Sales Lead | The “Promota" Gauntlet

DigiBuild Software; Chicago (IL); On-site; USD 50,000 - 80,000; Full time

Job summary

Promota.ai is looking for a Sales Lead to help build and close a scalable sales pipeline in an innovative role defining Autonomous Sales. Located in Chicago, the position offers a competitive compensation structure with base pay between $50k to $80k and commissions that can lead to total earnings over $250,000. Ideal candidates have a track record of rapidly closing deals and experience in high-pressure sales environments. Join an elite team of YCombinator alumni at the forefront of sales innovation.

Qualifications

• Experience scaling to $1M or $10M in sales with a startup.
• Proven ability to navigate through complex deals.
• Demonstrated success in converting inbound and outbound leads.

Responsibilities

• Convert high-intent inbound leads into sales.
• Refine outreach strategies for cold prospects.
• Participate in a multi-stage sales competition.

Skills

Sales conversion

Lead generation

Negotiation

Problem solving

Job description

Company: Promota.ai

Location: Remote / Chicago, IL

Compensation: $50k – $80k Base | $250,000 OTE (Uncapped)

Format: Multi-Stage Performance Trial

The Mission

Promota.ai is defining the Autonomous Sales category. We build autonomous digital workers that replace traditional SDR functions: researching, prospecting, managing omnichannel ads and outbound to make sales 24/7.

We recently closed a $1.2M Pre-Seed round with premier VCs from San Francisco, Chicago, and Miami. We are lean, high-leverage, and scaling rapidly. We don’t want account managers—we want Closers.

The Role: High-Velocity Conversion

We provide the engine, you finish the sale. As a Sales Lead, you will help build out our scalable sales pipeline while also working to close a large pipeline of warm leads.

• The Warm Pipeline: We have a consistent stream of high-intent inbound leads from our founder network and autonomous outbound engines. Your primary goal is to convert as many of these as possible.
• The Cold Hunt: You will partner with our digital agents to penetrate new customers. You will refine the Agent's outreach strategies and step in to bridge the gap between a digital handshake and a signed contract.

The Transparent Hiring Process: 'The Gauntlet'

We value your time and we move with speed. We use a 3-part transparent process to find the best:

• The Sales Competition (The Gauntlet): We hire 3 candidates for a paid, 2-week iteration cycle. You will be given a mix of warm inbound leads and cold outreach resources. We want to see how you convert under pressure and problem solve. We hire fast and fire fast—the top performers move forward, this could be 0, 1, or 2, it is purely results based.
• Team Member Interview: A deep dive with our engineering and ops leads to ensure you understand the "Autonomous Sales Seat" product you are selling.
• Cofounder Interview: A final strategy session with the founders to discuss strategy, equity, and long-term vision.

Who You Are

• The Scaler: Ideally, you have helped a YC or VC-backed startup scale to $1M or $10M in sales.
• The Ex-Founder: You’ve built something from nothing and isn’t afraid of a No. You just get things done.
• The Mercenary: You hate fluff. You want to spend 100% of your time on the hunt and the close.
• The Professional: You can navigate unsexy industries with the same sophistication as a corporate boardroom.

Why Join Us?

• Elite Pedigree: We are alumni of YCombinator, Google, Microsoft, and BloomTech, cofounders are influencers, and we’re backed by respected VCs.
• Category Creators: We are a top early-stage company in the autonomous sales space. You aren't selling a tool, you are offering the future of sales—the “Autonomous Seat”.
• Uncapped Upside: A compensation structure designed for top performers to clear $250,000+ through aggressive, uncapped commissions.

Are you ready to run the gauntlet?

Apply with your LinkedIn and a brief summary of the most complex deal you’ve closed in under 30 days.