---
title: 'Founding Sales Leader at Littlebird'
canonical: 'https://feeny.ai/job/founding-sales-leader-littlebird-san-francisco-8asr2hrz3cpx'
type: 'job'
last_seen: '2026-09-09'
---

# Founding Sales Leader at Littlebird

- **Company:** Littlebird
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-07-28
- **Last confirmed live:** 2026-09-09
- **Apply:** https://jobs.gem.com/littlebird/am9icG9zdDogr_NEAQjnaWD5NraIdUrP

## Job description

## About the role

Littlebird is growing fast and the people who try it tend to tell everyone they know. That's given us organic traction inside companies of every size, from solo founders to teams at major enterprises. But word of mouth alone won't get us where we're going. We need someone who can build the outbound engine to reach the companies we're not in yet, turn the interest we already have into real commercial relationships, and help shape what the enterprise version of Littlebird becomes.

Right now the GTM motion runs on founder time. It's time for our first dedicated sales hire to own the whole thing end to end and build the function from scratch.

## What you’ll do

- Build the outbound engine. Set up the systems and infrastructure to create pipeline that doesn't exist yet: list building, sequencing, outreach, targeting, and the tooling to measure what works. You're creating net new opportunities from scratch.
- Turn signal into pipeline. We have users inside companies we've never spoken to. Work that organic interest, turn self-serve signups into conversations, and conversations into deals. No warm account left cold.
- Run the full deal cycle. Demos, pricing, negotiation, and close. You own each account from first touch through expansion. The single point of ownership for everything commercial.
- Get customers to value. Own onboarding, live trainings, and use-case-specific enablement so new customers succeed fast and expand.
- Shape the enterprise product. You'll be on the front lines with customers every day, which means you'll see patterns and gaps before anyone else. We expect you to feed that back into product in tight loops and help define what the enterprise version of Littlebird becomes.
- Automate the motion with Littlebird. You'll be using our own product to run your sales process: meeting prep, follow-ups, CRM hygiene, research on accounts, drafting outreach in the right voice. You should be the kind of person who looks at a repetitive task and immediately thinks "I can automate this." Dogfooding isn't a side benefit here, it's core to how we work and how we'll learn what to build.
- Build the playbook. You're first, so you'll define the motion: what converts, what scales, what to automate, and what the next GTM hires should do.

## What you bring

- You've grown up in enterprise B2B SaaS sales. You probably started as a BDR or SDR, worked your way up to carrying a quota as a rep, and at some point led or built a team. You've lived through every stage of the machine and you understand how the pieces fit together because you've been the one running them.
- You've carried a quota and beaten it. Not just hit it, overdelivered. You know what it feels like to own a number and you're hungry to do it again, this time with full ownership of the motion, not just one piece of it.
- You're a full-cycle operator. Sourcing, demos, procurement, pricing, close, expansion. You've run deals end to end and you're comfortable owning every stage.
- You're a builder at heart. You're energized by the scrappy 0-1 phase more than just executing a polished playbook someone else wrote. You create pipeline and process from scratch, and you know the unglamorous side of being at a startup is sometimes the most important.
- You move fast and you're highly accountable. You find the work, own the outcome, and don't wait for permission. You're comfortable making calls with incomplete information and adjusting as you go.
- You're technically curious and tool-native. You don't need to code, but you should be the kind of person who lives in tools, hacks together workflows, and gets genuinely excited about using AI to do your job better. You'll be using Littlebird every day to sell Littlebird, and your feedback will directly shape what we build.

Why join Littlebird?

Littlebird is building a personal AI that connects your entire digital life, protecting your focus from clutter and surfacing what you need, the moment you need it. As the lead on Social, you will define how the world sees us.

We're a small, distributed team that works quickly, communicates clearly, and values people who take initiative. You’ll have a lot of ownership in this role, along with the support and resources you need to do great work.

- A fully remote work environment
- Competitive salary + meaningful equity in an early-stage company
- Comprehensive health benefits (medical, dental, vision)
- Unlimited PTO
- 401(k) plan available
- A team that cares about craft, clarity, and doing good work
- Locations: San Francisco, New York, Remote (US)

## About Littlebird

## Company Overview
- **One-liner**: Littlebird is a full-context AI assistant for macOS that continuously observes your screen and meetings to deliver answers and automate tasks based on your actual work context.
- **Entity Type**: Private (Seed stage – $11M raised)
- **Headquarters**: San Francisco, California, United States
- **Founded**: 2024
- **Founders**: Alap Shah, Alexander Green, Naman Shah

## Core Business
- **Primary industry/industries**: AI-powered productivity / Context-aware AI assistants
- **Target customers**: Individual professionals, knowledge workers, and teams using macOS (B2C, also potentially B2B via enterprise-grade security)
- **Mission or purpose statement**: (From website) “Organize your life and work… an AI that knows and understands what you're working on, so you can stay focused on what matters.”

## Products & Services
- **Littlebird (macOS App)**: A desktop AI assistant that runs in the background, reading the active window on your screen and transcribing meetings to build a private memory of your work. No manual setup or copy/pasting required. It can answer questions, draft emails/docs in your voice, take meeting notes, and automate daily routines (e.g., morning briefings, weekly summaries). Available for Apple Silicon, macOS 13+. Companion apps for iOS and Android allow querying on the go.
- **Paid Plans**: Free tier with limited usage; paid plans starting at $20/month for higher limits and features like image generation.
- **Integrations**: Optional integrations with hundreds of tools across categories: project management (Notion, Linear), design (Canva, Miro), developer tools (Cloudflare, PlanetScale), CRM (Intercom, Outreach), finance (Mercury, Ramp), meetings (Calendly, Granola), marketing (Klaviyo), analytics (Mixpanel), knowledge (Guru, Google Drive), email/calendar (Gmail, Outlook, Apple Calendar). Integrations are optional; the core product works by observing the screen.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (private company)
- **Key Metric**: Total funding $11M (Seed round, March 2026)
- **Notable Investors/Partners**: Led by Lotus Studio; participants include Lenny Rachitsky, Scott Belsky, Gokul Rajaram, Justin Rosenstein, Shawn Wang, and Russ Heddleston.
- **Growth Signals**: LinkedIn reports 30 employees (+1600% YoY) as of early 2026; offices in San Francisco and Newark; distributed across 7 countries (India, US, Poland, Pakistan, Ukraine). 84% of users say it saves at least half a day per week (per company claim). Rapid LinkedIn follower growth (+5122% yearly).

## Competitive Advantages
- **Full-context memory without setup**: Unlike general AI assistants that require manual copying/pasting, Littlebird automatically understands the current project, document, and conversation by reading the screen. This makes responses faster and more personalized.
- **Native macOS background operation**: Works on Apple Silicon with minimal friction, observing the active window and running meeting transcription via system audio.
- **Privacy-first design**: Users control what is seen/kept; data encrypted at rest and in transit (AWS); SOC 2 certified, GDPR and CCPA compliant. No data sold or used to train models.
- **Proven founding team**: Co-founders previously sold Sentieo (AI platform for investors) to AlphaSense; also built health-food company Thistle. One co-author of the “Citrini” paper that impacted tech stocks.

## Strategic Focus
- **Scaling the user base**: Currently free to download with a paid subscription model to drive adoption among knowledge workers.
- **Expanding platform support**: Already available on Mac, Windows (likely in beta or announced), plus mobile companion apps.
- **Deepening integrations**: The product relies on optional app connections to provide deeper context; likely expanding integration library and automation capabilities (Routines feature).
- **Enterprise adoption**: Emphasis on security compliance (SOC 2, GDPR) suggests a push into B2B sales and team/enterprise plans.

## Why Work Here
- **High-growth startup**: 30 employees, huge YoY headcount increase, well-funded seed round. Opportunity to shape product and culture early.
- **Hybrid Work Policy**: “Hybrid Workspace” as per Built In – employees combine remote and on-site work, with typical time on-site mentioned (likely SF office).
- **Culture & Perks**: No specific perks listed, but emphasis on privacy, automation, and building for power users. Founder background in multiple successful startups indicates a fast-moving, engineering-centric environment.
- **Current Openings** (as of mid-2026): Product Analyst, Senior Social Media Manager, Senior Backend Engineer, Social Media & GTM Intern, Product Manager – suggesting both engineering and go-to-market teams growing.

## Sources
1. [littlebird.ai/about-us](https://littlebird.ai/about-us)
2. [builtin.com/company/littlebird-ai](https://builtin.com/company/littlebird-ai)
3. [littlebird.ai](https://littlebird.ai)
4. [linkedin.com/company/littlebirdai](https://linkedin.com/company/littlebirdai)
5. [techcrunch.com](https://techcrunch.com/2026/03/23/littlebird-raises-11m-to-capture-context-from-your-computer-so-you-can-query-your-data)

## Other roles at Littlebird

- [Creator in Residence](https://feeny.ai/job/creator-in-residence-littlebird-remote-6cctbk4demjb)
- [Product Manager](https://feeny.ai/job/product-manager-littlebird-bengaluru-h9ev0j3s8dbm) — Bengaluru, India
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- [Senior Backend Engineer](https://feeny.ai/job/senior-backend-engineer-littlebird-remote-ajgp4w2p8bns)
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