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Senior Director, Enterprise Sales



Sales & Business Development
Remote · United States
Posted on Wednesday, September 27, 2023

About Checkr
Checkr’s mission is to build a fairer future by designing technology to create opportunities for all. We believe all candidates, regardless of who they are, should have a fair chance to work. Established in 2014 and valued at $5B, Checkr is using technology to bring hiring to the next level. Our People Trust Platform uses machine learning to help thousands of companies modernize their background check process and make hiring safer, more efficient, and more inclusive. Some of our customers include Uber, Instacart, Doordash, Netflix, Compass Group, and Adecco.

A career with Checkr is an opportunity to work with some of the best and brightest minds, disrupt an industry for a better future, and give otherwise overlooked candidates access to employment. 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.

Senior Director, Enterprise Sales will be responsible for securing rapid and continued growth in Checkr’s Enterprise segment (10-100K employee size). This specifically includes the responsibility to manage a team of enterprise account executives supporting these customers and the ability to continue to build and scale the team. Additionally, this leader will be responsible for pushing us up into the Enterprise by coaching AEs focused on Enterprise inbound demand + a list of outbound targets.

This leader will report to the SVP of Strategic Sales, and entrusted with the largest customers and new logos and will be the driving force for building out an organizational culture of cross-functional mentorship & relentless continuous improvement focused on expansion and growth through customer centricity.

This person will also be charged with developing & establishing strategic relationships with internal key stakeholders across the 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 can capture greater market share and will lead the execution of the plan to enable exponential growth.


  • Participate in the development of the strategy to accelerate Enterprise sales and growing existing customers, while identifying areas of expansion in the market
  • Drive strategy within the enterprise segment as it relates to both new logo hunting and account management
  • Responsible for managing and leading a team of 6 to 9 Enterprise AEs, ensuring productivity, goal achievement, and team development
  • Participate in the development of the strategy to land and expand Enterprise new logos while closely collaborating with product and solution engineers to identify opportunities and potential gaps
  • Achieve and hold teams accountable for revenue objectives & Key Performance Indicators (KPIs)
  • Build quality, excellence, and depth into the Named reps and managers
  • Establish key relationships with clients across the United States
  • Establish and maintain a strong sales culture that promotes teamwork, accountability, and a focus on achieving results
  • Partner cross-functionally to refine and implement go-to market strategies as well as influence the development of new products to take to market
  • Increase productivity by relentlessly improving processes, systems, & tools

Key Functional Competencies

  • New Logo prospecting experience
  • Objection Handling
  • Business Foundations
  • Industry Foundations
  • Value Discovery
  • Point of View Development
  • Account Team Alignment
  • Executive Alignment
  • Forecasting
  • Value Realization
  • ROI Positioning
  • Exceptional Communication skills both verbal and written

What you bring:

  • Minimum of 5-7 years of Enterprise Sales management experience
  • You have a passion for growing and supporting businesses and be a true customer advocate both internally and externally
  • High Growth tech company experience, preferred
  • Experience working with cross functional teams (Marketing, Product, Finance, Customer Success) in a matrix environment to achieve company objectives
  • Enthusiastic willingness to travel ~30%
  • Experience navigating and leading multi million dollar contract negotiations
  • Strong business acumen, with experience working with large brands
  • Advanced in dealing with ambiguity and complexity in order to navigate uncertainty and lead the team through change

Required Skills:

  • Deep experience liaising with senior-level stakeholders, identifying opportunities and strategies for business growth
  • Experienced with a complex pursuit process, 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 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
  • The ability to work well under pressure
  • Self-starter, who can establish and organize daily activities working fully independently

One of Checkr’s core values is Transparency. To live by that value, we’ve made the decision to disclose salary ranges in all of our job postings. We use geographic cost of labor as an input to develop ranges for our roles and as such, each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but we will specify the target range for an exact location when you are selected for a recruiting discussion. For more information on our compensation philosophy, see our website.

The salary range for this role is $250,000 to $500,000.

Equal Employment Opportunities at Checkr

Checkr is committed to hiring talented and qualified individuals with diverse backgrounds for all of its tech, non-tech, and leadership roles. Checkr believes that the gathering and celebration of unique backgrounds, qualities, and cultures enriches the workplace.

Checkr also welcomes the opportunity to consider qualified applicants with prior arrest or conviction records. Checkr’s commitment to diversity extends to hiring talented individuals in spite of a prior criminal history in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance.