
Job Overview
Location
Pittsburgh
Job Type
Full-time
Category
Engineering
Date Posted
May 16, 2026
Full Job Description
📋 Description
- • Own and improve the Go-to-Market (GTM) systems architecture centered on HubSpot, ensuring CRM hygiene, pipeline integrity, and scalable workflows for sales and marketing operations.
- • Design and automate enrichment, routing, scoring, and account research workflows using HubSpot, LLMs, APIs, webhooks, SQL, Google Sheets, and lightweight scripts to eliminate manual processes and reduce SaaS sprawl.
- • Build AI-native GTM workflows that leverage LLMs for account research, call summarization, CRM auto-updates, personalization, deal hygiene, and flagging stale deals, missing fields, next-step gaps, or renewal risks.
- • Integrate insights from AI-powered tools like Fireflies into HubSpot and other GTM systems to automate data capture and improve decision-making accuracy.
- • Develop internal tools such as pricing calculators for Cygnal and Shade, renewal health scoring models, pipeline hygiene bots, and deal desk dashboards to standardize and streamline revenue operations.
- • Unify deal data across HubSpot, Google Drive, call transcripts, proposals, pricing calculators, and signed contracts to create a single source of truth for deal tracking and reporting.
- • Maintain and refine pipeline stages, lifecycle definitions, attribution logic, and CRM data standards to ensure reliable forecasting and revenue reporting.
- • Build and maintain dashboards for pipeline health, conversion rates, forecasting accuracy, campaign performance, and revenue efficiency to support leadership decision-making.
- • Analyze funnel metrics to identify operational bottlenecks and recommend data-driven improvements to GTM motion and conversion rates.
- • Partner with Sales, Product, and Leadership to align GTM processes with business goals, forecasting needs, and pipeline coverage targets.
- • Dogfood Gray Swan’s own products—Cygnal and Shade—within internal sales and customer-facing workflows to validate product effectiveness and surface real-world use cases.
- • Collaborate with Product and Sales teams to translate internal usage of Cygnal and Shade into customer-facing demonstrations, feedback loops, and security-aligned sales practices.
- • Ensure the company’s GTM motion reflects the same AI security standards applied to customer deployments, reinforcing product credibility and trust.
- • Evaluate AI-generated outputs for accuracy, personalization quality, and failure modes to maintain high data integrity and operational reliability in automated workflows.
- • Replace redundant SaaS tools with headless or internal automations to reduce costs, complexity, and technical debt in the GTM tech stack.
- • Support deal operations infrastructure including proposal generation, pricing workflows, deal desk reviews, approvals, and contract reconciliation processes.
- • Improve reporting across new business, expansion, renewals, and strategic accounts by standardizing metrics, automating data pulls, and enhancing visibility into revenue drivers.
- • Operate with high ownership in a fast-paced startup environment, building durable systems before scale creates operational friction.
- • Work independently across technical systems while maintaining clear communication with cross-functional stakeholders in Sales, Marketing, and Product.
- • Embrace ambiguity by building functional systems from partial structure, prioritizing root-cause solutions over manual patches.
- • Apply AI tools thoughtfully to augment research, data quality, analytics, and workflow execution without introducing bias or inaccuracies.
- • Maintain low ego and high ownership, moving seamlessly from strategy to execution across technical and operational domains.
Skills & Technologies
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About Gray Swan AI
Gray Swan AI is a technology company focused on developing and deploying artificial intelligence solutions. They specialize in creating AI-powered tools and platforms designed to address complex challenges across various industries. Their offerings often involve advanced machine learning, natural language processing, and data analytics to provide actionable insights and automate processes. Gray Swan AI aims to help organizations leverage the power of AI to improve efficiency, drive innovation, and gain a competitive edge. The company's approach typically involves a deep understanding of client needs to deliver tailored AI strategies and implementations that yield measurable results and foster long-term growth.
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