Creative Sales Leader

Job Opportunity: Creative Sales Leader @ Tearsheet

We’re not selling banner ads. We’re building the future of fintech media.

About Tearsheet

Tearsheet is a modern media company covering the intersection of finance, technology, and marketing. Our clients include Mastercard, Citi, FIS, and other major brands shaping the future of financial services. We're known for our creative content studio, industry-defining events, and high-impact media campaigns. Trusted by fintech giants, we’re expanding and hiring a new Sales Leader to help us grow to the next level.

The Role

We’re hiring a structured, creative, data driven, and entrepreneurial Sales Leader to take ownership of our sales strategy and execution. You’ll be the key driver of revenue across our media, events, and content studio products—building a pipeline, closing deals, and eventually managing a small team of SDRs and sales reps. You'll collaborate directly with our co-founders, who will support you in high-level relationships and packaging.

We’re big on vision, creativity, and relationships — we also need someone who brings the process, discipline, and follow-through to turn opportunities into scalable revenue.

If you thrive in turning smart chaos into repeatable wins, this is your stage.

Location: U.S. Based (work from home)

What Makes This Role Unique

• You’ll work with major financial brands like Mastercard, Citi, FIS, and Plaid

• You’ll shape Tearsheet’s sales infrastructure from the ground up

• You’ll partner directly with the founders, but own your process

• You’ll have flexibility in how you work—and how you're compensated

You Might Be a Fit If...

• You’re a process-driven closer who thrives in ambiguity and creates structure

• You’ve sold media, events, or creative services, especially to fintech or marketing

• decision-makers

• You’re energized by the idea of building something modern, lean, and impactful with the freedom to shape your own playbook

• You’ve managed or coached SDRs and salespeople before (or are ready to)

• You’re curious, entrepreneurial, and creative in how you develop new business

• You’re tech-savvy and comfortable leveraging best-of-breed, AI-powered tools (think:

  leveraging chatbots, integrated tools including CRM automation, proposal builders,

  outbound personalization, etc.) to scale your impact and work smarter, not harder.

• You don’t need hand-holding—but you’re coachable and collaborative

• You know how to package solutions, not just pitch products

• You can navigate both startups and enterprise clients with confidence

What Success Looks Like

• Building and managing a pipeline of $2M+ in annual opportunities

• Closing mid-sized deals ($25k–$100k+), with enterprise accounts

• Leading and mentoring a small SDR and/or sales team

• Established repeatable sales playbooks for mid-market and enterprise accounts

• Expand Tearsheet’s footprint by representing us at industry events

• Meeting with clients and prospects in person

• Being an active recognized participant in the local fintech scene

• Proactively improving our sales process, reporting, and CRM usage

• Co-creating our sales targets with senior management

Compensation

We believe the best sales pros deserve the greatest flexibility and upside. Our compensation does that and is customizable based on what matters to you:

• Base salary

• Competitive commission on direct sales

• Override commission on team sales

• Potential equity or profit share upon proven success

• Work-from-anywhere flexibility

• Other benefits tailored to your preferences (travel budget, coworking stipend, etc.)

• Health Reimbursement Arrangement (HRA) or other options to support your enrollment in the plan of your choice.