Demo

Sales & Business Development Representative

PentaEye
Chicago, IL Full Time
POSTED ON 12/8/2025
AVAILABLE BEFORE 6/5/2026

About PentaEye

PentaEye is a fast-growing SaaS platform designed to help small and medium-sized businesses streamline daily operations—from attendance tracking and sales to inventory, training, scheduling, and more. Our mission is to empower business owners across the U.S. to manage multiple businesses effortlessly through a single, easy-to-use app.

We are expanding our U.S. sales team and seeking driven, competitive, relationship-oriented individuals who want to build a career with unlimited earning potential.



Overview

As a Sales & Business Development Representative, you will be responsible for growing PentaEye’s customer base, developing strong client relationships, and helping business owners discover how PentaEye can make their operations simpler and more efficient.

This role starts as commission-only, with incentives and milestone bonuses.

Once you achieve predefined targets (we can define the numbers later), you will move into a base pay commission model.

This is a high-growth opportunity for someone who wants to grow into Sales Lead, Growth Manager, or Regional Sales Manager roles.



What You’ll Do

Sales Strategy & Execution

  • Manage the complete sales cycle—from prospecting to closing deals.
  • Identify, research, and target ideal customer segments (retail, salons, daycare centers, restaurants, service businesses, etc.).
  • Perform outreach: cold calling, emailing, and follow-ups.
  • Present demos and product walkthroughs to business owners.

Client Engagement

  • Understand customer pain points and map how PentaEye solves them.
  • Build trust and long-term relationships with clients.
  • Assist new customers through signup, onboarding, and initial setup.

Market Understanding

  • Stay updated on small-business trends, operational challenges, and technology adoption in the U.S. market.
  • Provide feedback to leadership and product teams based on customer conversations.



Daily Responsibilities

  • Grow your pipeline through outbound calling and lead generation.
  • Manage your sales funnel using CRM tools.
  • Conduct virtual demos and product walkthroughs.
  • Assist new customers with setup and training.
  • Track progress, report metrics, and identify upselling opportunities.
  • Collaborate with marketing and support teams to improve conversions and retention.



Qualifications & Skills

Required

  • 0–5 years of sales, cold calling, telemarketing, or customer engagement experience.
  • Excellent communication and interpersonal skills.
  • Strong work ethic, self-motivated, and competitive mindset.
  • Ability to work independently and hit targets consistently.
  • Comfortable with CRM tools.

Preferred

  • Experience selling SaaS/technology products.
  • Experience working with small businesses in the U.S.
  • Understanding of business operations, service industries, or retail.



Compensation Structure

Phase 1: Commission-Only

  • Earn commission for every converted business.
  • Additional incentives for hitting weekly/monthly milestones.

Phase 2: Milestone-Based Base Pay

Once you reach a predefined target, you become eligible for:

  • Base salary commission
  • Performance bonuses
  • Opportunity to move into a full-time salary role



What We Offer

  • Uncapped commission structure.
  • Growth-based base salary after hitting milestones.
  • Opportunities for rapid promotion (Sales Lead → Regional Manager → Growth Manager).
  • Certificate recognition for milestone achievements.
  • Flexible working hours.
  • Remote-friendly U.S. work environment.



Who Should Apply?

This role is perfect for someone who:

  • Loves sales and thrives in performance-driven environments.
  • Is hungry, ambitious, and wants to grow.
  • Enjoys building relationships with business owners.
  • Wants independence and unlimited earning potential.
  • Wants to grow into leadership roles in sales or growth.


Salary.com Estimation for Sales & Business Development Representative in Chicago, IL
$83,517 to $111,700
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