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Director, People

| Seattle
Skilljar is seeking a Director, People to lead our recruiting, people operations (HR), and employee engagement strategies in support of our company’s rapid growth. This role will report directly to the CEO and is a critical role to help ensure Skilljar is able to attract, hire, and retain the right people (Skillets) to continue scaling our product, service, and organization year over year. This visionary, data-driven, and results-oriented business partner will architect and support our team’s exciting high-growth trajectory.
In partnership with the Skilljar leadership team, you will be responsible for optimizing the talent acquisition structure and processes utilizing Skilljar’s talent philosophy. You will help build a unique employer brand and lead a Recruiting team to deliver outstanding candidate experiences while hiring and retaining best-in-class talent. In addition, you’ll own employee experience, engagement, retention, career development, workforce planning, and operational HR systems.
Our talent philosophy:
- Recruiting is vital to Skilljar’s success and is everyone’s job.
- We succeed by creating the best candidate experience possible.
- The cost of a mis-hire far exceeds the cost of an empty seat.
- Past performance and project assessments are the best indicators of future success.
- Skilljar fit is a combination of functional skills and alignment with our core values.
- Talent acquisition and retention are data-driven disciplines.
- We all have unconscious biases that should be factored into our interview process.
You must be very comfortable wearing multiple hats in a highly ambiguous environment, building and iterating on processes on the fly, and working closely with cross-functional teams. This is a fantastic opportunity for a driven and focused leader to get in on the ground floor of a rapidly accelerating startup that has already delighted dozens of Fortune 1000 and mid-market clients.


  • People Vision and Strategy: Collaborate with our team to define and drive our People Roadmap to help us best achieve our short and long term business goals. Anticipate scaling challenges and manage change initiatives to help create a high-performing, flexible, collaborative, and innovative team. Help maintain our core values and ensure that all decisions, programs, and processes are aligned with our culture and core beliefs as we grow.
  • Full Lifecycle Recruiting Leadership: Drive Skilljar’s talent acquisition strategy and recruiting procedures to address both short-term and long-term talent needs. Develop and execute best-in-class practices for end-to-end candidate experience - inclusive of sourcing, screening, interviewing, and hiring - with an emphasis on outbound sales recruiting.
  • Reporting: Establish, track and iterate on internal and external measurements focusing on the effectiveness of the Talent function, including recruiting KPIs such as cycle time, channel, funnel, and ROI metrics, as well as HR metrics such as retention, engagement, and diversity.
  • People Operations: Manage effective People Operations and systems, including quarterly metrics reporting, HR systems administration, compensation, leaves of absence, benefits, immigration, remote worker policies, new hire orientation and onboarding, new hire surveys, semi-annual employee surveys, quarterly check-ins, and exit interviews. Ensure compliance with employment regulations at federal and state levels, leveraging outside counsel when necessary.
  • Recruiting Process: Work with Recruiters to continually enhance hiring processes and helping to improve our ability to attract and properly vet the right candidates. Assist recruiters and hiring managers in making final selection decisions. Train hiring managers and interviewers on Skilljar’s interview process and industry best practices.
  • Business Partner: Partner with leadership to understand the business needs and support our team in all components of defining talent needs both current and future. Regularly assess, develop, and implement recruiting programs and technologies, including both traditional and innovative approaches. Monitor and actively manage the budget and recruiting investments.
  • Performance Management: Provide business partner support for functional leaders to help grow our capabilities, identify high and low performers, develop career plans, and drive employee retention. Design and implement company-wide performance management programs that drive feedback and learning in support of company goals. Coach managers and employees through performance management issues. Act as a trusted resource for employees and management on all People related matters.
  • Employer Brand: Continue to develop and extend our employer brand through online and offline activities.
  • Agency Management: Manage third-party agencies and contractors on a weekly basis to ensure effective, accountable relationships and a financial return on investment.
  • People Management: Coach, mentor, and expand our amazing Talent team to meet our aggressive hiring goals.


  • 8+ years of progressive People/HR/Talent experience, with an emphasis on recruiting and talent acquisition
  • 4+ years leading People/HR/Talent teams
  • Demonstrated results in building strong, effective teams at a high-growth startup is required, enterprise SaaS experience preferred.
  • Up-to-speed on modern and innovative People Ops practices.
  • In-depth understanding of HR best practices, compliance, and employment law at federal and state levels. Multi-site and remote worker experience is required.
  • Excellent skills to communicate and coach effectively at all levels across the full spectrum of seniority. Successful track record of being a partner to managers across a variety of functional areas, as well as the demonstrated capability to interface and maintain effective relationships with all departments and staff.
  • Ability to develop recruiting programs for both local and remote hiring, utilizing a mix of innovative sourcing techniques and tools that attract high-quality, passive candidates.
  • Ability to create an experience that delights candidates and can negotiate/close deals in a highly competitive talent market.
  • Exceptional collaboration, relationship, and consultative skills with success in fostering long term relationships and partnerships with internal teams as well as external partners and candidates.
  • Strong analytical skills and business acumen with the ability to utilize data and metrics to drive decision-making.
  • Excellent organizational and prioritization skills with high attention to detail.
  • US work authorization and criminal background check are required.

The Company
Backed by prominent financial institutions, including Mayfield, Shasta Ventures, and Trilogy Equity Partners, Skilljar is building the Customer Education Platform of choice for mid to large-sized enterprises. Trusted by leading global enterprise organizations like Cisco and Verizon, Skilljar’s SaaS platform empowers Customer Training and Enablement teams to successfully onboard, engage, and retain customers and increase product adoption throughout the customer journey. We are a team of bright, passionate Skillets with Amazon roots and startup drive. Centrally located just a few blocks from Westlake Center in downtown Seattle, the Skilljar office is a fun, perfectly-caffeinated, and creative place to be (come check out our 3-D laser printer). Apply to join us!
Skilljar is an Equal Employment Opportunity (EEO) employer and does not discriminate on the basis of race, color, national origin, religion, gender, age, veteran status, political affiliation, sexual orientation, marital status or disability (in compliance with the Americans with Disabilities Act) with respect to employment opportunities.
Skilljar does not accept nor are we responsible for any fees associated with unsolicited resumes, LinkedIn bios, or any other candidate introductions.

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Technology we use

  • Engineering
    • PythonLanguages
    • Twitter BootstrapLibraries
    • DjangoFrameworks
    • Vue.jsFrameworks
    • PostgreSQLDatabases


Centrally located just a few blocks from Westlake Center in downtown Seattle, the Skilljar office is a fun, perfectly-caffeinated, and creative place!

What are Skilljar Perks + Benefits

Skilljar Benefits Overview

At Skilljar, we value our employees' wellness. As a result, we strive to provide a great set of benefits. Skilljar pays 100% of our employee premiums for medical, dental, vision, disability, and life insurance! We also cover 50% of premiums for dependents you add to our plans.

Our extensive perks and benefits include:
Long and short-term disability
Life insurance
Flexible Time Off
401(k) Retirement Savings
Employee stock options
Discounted ORCA pass, only $20/month
Employee Assistance Program (EAP)
Kitchens stocked with your favorite snacks and drinks
A catered Lunch and Learn each week
Great events - weekly happy hour, summer & winter Parties, trivia/game nights, and more!

Eat lunch together
Daily stand up
Open office floor plan
Health Insurance & Wellness Benefits
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Retirement & Stock Options Benefits
Company Equity
Child Care & Parental Leave Benefits
Flexible Work Schedule
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Stocked Kitchen
Some Meals Provided
Happy Hours
Professional Development Benefits
Job Training & Conferences
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