Founding Sales Leader

Littlebird; San Francisco, New York (CA, NY); Hybrid; USD 180,000 - 260,000; Full time

Benefits offered by this job

Fully remote work environment

Competitive salary

Meaningful equity

Health benefits

Unlimited PTO

401(k) plan

Job summary

Littlebird is hiring its first dedicated sales hire to own the full GTM motion from outbound to close. You will build the outbound engine, nurture signals into conversations, and own the entire deal cycle, onboarding, and post-sale expansion.

You will shape the enterprise product through close customer feedback and create scalable processes with AI-driven automation. We are a fully remote team with a competitive salary and meaningful equity.

Qualifications

• Experience selling enterprise B2B SaaS to mid-market and large organizations.
• Proven track record of meeting or exceeding quota across full sales cycle.
• Able to build and own outbound motion from scratch in a fast-growing startup.
• Comfort with 0-1 phase: create processes and tooling to scale.

Responsibilities

• Build outbound engine: lists, sequencing, outreach, and tooling to create new pipeline.
• Turn inbound signals into conversations and deals; convert signups to customers.
• Own the full deal cycle: demos, pricing, negotiation, closing, and expansion.
• Own onboarding and enablement to drive time-to-value for new customers.
• Provide feedback to product on enterprise needs and help shape the product roadmap.
• Automate repetitive sales tasks using Littlebird and other tools to improve efficiency.
• Define the GTM playbook for the first dedicated sales hire and beyond.

Skills

Enterprise B2B SaaS

Quota ownership

Full-cycle sales

Startup builder

Automation mindset

Job description

View all jobs Founding Sales Leader San Francisco New York Remote GTM Remote Full-time

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)