<link id='css--app'rel="stylesheet" href="/dist/css/app.min.css"> Opportunities – Trilogy


Director, People at Skilljar
Seattle, WA, US

Skilljar is seeking a Director of People Operations to own all things related to our “Skillets,” including talent acquisition, employee experience, engagement, retention, career development, workforce planning, and operational HR systems. This visionary, data-driven, and results-oriented business partner will report directly to the CEO to architect and support our team’s exciting high-growth trajectory.

The Director of People Operations will be both strategic and hands-on in providing support to all of our team members and leadership team. The Director of People Operations will design, define and drive our people roadmap across all talent programs including acquisition, onboarding, employee relations, employee success, learning, performance management, and compensation. The successful candidate will have the ability to help scale our high-performing culture, combined with empathy and inclusion, to ensure that Skilljar is able to attract and hire the right people as we grow our product and service, year over year. This is a hands-on role that requires identifying, building, and developing operational capabilities in a high-growth setting with a small team. 

We’re looking for a passionate, self-starter who succeeds and thrives in a dynamic environment. You are highly-collaborative, able to flex to organizational needs and adjust accordingly.  This is a great opportunity to join a fast-growing company with hundreds of Fortune 1000 and mid-market clients on its roster.


  • Vision and Strategy: Collaborate with our team and leadership to define and drive our People Roadmap to help us best achieve our short and long term business goals. Forsee scaling challenges, drive organizational design, and manage change initiatives to create and maintain a high-performing and collaborative team.
  • Values and Culture: Ensure our core values are evident in all decisions, programs, processes and are aligned with our mission, culture and core beliefs as we grow.
  • Full Lifecycle Recruiting Leadership: Manage Skilljar’s talent acquisition strategy and recruiting process to address both short 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.
  • Employer Brand: In partnership with Marketing, design employment branding initiatives that increase brand awareness. Continue to develop and extend our employer brand through online and offline activities. 
  • Resource Planning: Regularly assess, develop, and implement recruiting programs and technologies, including both traditional and innovative approaches. Monitor and actively manage the budget and recruiting investments.
  • Team Building: Directly lead and grow our People Ops team. Partner with management and leadership to recruit top talent. Understand and anticipate hiring and development needs in a high-growth environment; partner with Finance to prepare updated workforce plans and forecasts that support overall business goals.
  • Operations: Manage effective People Operations, 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.
  • 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 practices. 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.
  • Leadership and Team Development: Partner with CEO and Leadership team to drive leadership development and effectiveness, ensure executive alignment and drive performance aligned with business strategy. Develop programs that prepare high-potential employees through succession planning readiness. Act as a trusted resource for employees, management and leadership on all People related matters.


  • 10+ years of progressive People Operations (Human Resources/Talent) experience
  • 5+ years leading People/HR/Talent teams in high growth tech startup companies.
  • Highly confident using data and systems to represent People Ops and make informed decisions.
  • Demonstrated results in building strong, effective teams at a high-growth startup.
  • Up-to-speed on modern and innovative People Ops practices at fast-growing startups.
  • 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 a recruiting experience that delight candidates and can negotiate/close deals in a highly competitive talent market.
  • In-depth understanding of HR best practices, compliance, and employment law at federal and state levels. Multi-site and remote worker experience is required; global experience strongly preferred.
  • Experience developing and managing effective incentive compensation, benefits, reward and recognition programs where equity is a significant component.
  • Proven success developing talent management functions such as diversity and inclusion, learning and development, succession planning, team engagement, team retention, and performance management.
  •  Exceptional skills at being a trusted partner/coach to managers and leaders across the organization. 
  • Strong conflict resolution and performance management and coaching skills. 
  • Bachelor’s degree required, Master’s degree preferred.
  • 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.