GTM AI Specialist

The GTM AI Specialist designs, builds and runs the AI agents, automations and data syncs behind our go-to-market motion. You own three workstreams and the connective tissue between them: GTM AI, RevOps automation and support bots.

Role details

Reports to: Head of Customer Experience

Works with: Sales, Partnerships, Marketing, Customer Success, Support, Product, Engineering

Systems: HubSpot, ClickUp, Slack, Fellow.ai, help desk and chat, product data, partner APIs, Claude and other LLM tools

Primary outcomes: One synced customer record, less manual work for every GTM team, faster answers for customers, Keep HubSpot and ClickUp in two-way sync so pipeline, onboarding and account work live in one place.

• Automate reporting on pipeline, activation, TPV and retention so leaders get answers without building spreadsheets.

Support bots

• Design, train and tune AI support agents for firms, taxpayers and partners across chat, email and in-product help.

• Ground bots in our help center and SOPs, and set clear rules for when a bot hands off to a person.

• Review bot conversations weekly and close gaps in content and flows.

One cohesive lifecycle

• Map every customer touchpoint across headless systems, from first contact through remittance and renewal.

• Build the data layer and event syncs so each system sees the same customer, stage and history.

• Make sure a firm, taxpayer or partner gets a consistent experience whether they talk to a person, a bot or an automated message.

• Set guardrails for data privacy, accuracy and compliance in every AI workflow that touches payments or tax data., 1. First 30 days: map every lifecycle system, data flow and manual handoff. Deliver a prioritized automation roadmap.

1. First 60 days: HubSpot and ClickUp in two-way sync, lifecycle stages cleaned up, and the first support bot live on top questions.

2. First 90 days: GTM AI workflows in daily use by sales and CS, automated pipeline and retention reporting, and a single customer view across systems.

Ongoing KPIs: hours of manual work removed, bot resolution rate and handoff quality, CRM data accuracy, time from close to onboarding kickoff, and adoption of AI workflows by the GTM team.

4+ years in RevOps, GTM operations, marketing ops or support operations at a B2B SaaS or fintech company.

• Hands-on experience shipping AI agents or LLM workflows in production, including prompt design, retrieval and evaluation.

• Deep HubSpot admin skills: objects, properties, workflows, lifecycle stages and reporting.

• Experience building integrations and syncs with APIs, webhooks and tools like Zapier, Make, n8n or Workato.

• Working SQL and comfort with at least one scripting language such as Python or JavaScript.

• Experience setting up or running an AI support bot or help desk automation.

• Systems thinking: you see the whole customer journey and design data models that hold up as we scale.

• Clear writing and the ability to explain technical tradeoffs to sales, CS and leadership.

Nice to have

• Experience with ClickUp, Fellow.ai or similar project and meeting tools.

• Background in payments, fintech or tax and accounting software.

• Experience with MCP servers, agent frameworks or Claude-based tooling.

• Experience with a data warehouse or BI tool such as QuickSight.

• Experience as the first ops or AI hire at an early-stage startup.

$115,000-$135,000 base salary, plus a performance-based bonus.

Pay: $115,000.00 - $135,000.00 per year