The Role

We're hiring a Senior Outbound Sales Development Representative to own qualified pipeline for our upmarket sales motion. This is not a traditional, top-of-the-ladder SDR seat. You'll work inside an AI-powered outbound system that already surfaces warm, high-intent conversations from companies in our ICP - your job is to turn that interest into qualified meetings, move deals faster, and proactively work our highest-value accounts.

This is a senior individual-contributor role for someone who has done outbound before and does it well. We're looking for a self-directed operator who needs minimal hand-holding, brings real commercial judgment to every conversation, and helps raise the bar on how we sell - sharpening talk tracks, surfacing what's working, and setting the standard for the function as the team grows.

Who We're Looking For

We are NOT looking for:

X Reps who rely on spray-and-pray volume over meaningful pipeline

X Candidates who lean on scripts and can't hold a real, unscripted conversation

X People who measure themselves by activity rather than outcomes

X Reps who let warm or inbound leads sit without fast, sharp follow-up

We ARE looking for:
• A pipeline owner who takes full responsibility for converting interest into booked meetings
• Someone who sells in terms of problems, not features - and can run a genuine discovery conversation
• A confident phone operator who's comfortable handling skepticism and objections in real time, including reframing concerns about workforce analytics around trust, accountability, and outcomes
• A commercially aware operator who understands what actually makes deals move
• Someone who works alongside AI tools to move faster, not to replace the human conversation
• A coachable professional who takes feedback and implements it on the spot - seniority here means judgment and adaptability, not ego

What You'll Do

Pipeline Generation & Ownership Own the conversion of warm, AI-generated inbound and outbound responses into qualified meetings. Engage every lead quickly and move it forward with urgency, keeping a consistent flow of high-quality pipeline for Account Executives.

High-Impact Sales Outreach Run structured daily call blocks against high-signal accounts - engaged prospects, reactivated leads, existing customers, and closed-lost opportunities. Use the phone as your primary channel to accelerate conversations and qualification.

Lead Qualification & Conversion Quickly assess fit, identify buying intent, handle objections, and secure the meeting. Respond to replies with speed and relevance, and hold a high conversion rate from conversation to booked meeting.

Social Selling & Community Engagement Show up where target buyers are (LinkedIn, Reddit, and other relevant communities). Build credibility, add to the conversation, and surface opportunities that sit outside traditional sequences.

AI-Enabled Workflow Execution Lean on AI-driven systems that handle list building, segmentation, and initial outreach, so your time goes to the high-value human work - qualifying, converting, and advancing opportunities rather than manual prospecting.

Raising the Bar Bring your experience to bear on how we sell: feed back what's landing and what isn't, help refine talk tracks and objection handling, and model the standard for a growing outbound function.

Job Requirements

What we're looking for:

• 3+ years in an SDR, BDR, or outbound sales role, with a clear track record of consistently meeting or exceeding pipeline and activity targets
• B2B SaaS sales experience - you understand the buyer, the motion, and the sales cycle
• Strong phone presence and genuine comfort with high-volume, live calling
• Proven ability to run discovery and handle objections without a script
• Excellent written communication (email and social selling)
• Hands-on experience with CRM systems such as HubSpot
• Familiarity with tools like LinkedIn Sales Navigator
• Experience working with AI tools such as ChatGPT or Claude in your workflow
• Ability to operate effectively in a remote, async-first environment with high autonomy

Preferred:

• Experience selling into HR, IT, or Operations functions
• Background in workforce analytics or an adjacent SaaS category
• Experience with AI-assisted outbound or signal-based prospecting
• Exposure to upmarket or mid-market sales motions

Success in This Role

Success will be measured by:

• Conversion rate from positive reply to booked meeting
• Volume and quality of daily conversations across channels
• Meeting show rate
• Pipeline sourced for Account Executives
• Contribution to closed-won revenue

Why Join Us

• 100% remote and async-first - work from anywhere
• Mission-driven company shaping the future of work
• Strong product-market fit with tens of thousands of users and growing
• An AI-powered outbound engine that feeds you warm, high-intent conversations instead of cold lists
• Collaborative, humble, high-performing team
• Competitive base with strong on-target earnings, plus 30+ days of paid time off

Our Hiring Approach

• This is a full-time, 100% remote role, giving you the freedom to work from anywhere
• We hire globally, with flexible employment or contractor arrangements depending on location