Sales Development Representative

WinsAbove; Chicago (IL); On-site; USD 50,000 - 70,000; Full time

Job summary

WinsAbove is looking for a Sales Development Representative (SDR) to join their team in Chicago, IL. This role is focused on connecting prospective customers with Stripe's products through various outreach methods, including cold-calling and email. Success in this position will require superior communication skills and a self-starter attitude, with in-office participation expected 3-4 days a week.

The SDR will also benefit from a structured onboarding program designed to develop necessary skills for a successful career in sales.

Qualifications

• Demonstrated track record of top performance in various endeavors.
• Ability to clearly articulate complex topics verbally and in writing.
• Motivated individual capable of operating autonomously.

Responsibilities

• Contact potential customers via cold-calling and email.
• Book meetings and pitch Stripe’s products to prospects.
• Research and create outreach materials for high-value prospects.
• Follow up with customers who have shown interest.
• Update activity in the CRM consistently.

Skills

Verbal communication skills

Written communication skills

Self-starter

Customer engagement

Tools

Salesforce

Job description

About the team

Note: This role is an in-office position, based in our Chicago, IL office.

As a Sales Development Representative (SDR) at Stripe, you’ll work in a customer-facing role focused on connecting prospective customers with Stripe. You will work in partnership with the Marketing and Sales teams to create a high quality, predictable pipeline. We hire and train SDRs in a way that prepares them to be a high performing source of talent for Stripe Sales and Go to Market teams.

What you’ll do

For the first few months, you’ll be a part of our Sales Development Associate program, which is designed to accelerate onboarding and support new grads transition into their first roles in a corporate setting. Part of this period will be supported by the Sales Development Academy which will help you quickly build and develop the foundational skills required to be successful in this role and position you for a long-term career in Sales at Stripe. Through a mix of virtual sessions, in-person practicums, and check‑point quizzes, you’ll learn all about Stripe’s products and how to be a successful SDR. During this period you’ll also be partnered with a senior SDR on the team as a mentor. Along with your manager, your mentor will be there as an additional resource to help support you.

Within a few weeks of starting at Stripe you'll be reaching out to potential Stripe customers, pitching them on the products that could best support their business model, and partnering with senior sellers on the team who will ultimately help close deals. We take a data driven approach to the role and the success of our SDRs is largely dependent on their successful outreach to new Stripe customers.

While onboarding spans across the course of your first few weeks at Stripe, the Academy offers continued training and enablement over the course of your first year as an SDR to ensure top performers are set up for a successful transition to other roles on the sales team. Most regularly we see our top performing SDRs promoted into Account Executive roles.

If you enjoy working in a fast‑paced environment, interacting with customers, and being responsible for generating revenue, we’d love to hear from you!

Responsibilities

• Contact potential customers through cold‑calling, email, and social channels, or by responding to inquiries generated from Marketing activities.
• Book meetings with potential customers (prospects) and pitch them on Stripe’s products that are a match for their business model.
• Develop relationships with prospects to uncover specific business needs through effective, consultative questioning to qualify interest and prepare a comprehensive hand‑off to sales.
• Research and create compelling outreach materials for high‑value prospects, in partnership with SDRs and Account Executives.
• Execute outbound sales outreach created by marketing, leveraging strategic messaging to target specific segments.
• Follow‑up with potential customers who expressed interest but did not initially result in a sales opportunity, maintaining a warm pipeline.
• Effectively manage customer outreach, consistently meeting/exceeding Service Level Agreements (SLAs), meticulously updating activity and contact information within the Customer Relationship Management system (Salesforce) to support weekly reporting efforts.
• Collaborate and provide essential feedback and insights to Marketing to help improve targeting, messaging, and overall campaign effectiveness.

Who you are

We’re looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply.

Minimum requirements

• A track record of top performance or prior success in academic, extracurricular, or professional endeavors.
• Superior verbal and written communication skills, with an ability to clearly articulate complex topics.
• Self‑starter who is highly motivated and able to operate effectively and autonomously in a hyper‑growth environment.
• This role requires in‑office participation three to four (3‑4) days per week in our Chicago office.

Preferred Qualifications

• Professional experience in a sales, customer service, or fast‑paced professional environment.