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Director Enterprise Sales

Remote position, United States only

$150k - $300k


Are you a talented and motivated hunter with a passion for sales and innovation? Sezzle, a cutting-edge fintech company, is seeking a Director of Enterprise Sales to drive net new sales and revenue growth within the largest retailers in the US. As a key player in the payments space, Sezzle aims to financially empower the next generation and invest in social good. In this role, you'll engage with multichannel and pureplay ecommerce merchants, selling to C-level executives and leaders in payments, marketing, ecommerce, and IT. With a focus on establishing Sezzle as the Buy Now Pay Later provider of choice for enterprise retailers, you'll utilize creativity and partnership to implement win-win deal structures. If you have a proven track record in enterprise sales, a strong understanding of the payments landscape, and exceptional communication skills, this fast-paced and dynamic environment could be the perfect fit for you. Join Sezzle's rapidly expanding team and make a positive impact on the world while advancing your career. Apply now!

Job Description

Our Company

Sezzle is a cutting-edge fintech company whose long-standing mission is to financially empower the next generation. Only one in three millennials own a credit card, and the vast majority of millennials possess a subprime credit score or no score at all. To address these problems, Sezzle has built a payment platform that increases purchasing power for consumers by offering interest-free installment plans at online stores. This increase in purchasing power for consumers leads to increased sales and basket sizes for the numerous eCommerce merchants that currently work with Sezzle.

As the first and only B-Corp in the payments space, Sezzle’s goal is to help everyone pursue financial freedom, and to invest in social good and ethical initiatives that shape a better world.

At Sezzle, we’re committed to putting purpose alongside profitability. We work hard to maintain rigorous standards of social and environmental performance, accountability, and transparency to build a better world. The employees at Sezzle lean into significant societal and cultural shifts, ensuring internal and external focus on positive impacts that benefit our community.

The Position:

As the Director of Enterprise Sales, you will play a crucial role in driving net new sales and revenue growth within the largest retailers in the United States.

In this position, you will be responsible for engaging with multichannel and pureplay ecommerce merchant prospects. You will be selling to C-level executives and leaders in payments, marketing, ecommerce, and IT. You will report directly to the SVP of Enterprise Sales and Partnerships.

Your primary objective will be to establish Sezzle as the Buy Now Pay Later provider of choice for enterprise retailers by ensuring the adoption, implementation, and growth of Sezzle among retail merchants.

We are seeking a talented and motivated hunter who is skilled in forging partnerships and utilizing creative deal structures to achieve win-win outcomes. This role offers the opportunity to work in a fast-paced, dynamic environment as part of a rapidly expanding team, with additional potential for career growth.

What You'll Do:

  • Drive net new sales and revenue growth by targeting and engaging with the largest retailers in the US.
  • Build and develop a pipeline of retail targets including fashion and apparel, health beauty, sporting goods, baby kids, hobby, entertainment, mass merchant, marketplaces and everyday spend.
  • Utilize creativity and partnership to implement win-win deal structures that empower customers to achieve their revenue, conversion, and innovation goals.
  • Lead all aspects of the selling process from prospecting to launch.
  • Meet or exceed targets for revenue and sales activity.
  • Partner with cross functional teams at Sezzle including Marketing, Product, Technology, Legal and Merchant Success
  • Stay up to date with industry trends and competitors to identify new opportunities and maintain a competitive edge.
  • Act as a vertical subject matter expert within Sezzle and represent Sezzle externally including at important industry events. Guide Sezzle’s commerce strategy and advocate for solutions, features and specific use cases.
  • Create articulate compelling value propositions around Sezzle’s solution.
  • Consistently surpass merchant expectations with a consultative approach.

What We Look For:

  • Proven track record in enterprise sales, preferably within the retail or ecommerce industry.
  • Strong understanding of the payments landscape, particularly in the Buy Now Pay Later space.
  • Experience driving technology adoption and creating long-term transformational account strategies
  • Ability to think strategically and provide innovative solutions to customer challenges
  • Demonstrated success in identifying, developing, negotiating, and closing payments/ecommerce/technology solutions with complex enterprise accounts
  • Strong teamwork and collaboration skills, with the ability to work effectively in a cross-functional environment.
  • Exceptional communication and presentation skills, both verbal and written.
  • High level of self-motivation and a results-oriented mindset.
  • Experience working with and presenting to C-level executives
  • BA/BS degree, MBA preferred

About You

  • You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
  • You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
  • You have a bias for action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
  • You earn trust - you listen attentively, speak candidly, and treat others respectfully.
  • You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.
  • You deliver results - you focus on the key inputs and deliver them with the right quality and in a timely fashion. Despite setbacks, you rise to the occasion and never settle.

What Makes Working at Sezzle Awesome?

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators; we are skilled musicians, yogis, cyclists, chefs, golfers, dog-lovers, and rock-climbers. We believe in surrounding ourselves with not only the best and the brightest individuals, but those that are unique and purpose-driven in all that they do. Sezzle recognizes and values the importance of diversity and inclusion in enriching the employment experience of its employees and in supporting our mission.

Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire.

Perks Benefits:

  • Competitive salary and RSUs
  • Generous paid time off, sick time and volunteer hours
  • Life, STD/LTD, medical, dental and vision insurance
  • Highly discounted LifeTime gym membership
  • Work From Home stipend
  • 401k with match
  • Collaborative fun workspace
  • The opportunity to join Minneapolis’s fastest growing startup alongside a team of motivated and driven individuals

Diversity and Inclusion

Sezzle provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, creed, gender, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender identity, national origin, age, disability, genetic information or characteristics, marital status, familial status, veteran or military status, status regarding public assistance, membership or activity in a local commission, or any other protected status in accordance with applicable federal, state and local laws. Sezzle recognizes and values the importance of diversity and inclusion in enriching the employment experience of its employees and in supporting our mission.


The compensation range for the role is $150k - $300k OTE including base and variable. Our ranges are very broad to accommodate all types of candidates and encourage growth. Specific compensation offered to a candidate may be dependent on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside of the posted ranges.


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