[Hiring] Sales Development Representative @Worksome

Role Description

Worksome is the FEMS (Freelance and External Workforce Management System) category leader. Everest Group named us a Leader in its PEAK Matrix for two consecutive years. We're growing 60%+ a year, just hit profitability, and 350+ enterprises run their external workforce on us, including major brand names across Creative Agencies, Pharma, and Consulting. The category is finally waking up, the analyst tailwind is at our back, and we're now scaling the US even further.

You'll be the first SDR on the ground in North America. Not the tenth, not the third. The first. That means you book meetings on day one, and by month six you've helped build the function.

What you'll actually do:

• Hunt: Work with named accounts in various industries (typically fast-moving, digitally driven industries) across functions such as HR, Procurement, and Talent Acquisition at enterprises with serious contingent workforce spend. Run high-volume outbound and close the loop on every signal that comes in. If a list of 200 accounts lands on your desk on Monday, you don't ask for a playbook. You build one and book meetings by Friday.
• Build: Work directly with the CEO, CMO, and SVP Sales to design the SDR motion from scratch. Sequences, ICP refinement, qualification frameworks, AE handoff, the comp plan you'll eventually hire other SDRs onto. No 50-page corporate playbook to follow.
• Automate: Use Apollo, HubSpot, n8n, Claude, and other tools across our GTM stack. Push them harder than we do and build your own workflows in sync with Marketing and Sales. Automate list enrichment, signal scoring, and first-touch personalization with AI.

Qualifications

• At least two years of enterprise SaaS outbound experience with proven outcomes (quota attainment, meetings booked, pipeline sourced, conversion rates).
• Experience selling into HR, Procurement, or Talent at the enterprise level is a strong plus.
• Experience in related industries such as EoR, Payroll, HR tech, or similar is advantageous.
• Comfortable working in a remote role with discipline and savvy in communication styles and toolstack.
• AI native with experience building agents, running sequences in n8n or Make, and using Claude or ChatGPT for drafting, research, and qualification.
• A desire to be the first, not the next, with a vision for a long-term career trajectory.
• Frank, low-ego, and high-agency attitude.

Requirements

• Ability to show what you've built in terms of AI workflows for prospecting.
• Willingness to go the extra mile to run the function within 18 months.

Benefits

• Base salary of $65K, $85K OTE, uncapped, with accelerators kicking in above 100%.
• Warrants and full benefits.
• Direct path to Head of SDR North America as we scale, AND/OR into AE or sales leadership.
• Daily mentorship from our VP Sales (ex-Workday, ex-SAP) and the Marketing leadership, including a co-founder.
• Opportunity to say you were the first SDR at the FEMS category leader during a pivotal moment in the industry.

How to apply

Send a resume and a short note (a paragraph, not a cover letter) telling us:

• The numbers from your last SDR role: quota, attainment, meetings, pipeline.
• The most useful AI workflow you've built for your own prospecting, and what it did for your output.
• Why founding SDR at Worksome, specifically.

Point 2 is a showstopper. We look forward to hearing from you.