Lindy Drope

Founding team at Lindy. Head of Sales. Building the future of work with AI.

$3.4M New ARR in 2025
47% of Company Revenue
80+ AI Agents Deployed

About

I'm a founding GTM hire and Head of Sales at Lindy, an AI agent platform — and the only GTM retained after the company pivot. In 2025, I closed $3.4M in new ARR, representing 47% of total company revenue during 650% YoY growth. I sold six-figure enterprise deals into CTOs, COOs, CROs, and CEOs across healthcare, tech, legal, and finance.

Deep technical background for a sales leader — I acted as Lindy's first forward-deployed engineer, personally building and deploying 80+ AI agents for enterprise customers. I work across Anthropic, OpenAI, and Gemini models daily, and build with Cursor and Claude Code.

Before AI, I was in enterprise sales at Cintas: 130–160% to quota, closing $117K–$300K ACV deals with 5–10 year contract terms. I sold into COOs and Heads of Facility Services across education, government, healthcare, and tech.

Select Customers

Also worked with Andrew Wilkinson and Brendan Bouchard (hosted agent-building events, acquired both as customers).

Experience

Head of Sales

Lindy (AI Agent Platform)

2023 – Present

Founding GTM hire and only GTM retained after company pivot. Personally acted as Lindy's first forward-deployed engineer while building and scaling the sales organization from zero. Grew the sales team from 1 to 4 reps in 3 months, owning hiring, onboarding, ramping, quota, and comp structures.

2025 Closed $3.4M in new ARR — 47% of total company revenue (company grew 650% YoY). Sold six-figure enterprise deals (Deltek, AppLovin, Socure, Prenetics) into CTOs, COOs, CROs, and CEOs across healthcare, tech, legal, and finance.
2024 Built healthcare vertical from zero to 500+ customers and $1M in revenue
GTM Abilities Deeply technical for a sales leader. Built ICP, pricing, discovery and demo playbooks, outbound motions, and MEDDPICC frameworks from scratch. Owned hiring, onboarding, ramping, pipeline management, and revenue strategy
Technical Scope Built and deployed 80+ autonomous AI agents. Multi-agent workflows, prompt design, evals, model evaluation (Anthropic, OpenAI, Gemini), API integrations, voice AI

Account Executive & Sales Lead

Teamflow

2022 – 2023

Averaged 160% to quarterly quota. Booked 50+ demos/month while leading SDR team, driving 200%+ outbound performance. Developed sales processes used in company's GTM pivot to Lindy.

Enterprise Account Executive

Cintas

2020 – 2022

130–160% to quarterly targets, closing $117K–$300K ACV deals with 5–10 year contract terms (total contract values up to $1.5M). Sold into COOs and Heads of Facility Services across education, government, healthcare, and tech — including Hai De Lao and St. John's Private School. Maintained $1M+ active pipeline.

Master Trainer, Sales and Mentor

Steve Nash Fitness World

2016 – 2020

Exceeded quota by 316% (year 1), 500% (year 2), and 580% (year 3). Designed and led a company-wide mentorship program for 12–15 trainers.

Skills

Technical

  • AI agent architecture
  • Prompt engineering
  • Multi-agent workflows
  • LLM evaluation and testing
  • Voice AI (ElevenLabs)
  • API integrations
  • Anthropic, OpenAI, Gemini
  • Cursor, Claude Code, Replit

Sales & GTM

  • Enterprise sales
  • MEDDICC, SANDLER, BANT
  • Challenger Sale
  • Selling With methodology
  • Solution engineering
  • 0 to 1 vertical building
  • ICP development
  • Pricing and packaging
  • Sales playbook creation
  • HubSpot

Projects

  • Advisory roles (stealth, seed, series A+)
  • Sales and career coaching
  • Interview coaching and mentorship

Influences

Principles to live by

  • Insist on the highest level of standards
  • Disagree and commit

Books

  • The Obstacle Is the Way — Ryan Holiday
  • Ego Is the Enemy — Ryan Holiday
  • The Hard Thing About Hard Things — Ben Horowitz
  • What You Do Is Who You Are — Ben Horowitz
  • To Sell Is Human — Daniel Pink
  • The Psychology of Money — Morgan Housel
  • Selling With

Recent obsessions

  • Coming soon

Community

Investor in AI fund TEDAI San Francisco (2024) Girls in Tech AI Hackathon Judge DevDay x MultiOn Judge Cerebral Valley Judge

Personal

Daily sauna, biohacking, cold plunge, pilates. Dog mom to Molly. Dreams of custom building a home. Bachelor superfan and obsessive podcast listener.

Find Common Ground

Hi! I'm here to help you find connections with Lindy. Share your LinkedIn or Twitter profile URL and I'll research and compare our profiles!

Let's connect

San Francisco, CA · 604-848-8619