Sales Development Representative

Freedom; New York (NY); On-site; USD 60,000 - 90,000; Full time

Benefits offered by this job

Health insurance

Unlimited PTO

Job summary

Freedom, an AI-native payroll and benefits platform, is hiring an SDR in New York City to lead outbound prospecting and generate qualified meetings with startup founders and SMB owners. You will craft target lists, research accounts, and test new channels to build a repeatable outbound motion.

You will work directly with the CEO to shape the playbook and scale the team as it grows. Strong performers can advance to AE or growth roles as the team expands, with ownership from day one and a path

Qualifications

• 1+ year in a demanding role (sales, banking, consulting, teaching, or running your own thing).
• Fast learner who can teach themselves new skills.
• Clear, sharp communication in writing, on the phone, and over video.
• Comfort talking to founders as a peer.
• Thrives with ambiguity and takes initiative.

Responsibilities

• Generate qualified meetings with startup founders and SMB owners entirely through outbound prospecting.
• Build your own target lists and research accounts before outreach.
• Write, test, and iterate on cold outreach across email, LinkedIn, phone, and new channels.
• Identify patterns in conversions and document them into ICP and playbooks.
• Learn payroll and benefits well enough to have credible conversations with founders, finance leads, and operators.
• Log touchpoints and keep the pipeline clean.
• Provide feedback from prospects to product and founders.
• Build scalable systems to grow from one SDR to many.

Skills

Communication

Fast learner

Ambiguity tolerance

Proactive

Founder conversations

Job description

Sales Development Representative (SDR)

New York City · In office [5x/week] · Full-time

About Freedom

Freedom is the AI-native payroll and benefits platform for startups and small businesses. Payroll, benefits, tax registration, and compliance are built from scratch with AI at the core. Our model is simple: payroll is free. Incumbents charge per employee per month for software that's slow, opaque, and run by large ops teams. We give founders great payroll for $0. We launched quietly, and the company is spreading quickly through word of mouth. Now we're building the go-to-market engine.

About the Role

You'll be one of the earliest hires, and it's an entrepreneurial role where you'll have lots of responsibility and opportunity on day one. The role is outbound, and new meetings will come from prospects you found and reached first. There's also no playbook, and no sequence library. You'll work directly with our CEO to figure out the outbound motion. Then you'll turn what works into a repeatable system that future reps will run.

This role is for someone who wants to build something, not slot into something that already exists. If you're looking for established processes and a well-worn path, this isn't the right fit yet. If you want the path to be the one you built, it is.

Strong performers will have a clear path to AE, or other growth roles as the team scales.

What You'll Do

• Generate qualified meetings with startup founders and SMB owners entirely through outbound prospecting
• Build your own target lists and research accounts before you reach out
• Write, test, and iterate on cold outreach across email, LinkedIn, phone, and channels nobody's tried yet
• Find the patterns in who converts and document them into our ICP and playbook
• Learn payroll and benefits well enough to have credible conversations with founders, finance leads, and operators
• Log touchpoints and keep the pipeline clean
• Feed what you hear from prospects back to product and the founders
• Build the systems that let us scale from one SDR to many

What You Need

We don't care where you went to school or what you majored in. We care how driven you are to win here.

• 1+ year of excellence in a demanding role, such as sales, banking, consulting, teaching, customer success, or running your own thing
• A track record of learning fast and teaching yourself new skills
• Clear, sharp communication in writing, on the phone, and over video
• Comfort talking to founders as a peer
• Real comfort with ambiguity: you'd rather define the process than wait for one
• High urgency and a bias toward action

Who Thrives Here

• Former athletes who miss competing
• People have'd built something from nothing
• Founders who did their own sales
• People who treat rejection as data, not defeat

Most Important Qualities

• Figure-it-out factor: You see a blank page as an opportunity.
• Competitive drive: You keep score and hate losing.
• Coachability: You ask for feedback and act on it the same day.

Nice to Haves

• Startup experience, especially early-stage
• Network in the startup or tech community
• Experience with outbound prospecting tools
• Familiarity with payroll, HR, benefits, or fintech

Compensation & Benefits

• Health, dental, vision
• Unlimited PTO