About Widewail

Widewail is a Burlington, Vermont based startup solving a key problem for many businesses -how to efficiently and effectively deliver the very best customer service experience while simultaneously influencing prospective customers to choose their business. By integrating with our client’s  business management systems, Widewail invites our client’s customers to review their recent experience, then monitors and responds to reviews on behalf of the businesses. These responses are expertly crafted to include key content that attracts new customers and improves overall local search rankings. By further collaborating with our clients, Widewail  ensures that responses to negative reviews successfully address the customer’s feedback while encapsulating the client’s voice. Our client base is growing fast and we are looking for additional team members to help us meet our growing demand by expanding our current product offerings and bringing new products to market.

About the Role:

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 11+ 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 strategies.

In 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

Qualifications:

• 4+ years of proven inside sales experience and closing ability
• Strong prospecting and cold calling skills
• Good organizational skills
• Strong internal motivation

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 the rest of the sales team to maximize success
• Resilient & Adaptable – You can handle objections, push through tough days, and continuously improve

Compensation:

• Based on experience - $170-200k annual OTE

Benefits:

• Medical, Dental, Vision, HSA, FSA, DCA
• Company funded Lifestyle Spending Account
• Employer match 401K
• Paid Parental Leave
• Sick Time Off
• Paid Time Off & Paid Holidays

At Widewail, we’re growing fast, having fun, and creating something special. If you’re ready to build a career in sales and be part of a winning team, let’s talk! 

Widewail is an equal opportunity employer (EOE) and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law.