The Role
Lead and build Littlebird's outbound sales function: create pipeline, convert self-serve users to customers, run full sales cycles, onboard and enable customers, feed product feedback, automate processes using Littlebird, and build the repeatable enterprise sales playbook.
Summary Generated by Built In
About the role
What you’ll do
What you bring
Why join Littlebird?
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)
Skills Required
- Experience in enterprise B2B SaaS sales (BDR/SDR background through quota-carrying roles)
- Proven track record of meeting and overdelivering on sales quotas
- Full-cycle sales experience: sourcing, demos, procurement, pricing, closing, and expansion
- Experience building or leading a sales function or team
- Ability to build outbound motion: list building, sequencing, outreach, and measurement
- Strong operational and automation mindset; comfortable using and optimizing sales tools and AI
- Customer onboarding and enablement experience to drive customer value and expansion
- Comfort working in a fast, scrappy startup environment with high ownership
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The Company
What We Do
Littlebird is the full-context AI assistant for Mac—a personal AI that continuously understands your screen and meetings to deliver answers grounded in what you're actually working on. Founded by Alexander Green, Alap Shah, and Naman Shah, the company is based in San Francisco. Available now at littlebird.ai.
