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Remote, Oregon, United States
Remote only
About Cherry
Started in 2019, Cherry is an extremely fast growing FinTech that has built the simplest, fastest, and most inclusive Buy Now, Pay Later solution for medical practices such as dentists, medical aesthetics, veterinarians etc.
Cherry enables medical practices to treat more patients by making their services more financially accessible.
Cherry was founded and is led by Stanford entrepreneurs with a previous successful exit and backed by an all-star lineup of investors such as Kleiner Perkins and DCM.
About the Role
We are seeking a strategic and results-oriented Senior Sales Sales Manager to lead a team of Account Executives responsible for driving revenue growth across our Health & Wellness and Beauty & Spa segment. In this role, you will be accountable for team performance, pipeline health, and execution against key sales metrics.
You will play a critical role in scaling our go-to-market strategy by strengthening outbound efforts, improving conversion across the funnel, and developing a high-performing sales culture. This position offers the opportunity to directly influence revenue outcomes while coaching and developing top sales talent within a rapidly growing organization.
Your sales team will consist of Account Executives that will be accountable for bringing in new business within the assigned vertical, ensuring those businesses experience success in the first 60 days of partnering with us, and collaborating with our onboarding, customer success, and sales operations teams.
The position will be remote, with occasional travel required for on-site sales pitches, team building events, and sales events.
Responsibilities
Recruit, hire, and develop a high-performing team of 8-12 capable of navigating complex, multi-stakeholder deals
Actively source and close top talent, raising the bar with each hire
Lead structured onboarding to ramp reps on sales cycles, deal strategy, and value-based selling
Operate as a true sales coach—reviewing calls, deal strategy, and pipeline in detail to elevate rep performance
Coach reps on complex deal navigation, stakeholder mapping, and executive-level conversations
Reinforce and operationalize proven methodologies (e.g., Challenger, MEDDICC, GAP) in a SMB context
Run weekly 1:1s focused on pipeline quality, deal progression, and closing strategy
Actively engage in key deals to support negotiation, positioning, and closing efforts
Build a culture of accountability, continuous improvement, and winning
Own team performance against pipeline generation, conversion rates, average deal size, and revenue targets
Drive disciplined pipeline management, ensuring accurate forecasting and consistent deal progression
Elevate win rates by improving qualification, deal strategy, and multi-threading across accounts
Hold the team accountable to high standards through performance management and clear expectations
Maintain full accountability for monthly, quarterly, and annual revenue targets
Set clear quotas, KPIs, and operating rhythms aligned to sales motions
Partner with Sales Ops, Marketing, and RevOps to improve lead quality, routing, and conversion across the funnel
Collaborate cross-functionally with onboarding and customer success to ensure strong handoffs and long-term customer value
Identify and implement initiatives that improve sales efficiency, shorten sales cycles, and increase deal size
Forecast accurately and consistently, providing visibility into risks and opportunities
Lead by example—operating with ownership, accountability, and a bias toward action
Proven top 10% performer in an individual contributor sales role, with success in SMB or complex sales environments
1-2+ years of experience as a Manager in SMB preferred
Demonstrated ability to lead from the front—especially during periods of change, ambiguity, or performance pressure
Strong deal strategist with experience managing longer sales cycles and multiple stakeholders
Track record of proactive ownership—bringing solutions, not problems
High energy, competitive drive, and the ability to motivate and inspire a team
Experience helping recruit, mentor, and elevate top talent
Alignment with Cherry’s core values: Practice Obsessed, Be An Owner, Seek Truth Through Facts, and Celebrate Excellence
Willingness to be measured and compensated based on team performance
Advanced experience in prospecting, lead-generation, and implementation of selling processes/methodologies, such as SPIN Selling, the Challenger Sale, MEDDICC, or others
Exceptional written, verbal, and technical communication skills
Independent worker, self starter, and proven ability to exceed expectations in a remote work environment
Willingness to work at a dynamic, ever-changing environment filled with friendly competition where high performance is directly rewarded
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.
