Director, Enterprise Sales
Loop Returns
Sales & Business Development
Chicago, IL, USA
Posted on Jul 11, 2025
The Sales Team at Loop is the engine that powers the business. In an ever evolving market and company, the sales team seeks to provide revenue and stability that can accelerate our vision to market. You will join an already existing (and awesome!) team of Enterprise & Strategic Account Executives, who you’ll enable to grow and operate more effectively.
Right away, we’ve listed what we think you’ll be spending your time on. We’re growing fast, and growth means the challenges we’ll work on together will change as we lead Loop through new and different phases.
At Loop, we’re intentional about the way we work so that we can do our best work. We call this our Blended Working Environment. We work from our HQ in Columbus, OH, or one of our Hub or Secluded locations, and are distributed throughout the United States, select Canadian provinces, and the United Kingdom.
For this position, we’re looking for someone to join us in Chicago, IL; Columbus, OH; or New York City, NY. However, we welcome applications from qualified individuals in other locations.
What you'll do:
- Foster an energetic, inclusive, and supportive sales environment where your team can thrive.
- Build deep expertise in our market by understanding key players, buyer pain points, and how our platform delivers value to merchants.
- Collaborate with Marketing, Sales Development and Partnerships on an account-based strategy to achieve pipeline targets, improve positioning, and customer storytelling.
- Forecast with confidence and clarity, sharing your insights from both an objective and subjective point of view.
- Monitor team performance by tracking leading indicators and outcomes, using insights to identify growth opportunities and help the team continuously improve.
- Provide timely and personalized coaching to help AEs ramp quickly, build confidence, and succeed in their roles.
- Equip the team with training on product knowledge, competitor insights, and sales methodology while reinforcing adoption of our standard frameworks and tools.
- Foster strong collaboration by navigating challenges with peers and offering constructive feedback across the GTM org.
- Keep the team aligned on individual, team, and company priorities while ensuring they have visibility into key go-to-market updates and resources.
- Celebrate both wins and lessons learned by creating space for reflection, recognition, and continuous improvement.
- Support strategic planning through annual budgeting, quarterly capacity planning, and retrospective analysis of performance and outcomes.
- Recruit, develop, and retain top talent by leading career conversations, setting clear performance measures, and supporting growth across the go-to-market organization.
- Make decisions guided by Loop’s core values: Be a Human First, Make Merchants Successful, Own the Outcome, and Courage Over Comfort.
Your Experience:
- We’ve outlined the experience we believe will help set you up for success in this role. That said, we know different people approach challenges in different ways, and we don’t expect everyone to fit neatly into a box of requirements. If you’re excited about this role, we encourage you to apply, even if you don’t meet every single qualification.
- 5+ years of B2B SaaS sales experience is required; experience in ecommerce or logistics is a strong differentiator.
- You’ve built and led teams of Account Executives, supporting them through different stages of growth.
- Demonstrated ability to develop strategies, identify the work that needs done to carry them out, and ensure quality delivery of that work.
- You’ve worked at a startup company (or a few) and know what it means to make it through the various stages of rapid growth.
- You have been trained in MEDDICC, Challenger, Command of the Message, Winning by Design or some other standard sales methodology.
- You have examples to share of how you have improved and operationalized sales best practices.
- You have pushed your team to leverage AI and created a culture with a growth mindset, adopting new ways of working and delivering results.
- Experience recruiting, hiring, and developing high-performing teams, leading and motivating them through change.
- You’ve created exceptional partnerships with internal and external stakeholders, and quickly became one of their favorite people to work with.
#LI-JG1
Loop Story
In a perfect world, Loop wouldn't exist. If we had our way, we'd live in a world where we're mindful about how we consume, we love every product we own, and we share values with the brands who create them. In reality, commerce isn't perfect and often breaks. Loop creates second chances.
We're starting by revolutionizing the post-purchase experience. We've taken one of the most fragile commerce interactions - returns - and turned it into something consumers actually love, and that deepens our connection to brands and products.
We take connection seriously on the inside, too. We're building a work experience that allows you to Be A Human First and prioritizes empathy and wellbeing. We view Loop as a special place in your career to shape the future of an industry and become a better person while doing it. You can grow faster here in a shorter amount of time - we'll give you space and trust you to fill it.
