Head of Sales, Checkr Pay

About Checkr

Checkr builds people infrastructure for the future of work. We believe everyone should have a fair chance to work. That's why we've designed a faster—and fairer—way to screen job seekers. Established in 2014 and valued at $5B, Checkr puts modern technology powered by machine learning in the hands of hiring teams, helping thousands of companies like Uber, Instacart, Netflix, Compass Group, and Adecco to hire great new people with an experience that’s fast, smooth, and safe.

A career at Checkr means collaborating with brilliant minds, disrupting an industry, and opening channels of employment to often overlooked candidates. Checkr has been recognized as one of BuiltIn's 2023 Best Places to Work in the US and is a Y Combinator 2023 Breakthrough Company and Top Company by Valuation.

About The Team/Role
Head of Sales, Checkr Pay will be responsible for securing rapid and continued growth for Checkr Pay, an instant payments solution for flexible workforces. They will manage a small but growing team of account executives supporting our Pay customers, and will be tasked with continuing to build and scale the team. Additionally, this leader will be responsible for developing our Pay sales strategy overall, iterating on who and how we sell, and learning how we need to change the product to best support those customers, all while coaching AEs to enable the entire team to be effective.

This leader will report to the SVP of Sales, partnering closely with the Head of Checkr Pay, and will be the driving force for building out an organizational culture of scrappy, resourceful sales, relentless continuous improvement, and a commitment to speed. Pay is a bold, ambitious bet that is separate from Checkr’s background check business, and we will need to harness agility and speed in the face of ambiguity to be successful. With limited go-to-market support, the right candidate will need to get extremely hands-on to create whatever solutions are needed to drive success.

This person will also be charged with developing & establishing strategic relationships with key internal stakeholders across product, marketing, and revenue operations teams, as well as with external business partners, refining sales processes & strategy, identifying & securing new business opportunities, growing & managing existing business, as well as hiring & retaining talent. They will help define a clear vision for how Checkr Pay can capture greater market share and will lead the execution of the plan to enable exponential, hockey-stick growth.

What You’ll Do:

• Develop entire GTM strategy & execution with Head of Checkr Pay.
• Lead strategy within as it relates to new logo hunting, accelerating Checkr Pay sales and driving exponential growth in customer acquisition.
• Responsible for managing and leading a small team of AEs, ensuring productivity, goal achievement, and team development.
• Participate in the development of the strategy to land and expand new Checkr Pay logos while closely collaborating with product and engineering to identify opportunities and potential gaps.
• Achieve and hold teams accountable for revenue objectives & Key Performance Indicators (KPIs).
• Establish and maintain a strong sales culture that promotes teamwork, accountability, and a focus on achieving results, while also emphasizing the speed and agility needed at this stage of the product life cycle.
• Partner cross-functionally to refine and implement go-to market strategies as well as influence the development of products to take to market.
• Increase productivity by relentlessly improving processes, systems, & tools.

• Minimum of 5-7 years of sales management experience at Seed, Series A, or Series B startups.
• Experience working with cross-functional teams (Marketing, Product, Finance, Customer Success) to achieve ambitious company objectives.
• Strong business acumen; ability to deeply understand customers and their problems, and to tailor solutions to help drive business value.
• Advanced in dealing with ambiguity and complexity in order to navigate uncertainty and lead teams through change.

• Experienced with complex sales processes, proposal development and oral presentations that win new business.
• Highly motivated and results-driven with consistent achievement of quota(s) across multiple periods of time.
• Highly collaborative and able to build strong cross-functional partnerships.
• Ability to work in a fast-paced, high-pressure environment and adapt to rapidly changing business needs.
• Flexibility and ability to juggle and complete multiple priorities and projects (internally and externally) in a fast-paced environment.
• Strong leadership: active listening, interpersonal and presentation skills.
• Exceptional communication skills both verbal and written.
• Self-starter, who can establish and organize activities working independently.

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive compensation and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend, home office stipend