Now hiring · 1099 inside sales · Remote · US-only

Join Outfitter.
Build a residual commission.

↑ COMPOUNDING RESIDUAL

Every customer you close pays you every month they stay. Your book compounds, month over month, for the life of the account. The closers who get in early build the biggest trail.

Outfitter is hiring its first inside sales reps to close small-business trade contractors onto the platform. Full-cycle closers only. AI voice agent (inbound + outbound) + email + SMS automation runs in your rep portal — your prospecting and inbound coverage are automated from day one.

Apply Now How it works

You close the deal.
The AI fills your pipeline.

This isn't a referral program. You're a real inside sales rep running full-cycle deals — discovery, demo, close — against small-business trade contractor owners. We hand you the leads and the AI to dial them; you take it from there.

1

Your portal loads pre-qualified leads

Pulled from our enriched 2.7M-contractor registry, filtered by trade, geo, and contact grade. Each lead comes with owner name, phone, website, and a score. Fresh lists every week.

2

Your AI voice agent works inbound + outbound

Outfitter's own voice agent — the product you're selling — runs against your list outbound, and answers every inbound call too so you never miss one. Email + SMS automation handles the follow-ups in parallel. It books callbacks, hands warm conversations to you live, and keeps the pipeline warm 24/7.

3

You demo. You close. You earn for life.

You run discovery + demo + close in a single week per typical deal. Commission compounds monthly from each customer's collected MRR — for as long as they stay on the platform.

Built for closers.

You run the process — discovery, demo, close. The AI runs the noise — dialing, follow-ups, callbacks, list pulls. You stay on the parts that close deals; the automation handles everything else so your pipeline never goes cold.

📇
Pre-loaded CRM
Enriched contractor leads pushed weekly into your pipeline by trade, geo, and contact grade. Owner name + phone + website + score, ready to dial.
🎙
AI voice + comms agent
Inbound + outbound voice running 24/7. Email and SMS automation handle the follow-ups. Warm conversations route to you live.
$$$
Live commissions tracker
Real-time book value. MRR earned this month. Lifetime trail accumulating. Projected payout if you close one more. You see the residual compound in real time.
🎯
Pitch + demo materials
Pre-built decks, demo videos, ROI calculators, and an answer book of common objections. Stop crafting your own collateral.

Experienced closers only.

This isn't an entry-level gig. It's also not for enterprise reps used to 6-month deal cycles. The sweet spot is a closer with 3+ years selling SaaS or services to small-business owners.

3+ years closing B2B SaaS or services to small-business owners. $100-$2K/mo deals. Phone + Zoom + email — the SMB motion.
You can run discovery → demo → close in under two weeks. Short cycles, owner-decision-maker conversations, no committee-based selling.
You'd rather earn more later than safer now. 1099 commission only. Your residual book compounds; the trade-off is no base.

Pitch us on you.

We respond to every legit application within 48 hours.

PDF only, 5 MB max. We read every one within 48 hours.

This is a 1099 independent contractor opportunity. Applying does not create any employment, contractor, or compensation relationship with OutfitterAI. Selected candidates sign a standard independent contractor agreement before any engagement begins.

OutfitterAI
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Your agent is ready. Ask anything about how Outfitter works for your trade.