About Gray Swan Gray Swan protects organizations from emerging AI security threats. We build real-time threat detection, automated validation, and adaptive defenses for AI labs and enterprises. We’re a team of ~30 people, well-funded, and growing fast.

We have strong traction and globally recognized customers, which means employees here take on real responsibility and meaningful equity from day one. This is a high-ownership environment where you’ll work on hard problems, move quickly, and help shape both the product and the company.

Many people join Gray Swan because our mission matters. We’re doing practical, high-impact work in AI safety, that sense of purpose is a core reason why engineers and researchers choose us.

Learn More About How We Work. The Role

The Go-To-Market (GTM) Engineer builds & owns the systems, data, and processes that power revenue generation across sales and marketing. This role is the connective tissue between pipeline creation and revenue conversion—ensuring that tooling, reporting, and workflows are reliable, scalable, and decision-grade.

We’re looking for a technical operator and builder who can move comfortably between HubSpot architecture, enrichment pipelines, internal tools, workflow automation, SQL, APIs, AI-assisted research, and deal operations. You’ll help us keep our CRM fresh, our pipeline clean, our dashboards decision-grade, and our GTM motion fast without creating unnecessary SaaS sprawl or operational debt.

You’ll also help us dogfood Gray Swan’s own products, including Cygnal and Shade , within our sales and customer-facing workflows so that our GTM motion reflects the same AI security standards we bring to customers.

What You’ll Do: Build and Automate GTM Systems

• Own and improve our GTM systems architecture, with HubSpot as the core CRM.
• Build workflows for enrichment, routing, scoring, account research, CRM hygiene, and pipeline management.
• Create automations using tools such as HubSpot, LLMs, APIs, webhooks, SQL, Google Sheets, and lightweight scripts.
• Build “headless” or internal workflows where they can replace unnecessary SaaS tools.
• Ensure GTM data is clean, structured, and useful for reporting and decision-making.

Build AI-Native GTM Workflows

• Design and maintain LLM-powered workflows for account research, call summaries, CRM updates, personalization, and deal hygiene.
• Evaluate AI-generated outputs for accuracy, usefulness, personalization quality, and failure modes.
• Build workflows that move insights from tools like Fireflies into HubSpot and other GTM systems.
• Create bots, agents, or automations that flag stale deals, missing fields, next-step gaps, renewal risks, and pipeline inconsistencies.

Own Deal Operations Infrastructure

• Build systems for proposal generation, pricing workflows, deal desk review, approvals, and contract reconciliation.
• Help unify deal data across HubSpot, Google Drive, call transcripts, proposals, pricing calculators, and signed agreements.
• Build internal tools such as pricing calculators for Shade and Cygnal, renewal health scoring, pipeline hygiene bots, and deal desk dashboards.
• Improve reporting across new business, expansion, renewals, and strategic accounts.

Support Revenue Operations and Reporting

• Maintain pipeline stages, lifecycle definitions, attribution logic, and CRM hygiene.
• Build dashboards for pipeline, conversion, forecasting, campaign performance, and revenue efficiency.
• Analyze funnel performance and identify operational bottlenecks.
• Partner with Leadership on forecasting, pipeline coverage, and GTM planning.

Dogfood Gray Swan Products

• Identify practical ways to use Cygnal and Shade in our own GTM workflows.
• Partner with Product and Sales to surface internal use cases, product feedback, and customer-facing examples.
• Help ensure our sales motion reflects the same AI security standards we bring to customers.

Who You Are:

• 3–5 years in GTM Engineering, RevOps, Sales Ops, or Marketing Ops in a B2B SaaS environment
• Strong Hubspot experience and understand CRM architecture, workflows, reporting, pipeline hygiene, and lifecycle stages.
• Strong analytical capability (Excel/Sheets + BI tools like Looker, Tableau, or Mode + AI tools for data, analytics, and reporting)
• Experience using SQL or database-style querying, and webhooks, no-code/low-code tools, and lightweight automation.
• Deep knowledge of AI tools or LLMs to improve research, data quality, automation, analytics, or workflow execution.
• Experience designing GTM processes (lead routing, scoring, pipeline stages)
• High attention to data integrity and system scalability

Bonus Points:

• Experience with Python or another scripting language.
• Experience with Clay, Apollo, ZoomInfo, Lusha, Chili Piper, LeanData, Default, Fireflies, Gong, Retool, Zapier, Make, or similar tools.
• Experience building internal tools with Claude Code, Cursor, Replit, or similar AI coding tools.
• Experience with ABM, sequencing, AI SDR tooling, enrichment pipelines, CPQ, pricing operations, or deal desk workflows.
• Experience in B2B SaaS, cybersecurity, AI, infrastructure, or technical enterprise sales.

If you don’t meet 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.

You’ll Thrive Here If You Are:

• A builder who prefers solving root problems over manually patching the same issue every week.
• Technical enough to work independently across systems, but collaborative enough to bring stakeholders along.
• Excited to use AI tools thoughtfully and evaluate where they create leverage.
• Comfortable operating in ambiguity and building from partial structure.
• Energized by helping a fast-growing startup build durable GTM systems before scale breaks them.
• Low ego, high ownership—willing to go from strategy to execution
• Strong cross-functional communicator

Compensation & Benefits:

We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.

Salary: $115,110 - $173,100

Equity: Competitive equity package

Benefits:

• 401k with up to 4% matching
• 28 days annual leave (vacation + holidays)
• Health, dental, and vision coverage
• Catered lunches (Pittsburgh office)
• Flexible work arrangements
• Visa sponsorship available for exceptional candidates

Interview Process:

• 🔎 Application review. We read everything; we’ll respond within Xdays.
• 🗣 Intro call (30 min). We learn about you; you learn about us.
• 🧑‍💻 Technical interview (90min). Brief description of format: no whiteboarding, take-home, etc.- 🗣 Experience & culture interview (60 min). Conversational exploration of the skills fit.
• 😇 Reference checks. We’ll reach out to 2 references that you provide.
• 📃 Offer. If it’s mutual, we move fast.

Compensation Range: $115K - $173K