Account Executive, Check for Staffing Platforms, Talent Marketplaces and EORs

Check for Staffing, Talent Marketplaces, and EORs is the second official segment of Check’s growing payroll infrastructure platform. We operate as a startup within a startup and have grown 10X over the last 6 months. We aim to help worker platforms run their own payroll with code, leveraging our infrastructure. Staffing platforms and talent marketplaces power the growing gig economy and are completely transforming how workers find jobs. However, they are held back by outdated payroll infrastructure, which our scrappy team aims to transform. Through the use of our APIs, we’ve already proven these platforms can increase retention, grow conversion, and reduce support by embedding payroll, and we’re looking to scale up this business dramatically. 

For this role, we are seeking a senior Account Executive with an entrepreneurial mindset, technical sales expertise, and high integrity. As the first dedicated Account Executive for this new business unit, this individual will own going after multi-million dollar strategic accounts, building the foundation of our sales strategy, and working with the team to grow this new segment within Check.

In this role, you will:

• Sell to strategic accounts in the Check for Staffing, Talent Marketplaces, and EOR segment, from multi-hundred thousand dollar deals up to multi-million dollar deals
• Support all aspects of deal execution, including outbound efforts, sales execution, internal management, and contract execution
• Develop long-term relationships with C-level executives at prospects 
• Work with stakeholders across the Check organization in product, compliance, operations, and more to secure what is needed to close strategic deals
• Report on key metrics and communicate actionable customer and partner feedback to Check’s product, engineering, and exec teams
• Work as a member of the Check for Staffing, EORs, and Marketplace team to help grow this internal startup within Check
• Develop new strategies for improving outbound and deal execution

Many backgrounds could fit this role, but ideal candidates will have some or all of the following:

• 7-10 years of work experience, with at least 4+ years of experience selling in technology enterprise sales (founder backgrounds are accepted and encouraged)
• Direct experience closing large strategic accounts that involve 6+ month-long sales cycles and ARR of greater than $200K
• Experience building relationships with C-level executives and managing accounts with multiple stakeholders
• Executive presence, clear and concise communication style
• Experience managing  a complex enterprise sales motion
• Experience working at an early-stage startup (<50 people) or within a startup environment at a larger organization
• Experience working with technology infrastructure or fin-tech infrastructure preferred
• Can creatively and persistently network in order to locate decision-makers, build relationships, negotiate and sell
• Are technologically savvy and familiar with APIs
• Have exceptional communication skills and the ability to rally organizational alignment
• Bring a high energy level to match Check’s fast-paced, start-up environment!

What we offer:

In the US, Check offers company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage to all full-time employees, effective on their first day of work. We also provide stock options, flexible PTO and sick leave, 16 weeks of fully paid parental leave for all new parents and flexible return-to-work, 9 annual holidays, a 401k retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses. Benefits may vary outside the US.

The expected annual salary for this role is between $161,000 and $181,000, dependent upon each candidate’s unique experience and qualifications. Additionally, this role is expected to be eligible for performance-based compensation of $69,000 to $77,600 in the form of commission bonuses.