Director, Customer Success at Checkr (Remote)

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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 in Forbes Best Startup Employers and is a top Y Combinator company by valuation.

As a Director, Customer Success you will be responsible for the strategic relationship management of a segment of enterprise & scale clients. You will ensure that customers are actively engaged and realize ROI and business value from their investment in Checkr solutions. This is a senior position (manager of managers) and the expectation is for the candidate to develop and coach a high-performing team that succeeds through collaboration, grit, and constant learning. A critical expectation is that this individual influences, leads, and delivers quantifiable business results via both direct line and dotted line / cross-functional organizations.

You will own the end-to-end customer engagement, adoption, renewal, and growth for entire sub-segments of customers and will be responsible for driving the success of our OKRs and annual scorecard. In addition, the Director, Customer Success will be expected to personally nurture and develop customer executive relationships. This individual will serve as a key evangelist both for Checkr as well as for Customer Success and is expected to operate in a proactive, forward thinking, and optimistic fashion.


  • You will hire, train, and manage a team of top-performing individuals and managers
  • You will serve as project manager and leader for critical cross-functional initiatives such as building a CS/Sales qualified lead engine or standing up Scaled programs for SMB/MM customers
  • You will successfully structure, plan, and drive the team to achieve business goals which may include metrics such as: 
    • Customer engagement (% customers engaged / Q)
    • Customer adoption/health (% customers utilizing platform, features)
    • Quantifiable business value / outcomes (% of customers >100% targets)
    • Renewal (gross retention rate)
    • Expansion (net retention rate)
    • CSAT/NPS
    • Average contract length
  • You will work closely w/ revops, finance, and sales to structure compensation & SPIFFS to reward customer health while also driving GRR and NRR goals 
  • You take high-level business goals and are able to define metrics, reports/dashboards, and executive memoranda and presentations that track progress, influence organizational behavior, drive forward-looking strategy, and identify areas of improvement. It is essential that this leader is capable of writing “board-level” memorandums and presentations

What you bring:

  • You are flexible and able to juggle and complete multiple priorities and projects (internally and externally) in a fast-paced startup environment
  • Experience with the background/credit check industry or the interest and aptitude to learn complex concepts that touch upon technology, the law, and public policy
  • Minimum 10+ years of proven customer success, sales, and/or consulting experience with increasing levels of responsibility, including as a manager of managers
  • Previously owned and successfully grew a $20MM+ book of business
  • Professional experience in a software / SaaS environment
  • Excellent organization, project management, and time management skills
  • Experience in building successful senior-level business relationships and facilitating conversations at all levels, including the C-suite
  • Superior verbal and written communication skills
  • You learn quickly and are excited to take on challenging new projects
  • General knowledge of software applications (i.e. Salesforce, Zendesk, Google Apps)

What you get:

  • 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

The base salary for this position will vary based on geography and other factors.  In accordance with Colorado law, the base salary for this role if filled within Colorado is $187,850 - $221,000.

The base salary for this position will vary based on geography and other factors.  In accordance with New York law, the base salary for this role if filled within New York is $221,000 - $260,000.

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.

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Technology we use

  • Engineering
  • Product
    • JavascriptLanguages
    • PythonLanguages
    • RubyLanguages
    • SqlLanguages
    • D3JSLibraries
    • jQueryLibraries
    • ReactLibraries
    • ReduxLibraries
    • DjangoFrameworks
    • HadoopFrameworks
    • Node.jsFrameworks
    • Ruby on RailsFrameworks
    • SparkFrameworks
    • MongoDBDatabases
    • MySQLDatabases
    • PostgreSQLDatabases
    • RedisDatabases
    • Google AnalyticsAnalytics
    • JIRAManagement

An Insider's view of Checkr

What’s the vibe like in the office?

After 5 years of working at Checkr, I'm pleased to say that the vibe in the office hasn't changed! It's still a fun, vibrant and progressive environment where I'm constantly learning. If you're energized by smart, humble and ambitious professionals, you'll love Checkr.

Ashley DiRuggiero

Human Resources

How does the company support your career growth?

Checkr has helped me grow in my career with challenging Objectives and Key Results (OKRs) each quarter. Because my individual OKRs are aligned with company-wide stretch goals, achieving them means that I am an integral part of moving the company forward AND getting new experiences under my belt!

Temi Vasco


How do your team's ideas influence the company's direction?

The sales team is on the front line with customers which gives us strong customer insights and a tremendous opportunity to shape the product strategy of the company. We bring that feedback to the executive team on a regular basis to influence the company's GTM strategy.

Kristen Faris

VP, Industry Strategy

What are Checkr Perks + Benefits

Checkr Benefits Overview

Checkr provides generous benefits and perks including comprehensive healthcare, unlimited PTO, commuter benefits, gym reimbursement, work from home Wednesday and an annual learning and development allowance.

Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Open door policy
Team owned deliverables
Team based strategic planning
Open office floor plan
Documented equal pay policy
Dedicated Diversity/Inclusion Staff
Highly diverse management team
Unconscious bias training
Mean gender pay gap below 10%
Diversity Employee Resource Groups
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Team workouts
Mental Health Benefits
Retirement & Stock Options Benefits
Company Equity
Checkr offers equity in the form of Restricted Stock Units (RSUs) that vest over a 4 year period.
Performance Bonus
Child Care & Parental Leave Benefits
Generous Parental Leave
We provide up to 12 weeks of parental leave for the primary or secondary caretaker.
Flexible Work Schedule
Checkr provides employees with a flexible work schedule that includes flexible start and end times and a company wide initiative to work from home on Wednesdays.
Remote Work Program
Return-to-work program post parental leave
Company sponsored family events
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Checkr pays $100 a month for commuter benefits.
Company Outings
Free Daily Meals
We provide free breakfast on Monday. Employees get free lunch and dinner on Monday, Tuesday, Wednesday, Thursday, Friday.
Game Room
Stocked Kitchen
Checkr has a fully stocked kitchen including unlimited drinks, snacks, coffee and tea.
Some Meals Provided
Happy Hours
Pet Friendly
Fitness Subsidies
Checkr reimburses $50 a month for gym memberships.
Home Office Stipend for Remote Employees
Professional Development Benefits
Job Training & Conferences
Checkr has a $2,850 budget per person for additional learning and development.
Tuition Reimbursement
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Continuing Education stipend
Online course subscriptions available
Customized development tracks
Paid industry certifications

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