About the team

As a Sales Manager, Mid Market – Existing Business, you will play a critical role in driving Company’s growth by leading the strategy, execution, and optimization of our go-to-market efforts with existing Mid Market customers. In this role, you will focus on deepening relationships, expanding product adoption, and maximizing customer value across Company’s growing Mid Market base. You will lead a team of high-performing Account Executives, supporting their development while also engaging directly with strategic accounts.

We are looking for a proactive and customer-obsessed leader who thrives in a high-growth, ambiguous environment. You’ve successfully managed and scaled high-performing teams and know how to drive impact by balancing strategy, execution, and hands-on leadership.

• Lead, coach, and grow a team of Account Executives focused on driving revenue growth from Company’s existing Mid Market customers.
• Own performance against key growth and retention metrics, including expansion, cross-sell, and renewal targets.
• Partner with senior leadership to refine the long-term strategy for Company’s existing business sales motion.
• Support Account Executives in developing consultative, solution-oriented approaches to expand customer adoption of Company’s products and services.
• Foster a high-performance, inclusive team culture that emphasizes learning, ownership, and measurable impact.
• Collaborate cross-functionally with Product, Marketing, Customer Success, and other teams to improve customer experience and retention.
• Personally engage with key accounts, including executive-level stakeholders, to build lasting partnerships and drive long-term value.
• Advocate for the needs and feedback of existing customers to inform Company’s product roadmap and strategy.
• Who You Are
• We’re looking for someone who meets the minimum qualifications listed below. If you meet these, we encourage you to apply — preferred qualifications are a bonus, not a requirement.
• Minimum Requirements
• 5+ years of relevant sales experience.
• 2+ years of experience leading a team of quota-carrying sales professionals.
• Proven track record of driving revenue growth through expansion and retention within an existing customer base.
• Demonstrated ability to hire, develop, and manage high-performing sales teams.
• Strong executive presence and ability to build and maintain relationships with senior customer stakeholders.
• Comfort working with technical products and the ability to translate complex concepts into business outcomes.
• This role requires working from the Chicago office three (3) days per week.
• Experience working in a growth-stage internet or software company.
• Track record of managing complex sales cycles and driving multi-product adoption.
• Experience managing teams in offices outside of company headquarters.
• Familiarity with payments or fintech industry and related customer needs.