Top 393 Head of sales Jobs in Chicago Il

Director of Field Sales: Tesla Energy, Roofing & Home Improvement
Phoenix Exteriors & Restorations —Chicago, IL
- $125,000 - $350,000 a year
- Full-time
- Management
- Residential
- Driver's License
- Health insurance
- Dental insurance
Quick Apply
10d
Senior Director, Partner Sales
Braze —Chicago, IL
- $132,000 - $330,000 a year
- Senior level
- Commercial
- Paid parental leave
- Health insurance
Quick Apply
Director of Sales & Marketing, Independent Senior Living
Chestnut Square at The Glen —Glenview, IL
- From $82,000 a year
- Weekends as needed
- Sales
- 3 years
- Bachelor's degree
- 403(b) matching
- Health insurance
Quick Apply
Director Area Independent Living Sales
Lifespace Communities —Chicago, IL
- $132,200 - $190,300 a year
- Full-time
- Marketing
- Office
- 8 years
Quick Apply
Head of Sales, Central
Nextdoor —Chicago, IL
- $192,000 - $240,000 a year
- 6 years
- Analysis skills
- Recruiting
- Health insurance
- Work from home
Quick Apply
Founding Head of Enterprise Sales
Creative Market —Chicago, IL
- $200,000 - $300,000 a year
- Full-time
- Remote
- Business development
- Military encouraged
- Senior level
- Health insurance
- Dental insurance
Quick Apply
Regional VP of Sales – Power Distribution
Siemens —Chicago, IL
- $188,282 - $322,769 a year
- Full-time
- Hybrid work
- Up to 50% travel
- Bachelor's degree
- Travel
Head of SMB Sales, Grocery & Retail (US&C)
Uber —Chicago, IL
- $130,000 - $228,571 a year
- Full-time
- Hybrid work
- Office
- Recruiting
- Contracts
Head of Sales Strategy - Grocery
Uber —Chicago, IL
- $236,667 - $291,667 a year
- Full-time
- Office
- SQL
- Project management
Head of Industry, Retail, Large Customer Sales
Google —Chicago, IL
- $201,000 - $281,000 a year
- Full-time
- Customer service
- 3 years
- Bachelor's degree
12d
National Sales Director (East)
SmartRent —Chicago, IL
- $220,000 - $270,000 a year
- Remote
- Presentation skills
- Travel
- Contracts
- Paid parental leave
- Employee stock purchase plan
Quick Apply
SVP, Client Sales & Insights - Mid-Market National Team Lead - (Remote, Chicago preferred)
Circana —Chicago, IL
- $300,000 - $330,000 a year
- Remote
- Background check
- Merchandising
- Mid-level
- Health insurance
- Dental insurance
Quick Apply
2d
Director of Sales Training - High Ticket
Curvion Blue —Chicago, IL
- $120,000 - $150,000 a year
- Full-time
- Remote
- Senior level
- Teaching
- Analytics
Quick Apply
Senior Director, Head of Convenience Retail & On-Premise Sales
fairlife —Chicago, IL
- $195,000 - $215,000 a year
- 5 years
- Bachelor's degree
- Travel
- Paid parental leave
- Health savings account
Quick Apply
12d
Director, Grocery Sales-Central
Kinder's —Chicago, IL
- $215,000 - $240,000 a year
- Remote
- Merchandising
- 11+ years
- Bachelor's degree
- Health insurance
- 401(k)
Quick Apply
Head Of Sales
AIDS Healthcare Foundation —Chicago, IL
- $18 an hour
- Senior level
- Paid parental leave
- AD&D insurance
Quick Apply
Sales Director, Product Specialists (Smart Trailers)
Samsara —Chicago, IL
- $420,000 a year
- Public speaking
- 3 years
- Senior level
- Health insurance
- Parental leave
High Ticket Sales Director
Curvion Blue —Chicago, IL
- $120,000 - $360,000 a year
- Full-time
- Remote
- Continuous improvement
- Recruiting
- Senior level
Quick Apply
Director of Sales & Marketing - Hotel 55 Chicago
Coury Hospitality —Chicago, IL
- $150,000 - $160,000 a year
- Full-time
- Hotel
- Analysis skills
- Senior level
Quick Apply
Executive Director Head of Americas Retail Sales and Distribution
CME Group —Chicago, IL
- $215,300 - $358,900 a year
- Full-time
- Google Workspace
- Travel
- Conflict management
- Health insurance
- 401(k)

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Director of Field Sales: Tesla Energy, Roofing & Home Improvement

Phoenix Exteriors & Restorations -
Chicago, IL

Quick Apply

Job Details

Full-time
$125,000 - $350,000 a year
10 days ago

Benefits

Health insurance
Dental insurance
401(k)
Paid time off
Vision insurance
Life insurance

Qualifications

Energy sales
Renewable energy
Team development
Hiring
Driver's License
Recruiting

Full Job Description

https://careers.hirebus.com/jobs/f3323c4e-f75a-4c4d-b8e5-e375caab40fa

Director of Field Sales: Tesla Energy, Roofing & Home Improvement

Phoenix Exteriors | Chicagoland, IL
Base Salary: $125,000–$150,000
Total Compensation: $250,000–$350,000+ OTE based on team production

Phoenix Exteriors is hiring a proven Director of Field Sales to build and lead our roofing, storm restoration, solar, Tesla Energy, and home improvement sales organization across Chicagoland.

This is not a desk-manager role. This is a field leadership role for someone who has already built, recruited, trained, and managed outside sales teams that produce.

Phoenix Exteriors is one of the most unique companies in the Midwest home improvement market. We are a leading Tesla Solar Roof installer for Chicagoland, with a growing Tesla Energy relationship in Tennessee. Our platform combines storm restoration, premium roofing, Tesla Solar Roof, Tesla Solar Panels, Tesla Powerwall 3, Tesla Wall Connector, SPAN smart panels, siding, windows, gutters, and high-end exterior upgrades.

Our growth model is simple:

Storm-damaged roof opportunity → homeowner inspection → insurance claim support → premium roof replacement → Tesla Energy upgrade → additional exterior home improvement sales.

We are looking for a sales leader who can turn that model into a repeatable field sales machine.

As this role becomes successful in the Chicagoland market, Phoenix Exteriors intends to expand this sales model into Nashville, Tennessee and Memphis, Tennessee, building localized canvassing, closing, and production centers around the same roofing, storm restoration, and Tesla Energy platform.

This Role Is For You If

You have already built or managed a door-to-door canvassing team.
You have led closers selling high-ticket home improvement, roofing, solar, windows, siding, HVAC, pest control, alarms, or another in-home sales product.
You know how to recruit, train, ride along, inspect activity, manage CRM discipline, and hold reps accountable.
You are comfortable leading from the field, not just from a conference room.
You understand that great sales leadership means building people, building process, and building production.
You can prove your past results with real numbers: team size, revenue, close rates, appointment set rates, inspection rates, show rates, and average ticket size.
You are open to travel as the model expands beyond Chicagoland, especially into Nashville and Memphis.

Do Not Apply Unless You Can Show

A proven record managing outside sales reps, canvassers, setters, or closers.
Experience building or scaling a D2D, canvassing, storm, solar, roofing, remodeling, or in-home sales team.
A history of recruiting, onboarding, coaching, and retaining salespeople.
Real CRM discipline and the ability to manage activity, pipeline, follow-up, and production.
The ability to ride with reps, coach at the door, inspect sales calls, and train closers in the field.
The ability to build both lead generation and closing systems.

What You Will Build

A door-to-door canvassing and storm-response lead generation team.
A structured setter-to-closer sales process.
A recruiting, onboarding, and training program for new reps.
A field coaching system with ride-alongs, door coaching, sales call reviews, and weekly scorecards.
A CRM-driven sales process where no lead, inspection, claim, proposal, or follow-up falls through the cracks.
A repeatable sales model that converts roofing opportunities into solar, Tesla Energy products, Powerwall, SPAN, siding, windows, and premium exterior upgrades.
A scalable field sales model that can be duplicated in Chicagoland, Nashville, and Memphis.

What You Will Lead

Outside sales representatives.
Canvassers and door-to-door lead generators.
Roofing and storm restoration closers.
Solar and Tesla Energy closers.
Field sales meetings, trainings, ride-alongs, and performance reviews.
Neighborhood campaigns after hail and wind events.
Daily and weekly sales accountability.
Future field sales expansion into Tennessee markets.

Why Phoenix Exteriors

Phoenix Exteriors has been serving homeowners for nearly 20 years.
We are a leading Tesla Solar Roof installer in Chicagoland and have a growing Tesla Energy relationship in Tennessee.
We are one of the rare roofing-led companies in our market with the roofing experience, solar expertise, electrical capacity, and long-running trusted industry veteran relationships needed to deliver roofing, solar, battery, and smart panel projects under one coordinated platform.
Most roofing companies must hand solar and electrical work off to outside EPCs or disconnected subcontractors. Phoenix Exteriors is built differently. We understand the roof, the electrical system, the solar system, the battery, the homeowner, the insurance claim, and the complete exterior upgrade opportunity.
We sell premium roofing systems, Tesla Solar Roof, Tesla Solar Panels, Tesla Powerwall 3, Tesla Wall Connector, SPAN smart panels, siding, gutters, windows, DaVinci, standing seam metal, slate, and other high-end exterior products.
We were recognized with REC Americas’ Best Residential Solar Project of the Year.
You will not be selling a commodity. You will be building a premium field sales organization around one of the strongest roofing-to-energy upgrade platforms in the market.

Compensation

Base salary of $125,000 to $150,000, depending on experience.
Total on-target compensation of $250,000 to $350,000+ based on team production.
Performance compensation tied to team revenue, gross profit, and sales organization growth.
Health, dental, and vision insurance.
401(k).
Paid time off.
Full-time, onsite and field-based role in the Chicagoland area.
Travel may be required as Phoenix Exteriors expands this model into Nashville and Memphis.

Ideal Background

Roofing sales leadership.
Storm restoration sales leadership.
Solar sales leadership.
Window, siding, HVAC, pest control, alarm, or other D2D/in-home sales leadership.
Experience at a high-volume home improvement company with structured canvassing, setting, closing, and CRM accountability.
Experience building a field sales team that can be duplicated across multiple markets is highly valuable.

Application Requirement

To be considered, please be prepared to answer the following:

How many sales reps or canvassers have you personally managed?
What was your team’s monthly or annual revenue?
What was your average close rate?
What was your average appointment set rate or inspection rate?
What CRM did you use?
How did you recruit, train, and hold reps accountable?
What sales team did you build that still performs because of your system?
Have you opened, expanded, or helped scale sales teams into new markets?

If you are a proven field sales leader who can build a real canvassing and closing machine, Phoenix Exteriors is ready to give you the platform, products, brand power, and compensation opportunity to win.

https://careers.hirebus.com/jobs/f3323c4e-f75a-4c4d-b8e5-e375caab40fa

Job Type: Full-time

Pay: $125,000.00 - $350,000.00 per year

Benefits:

401(k)
Dental insurance
Health insurance
Life insurance
Paid time off
Vision insurance

Experience:

Sales: 1 year (Preferred)

License/Certification:

driver's license (Required)

Work Location: On the road

Quick Apply

Refine Your Search

head of sales jobs in chicago il

Director of Field Sales: Tesla Energy, Roofing & Home Improvement

Senior Director, Partner Sales

Director of Sales & Marketing, Independent Senior Living

Director Area Independent Living Sales

Head of Sales, Central

Founding Head of Enterprise Sales

Regional VP of Sales – Power Distribution

Head of SMB Sales, Grocery & Retail (US&C)

Head of Sales Strategy - Grocery

Head of Industry, Retail, Large Customer Sales

National Sales Director (East)

SVP, Client Sales & Insights - Mid-Market National Team Lead - (Remote, Chicago preferred)

Director of Sales Training - High Ticket

Senior Director, Head of Convenience Retail & On-Premise Sales

Director, Grocery Sales-Central

Head Of Sales

Sales Director, Product Specialists (Smart Trailers)

High Ticket Sales Director

Director of Sales & Marketing - Hotel 55 Chicago

Executive Director Head of Americas Retail Sales and Distribution

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