - Health insurance / private medical cover. - Monthly stipend towards wellness, fitness, and learning and development. - Remote - work from anywhere in your home country. - Enhanced parental leave policies, whether you become a parent through birth, adoption, or surrogacy. - Access to our Pencil office in The Shard, London for UK employees. - Flexible working hours.