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


Director, Services at Skilljar
Seattle, WA, US

Skilljar is seeking a versatile and proven Director to lead our Services team, which includes management of Skilljar's existing implementation team and building of a professional services team to support both the initial and ongoing Services needs of our customers! This critical function is part of our rapidly growing Customer Success team. This position provides the opportunity to lead customer implementation within a company that is passionate about enabling customers to create a world-class customer experience.

We're looking for an experienced leader who can think and act strategically but also enjoys diving into the details. You will use your expertise building services methodologies and processes to scale as we expand in 2021 and beyond. This is an exciting opportunity to define and drive Services strategy at a rapidly accelerating startup that has dozens of Fortune 1000 and mid-market clients on its roster.


  • Build and lead a world class and rapidly growing Services organization.
  • Own all aspects of Services strategy to include developing and refining service offerings, packaging, pricing as well as hiring, team development, implementation methodology, and project success for the Services team.
  • Develop and implement professional services strategy.
  • Collaboration with cross-functional Sales, Marketing, Product, Engineering, Finance, and Customer Success teams to provide data based business insights to direct the Services team on strategic direction and areas for opportunity.
  • Ensure the highest levels of customer satisfaction, product adoption, and renewal, through highly effective implementations and valuable continued engagement.
  • Define operational metrics for Services team, establish system for tracking, create cadence for review with Services team and management.
  • Direct the activities of the team through ongoing oversight of active implementations and Services projects, ensuring we deliver on time, within budget, and with high quality outcomes and customer satisfaction.
  • Provide mentorship and development feedback to Services team members.
  • Ensure our teams follow standard implementation methodology, and find opportunities to improve our methodologies and tools.
  • Maintain feedback loop with Sales and Customer Success to ensure smooth customer handoff.
  • Evaluate and recommend stage-appropriate software and solutions to improve our effectiveness and efficiency.


  • 8+ years of professional services delivery experience within an enterprise SaaS organization.
  • 6+ years of leadership experience.
  • Demonstrated ability to build strategic and operating plans for a Services department for long-term scale to include experience leading services sales activities (proposal generation, SOW creation, selling Services, change orders, and customer negotiations).
  • Deep expertise in project and program management for enterprise software deployments.
  • Proficient knowledge of technical concepts to inform technical Services offerings.
  • Experienced with a wide range of customer accounts, from SMB ($10K ACV) to enterprise ($1M ACV).
  • Strong empathy for customers combined with a passion for revenue and growth.
  • Highly collaborative and able to build strong cross-functional partnerships with Customer Success, Sales, Marketing, Product, and Finance.
  • Highly organized with strong interpersonal and leadership skills.
  • Strong written and verbal communication skills, ability to articulate and sell a vision internally and externally.
  • Strong execution skills and the ability to drive action and accountability.
  • Consistent track record of defining and optimizing processes.
  • Bachelor’s Degree required, Master's Degree preferred.
  • US work authorization and criminal background check are required.

Our Benefits

  • Comprehensive Medical Coverage: Skilljar pays 100% of our employee premiums for medical, dental, vision, disability, and life insurance. (PTO and family leave)
  • Flexible Time Off: We believe in a healthy work/life balance and trust our employees to take the time off they need to bring their A-game to work.
  • Benefits Package: Skilljar employees receive a monthly technology reimbursement for remote work, 401K savings plan, stock options, and access to an Employee Assistance Program.
  • Inclusive Culture: We are intentional about creating a culture that is fun and inclusive. Join us for Fun Committee events, trivia nights, Bingo, and more!

The Company

Backed by prominent financial institutions, including Mayfield, Shasta Ventures, Trilogy Equity Partners, and Insight Partners, Skilljar is the leading enterprise customer training platform, transforming the way organizations onboard, engage, and retain their customers. Trusted by leading global companies like Slack, Tableau, Liberty Mutual, Cisco, Verizon, and U-Haul, Skilljar provides the essential tools and foundation for successful customer and partner engagement and enablement.

We are a team of bright, dedicated Skillets with startup drive and a passion for education. Headquartered in Seattle, WA, Skilljar is currently operating remotely, with employees based in Washington, Oregon, California, Colorado, Arizona, and Florida.

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.