Location: New York City (5 days/week in office)

About Thoughtly

Thoughtly is a breakout, high-growth, post-seed SaaS startup backed by top-tier investors. We’re scaling fast with enterprise customers and building the future of enterprise GTM through AI-powered voice automation. We’ve proven incredible product-market fit, we’re growing ARR at a category-defining pace, and we’re now preparing to scale from ~$1M ARR to $50M+ over the next 24 months.

Role Overview

We’re looking for a Head of GTM to lead and scale the entire revenue organization — Growth, Sales, Customer Success, and Pipeline Operations. This is a founding leadership role with direct accountability for ARR growth, ACV expansion, onboarding efficiency, and NRR.

You’ll bring deep B2B SaaS leadership experience — having scaled a team from ~$1M ARR through $50M ARR+ — and you’ll thrive in our in-office, high-tempo NYC environment. This is an opportunity to take a category-defining product, proven in enterprise environments, and build the systems, talent, and processes that define our next stage of growth.

Key Responsibilities

• Own the GTM strategy for Growth, Sales, CS, and Pipeline; align all functions to ACV step-ups, NRR lift, and onboarding efficiency.
• Build and lead a high-performing team of AEs, AMs, CSMs, and Growth operators; grow from 4 to 12+ heads in 12 months.
• Drive a scalable sales motion: higher price floors, multi-stakeholder deals, and value-based expansion.
• Establish and operationalize: daily standups, weekly pipeline and experiment reviews, KPI-driven dashboards, and post-mortems.
• Partner with Product to align GTM insights with roadmap, ensuring enterprise buyers’ needs are met.
• Build repeatable expansion playbooks to maximize NRR and land-and-expand velocity across enterprise accounts.
• Own forecasting, planning, and reporting; partner with Finance/Ops for board-ready instrumentation and KPI reporting.
• Represent Thoughtly externally: enterprise prospects, partners, and at key events.

What We’re Looking For

• Proven GTM leadership: scaled a B2B SaaS GTM org from ~$1M ARR to $50M+ ARR.
• Strong experience in enterprise software — ideally with call center, workflow automation, or platform integration products.
• Deep understanding of enterprise sales mechanics: multi-threaded sales cycles, ROI-driven proposals, and complex procurement.
• Ability to build repeatable, scalable systems for growth, pipeline, and customer success.
• Hands-on operator: thrives in high-tempo environments, willing to get in the weeds to close key deals or run campaigns.
• Excellent people leader: proven record of hiring, coaching, and retaining top talent.
• Highly analytical: data-driven approach to forecasting, pipeline management, and performance tracking.

Compensation & Structure

• Competitive base salary
• Significant equity stake
• Direct executive leadership role reporting to the CEO

Why Join Now

• Lead GTM at one of the fastest-growing voice AI platforms in the world.
• Build and scale a team, motion, and revenue engine that defines a category.
• Shape the trajectory of a company scaling from ~$1M ARR to $50M+ ARR.