Chief Operating Officer & Head of Sales

Mason Finance, San Francisco, CA

Better Tools. Better Information. Better Retirement.

Cherry Installments is a FinTech company making it quick and simple for direct-to-consumer businesses to grow their sales by offering installments as a payment option.

We know that every sale counts. We believe everyone should have the tools to win every sale. We hire the world’s best and brightest people to make this future a reality.

Cherry is backed by an all-star lineup of investors such as DCM and early Tesla board member and eBay Motors Founder Simon Rothman. Cherry was founded and is led by Stanford entrepreneurs with years of experience in Technology, Sales and Finance.

Are you a team-player and a great communicator? Extremely strong operator and sales person? Do you want to join a rapidly growing team and company? Keen to help build the foundation of the greatest FinTech for SMBs?

Then come join the Cherry team!

This role is on the front lines of the Cherry growth: building and managing our operations and our sales organizations.
You'll be running the day to day operations of the company while building a sales organization that on-boards our customers (small to medium business owners, sales people, etc.) and maintains our customer base.

What You'll Do?

  • Own and manage an the company's day to day operations
  • Own and manage the company's expansion into new states
  • Develop and implement our operations systems, processes, and personnel to achieve Cherry's rapid growth objectives
  • Build, own and manage the company's sales organization on-boarding SMBs and managing the existing customer base
  • Build, own and manage the company's customer support organization (merchants and consumers)
  • Motivate and lead a high performance team; attract, recruit a new operations and sales team
  • Directly oversee operations and sales and partner with the CEO on sales management

What You Need?

  • Ability to get things done in a startup environment
  • 2+ years experience in executive operations and/or sales leadership positions
  • Self-starter and highly motivated, bias towards taking initiative
  • Leadership skills, with steadfast resolve and personal integrity
  • Understanding of advanced business planning and regulatory issues
  • A solid grasp of data analysis and performance metrics
  • Bachelor’s degree
  • FinTech and/or startup experience a plus!


  • Perks: Health, Dental, Commuter, 401k Benefits
  • Compensation: Competitive salary and equity package, varies with experience
  • Training, mentorship and coaching from leadership
  • Fun, diverse, open-minded coworkers
  • Contact: Any questions contact us at [email protected]
This position is full-time and based in San Francisco.

Cherry provides equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local law.

About Mason Finance

Mason Finance was founded on the idea that access to the right information and excellent financial services has no retirement date. Everyone, regardless of age, deserves honest financial products that are designed for them. We have a passion for technology but an even deeper desire to help people get more out of their lives. Living longer is one of our greatest accomplishments but millions of people aging in poverty threatens its legacy. We’re spreading the word about the option to sell your life insurance because we know that many people surrender or lapse their policies without the knowledge of a life settlement. This keeps us up at night. At Mason Finance we believe in the power of information, life settlements, viatical settlements, and annuities to empower people to take control of their financial lives as they age.

Mason Finance

Want to learn more about Mason Finance? Visit Mason Finance's website.