Executive Coaching In Jobs in Chicago, IL (NOW HIRING)

Sales Associate – Hybrid

+$85K OTE, Base $40,000 + Uncapped Commission + Bonuses | Rapid Career Growth | High‐Trust Culture

City Wide Facility Solutions - Chicago Southland & Northwest Indiana is hiring a Sales Associate or Junior Sales Executive who loves hunting, talking to people on the phone, and building pipeline. This is a structured, high‐activity role for someone who wants a clear, paid path into a six‐figure Sales Executive position.

Requirements - The Opportunity

First 12 to 18 Months:

• • Make 50+ outbound calls/day and 25+ follow‐ups/day to targeted commercial accounts.
  • Run multi‐touch cadences (phone, email, LinkedIn) and work defined prospect lists - not random dialing.
  • Identify decision‐makers, uncover real facility and janitorial needs, and book high‐value, sales‐ready appointments.
  • Partner closely with a senior Sales Executive, who will run discovery, proposals, and closing from the meetings you create.

Hybrid schedule: 3 days/week in our Frankfort, IL office, 2 days/week from home for focused calling and follow‐up.

How You’ll Be Paid / Compensation & OTE:

• • Base salary: $40,000. Designed to attract sharp early‐career talent while keeping the real upside in performance.
  • Weekly Activity Bonus – $/week: Paid only when you hit all of the following:
  • • 250+ outbound dials/week
    • 250+ follow‐up touches/week
    • Clean, accurate CRM entries (no fake activity)
    • Proper cadence use and progress through target lists
    • • If the activity isn’t real, there’s no weekly bonus.
  • • Earnings are directly linked to impactful new revenue, not just activity.
  • Qualified Appointment Bonus – $ per meeting: Paid only for high‐quality, sales‐ready appointments that meet these criteria:
  • • Confirmed decision‐maker attends
    • Clear need or interest identified
    • Expected contract value >$/month
    • Senior Sales Executive accepts it as “sales‐ready”
  • Closed-Won Commission – Paid on New Recurring Revenue
  • • Eligible to earn commissions in accordance with the Company's Sales Commission Plan.
    • Commissions are based on the profitability (gross margin) of new recurring accounts you source and close.
    • Commission is earned after the client's first paid invoice is received, in accordance with the Company's commission policy.
    • Higher-value, higher-margin, longer-retained clients create greater long-term earning opportunities.
  • Promotion Path: At month 13, you’re reviewed for promotion based on:
  • • 6 consecutive months of hitting activity and appointment quotas
    • Average 3+ closed‐won accounts per month sourced from your meetings
    • Strong qualified‐meeting ratio and reliable show rates
    • Hit the standards and you graduate to Sales Executive with $100K+ OTE, a larger base, and full‐cycle responsibility.

How You’ll Work:

• • • Hybrid schedule: 3 days a week in our Frankfort, IL office; 2 days remote.
    • In‐office: power hours of outbound calls, coaching, and collaboration with senior Sales Executives.
    • Remote: focused prospecting blocks, multi‐touch follow‐up sequences (aiming for 8+ touches per prospect), and pipeline organization in CRM.

What You Bring:

• • • Recent grad or early‐career B2B rep / call‐center / collections pro comfortable living on the phone and in email.
    • Competitive, resilient, coachable, and organized in CRM.
    • Enjoys a high‐activity, low‐drama environment where the job is simple: talk to business men and women, set great meetings, and get paid when those meetings turn into contracts.
    • Minimum 2 years of B2B sales or SDR/BDR experience with a track record of hitting or beating activity and pipeline goals.
    • Comfortable making 50+ new outbound calls per day, handling rejection, and staying disciplined.
    • Strong phone and email communication skills, CRM discipline, and a competitive, coachable mindset.
    • Competitive “athletic” mindset - self‐motivated team players who hate losing more than they love winning.
    • Tech‐savvy and organized with experience using MS Dynamics 365, or other CRM and digital sales tools.
    • Energetic, coach‐ready, and driven to build a six‐figure career through honesty, consistency, and execution.

If you want a straightforward, numbers‐driven way to prove yourself and grow into a high‐earning B2B sales career, this Junior Sales Executive Hunter Track is built for you.

Benefits

What's In It For You?

• $40,000 base salary + unlimited commission and desired performance (we want you to earn from commissions and performance bonusses (earnings examples shared during interviews)).
• Merit-based Growth and leadership Opportunities in a target rich environment
• A trusted, supportive environment that values honesty and self‐management.
• Exceptional training, mentorship, and a defined career path toward leadership or senior sales roles.
• A balanced hybrid work schedule, structure for year‐round productivity and well‐being.
• Comprehensive benefits, Industry Leading Sales Training and LMS,
• Company assigned iPhone & other devices

If You’re Ready To Build - Not Just Sell

f you’re ready to prove you can create revenue, not just talk about it - and get paid accordingly - this Junior Sales Executive Hunter Track is your next move.

If you are think you this is the team for you, then apply and we will see. Otherwise, thanks for reading and good luck to you!

City Wide Chicago Shores territory is a dynamic territory serving the thriving Chicago Southland and Northwest Indiana region - a target-rich environment packed with commercial properties, businesses, and facilities along the Lake Michigan shoreline. As North America's leading management company in building maintenance, we simplify operations for clients by providing one point of contact for janitorial, commercial cleaning, lawn care & landscaping, snow removal services, disinfecting, floor care, handyman services, parking lot repairs, sealcoating & striping, and 20+ additional customized facility solutions, allowing property managers and owners to save time, reduce vendor headaches, and focus on their core business while we deliver reliable, high-quality results.