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Senior Account Executive; AE

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: Widewail
Full Time position
Listed on 2026-10-31
Job specializations:
  • Sales
    Business Development, B2B Sales, Sales Representative, Account Manager
Salary/Wage Range or Industry Benchmark: 80000 - 100000 USD Yearly USD 80000.00 100000.00 YEAR
Job Description & How to Apply Below
Position: Senior Account Executive (AE)

Widewail is the automotive customer intelligence platform that turns dealership reviews and customer feedback into weekly operating priorities for the franchise dealerships, dealer groups, and OEMs. Founded in Burlington, Vermont in 2018, it generates, responds to, and interprets the voice of the customer, powered by the Widewail Index of 20 million dealership reviews.

Position Title

Sr. Account Executive

COO or VP of Sales

Direct Reports

None

Level

Sr. Account Executive

Status

Full-time, exempt

Location

Remote (US)

Compensation

$80,000–$100,000 base salary depending on experience, plus variable commission.

Last Reviewed

October 2026

Hiring in the following states: Arkansas, California, Colorado, Connecticut, Florida, Georgia, Maine, Massachusetts, Minnesota, New Hampshire, New Jersey, New York, North Carolina, Pennsylvania, Texas, Vermont.

Position summary

The Senior Account Executive (Sr. AE) will focus on growing Widewail's customer base by building strong relationships within a named book of dealer clients, consisting of groups with 6+ rooftops. It will be your responsibility to prospect within your account base, set and run demos with prospective clients, manage and grow partnerships with existing clients, and maintain a robust pipeline that sets you up for successful achievement of revenue targets.

You should be comfortable presenting to and communicating with C-Level Executives and large groups of potential clients. If you love fast-paced environments, collaboration, and the thrill of helping businesses succeed, this role is for you.

Objectives:

In your first 6 weeks, onboard, ramp up, and build a solid sales foundation:
  • Connect with Sales, Marketing, and Product teams to understand Widewail’s offerings and why dealerships trust us.
  • Learn our sales process, messaging, and competitive positioning by shadowing top performers.
  • Get hands-on with our CRM, mastering lead tracking, metrics, and outreach  your first 3 months, start driving revenue:
  • Create, preserve, and grow relationships within a designated book of business through prospecting, sales calls, and rapport-building
  • Schedule and run client meetings, ensuring a steady flow of qualified opportunities
  • Identify and close cross-sell/up-sell opportunities using the Widewail suite of products
  • Accurately forecast monthly sales achievement to management
  • Contribute feedback to the larger Widewail organization by utilizing strong analytical thinking, presentation, and problem-solving skills
Within 6 months, become a top-performing AE and a trusted resource for your team:
  • Help refine our sales process by identifying common objections and sharing insights
  • Partner with Marketing and Sales Leadership to enhance outreach strategies
  • Use your expertise to help our Product team develop future offerings

Performance measures

The Account Executive is evaluated primarily on:

  • Pipeline coverage — qualified opportunity in the funnel against the coverage ratio required to make the number.
  • Forecast accuracy against monthly commit.
  • Activity and conversion: meetings set, demonstrations run, and demonstration-to-close rate.
  • Book health: retention and expansion within the assigned accounts.
Competencies
- What we are looking for:
  • Sales Hustler & Relationship Builder – You thrive on making connections, starting conversations, and creating excitement around our solutions.
  • Prospecting Pro – You're comfortable reaching out to people who may not know us yet—and you know how to turn cold outreach into a warm conversation
  • Driven & Goal-Oriented – You love a challenge, set high targets, and are relentless in achieving them
  • CRM & Organization Master – You document your work, track your pipeline, and stay on top of your deals with precision.
  • Team Player – You partner closely with product, marketing, and…
Position Requirements
10+ Years work experience
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