<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 the 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, and is responsible for working directly with our customers to enable them to successfully implement Skilljar and grow their education programs through Skilljar’s Services offerings to achieve business goals. This position provides the unique opportunity to lead customer implementation within a company that is focused on enabling our customers to achieve a world-class customer onboarding experience.

You must be a hands on leader who can think and act strategically but also enjoys diving into the details. You will leverage your expertise in building services methodologies and processes that scale as we expand in 2020. You must be an experienced leader, mentor, and coach who is able to scale an organization, while guiding team members through the challenges of hyper growth. This is a great opportunity to join 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-driven business insights to inform 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 value-added 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 coaching and development feedback to Services team members.
  • Ensure our teams follow best practice implementation processes, and identify 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 enhance our effectiveness and efficiency.


  • 8+ years of professional services delivery experience within an enterprise SaaS organization.
  • 6+ years of high performing team 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.
  • Proven 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!