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


Director, Sales Development at Skilljar
Seattle, WA, US

Skilljar is seeking an experienced candidate to lead our Sales Development team (currently all virtual) and drive pipeline creation efforts. The successful candidate will lead by example - measuring, monitoring, and holding reps accountable for their daily activities, results, and professional development, while consistently achieving their own goals. They will work closely with the Account Executive team, collaborate heavily with demand gen and marketing, and partner with other various executives to increase efficiencies and improve SDR processes and systems, all while guiding a strong, cohesive, and collaborative team.

We’re looking for a motivated, process-oriented self-starter who is comfortable wearing multiple hats and thrives in a dynamic environment. You must be nimble, highly-collaborative, and able to think on your feet. This is a great opportunity to join a rapidly accelerating growth-stage startup that has hundreds of Fortune 1000 and mid-market clients on its roster.


  • Train and optimize a team of reps responsible for developing inbound and outbound sales pipeline across multiple customer segments and territories. Successful reps are promoted to full-cycle or closing sales positions within two years, making hiring and training a particularly important function.
  • Establish metrics and help the team improve by understanding their performance on a daily basis. Detail-oriented, process driven, roll-up sleeves-type leader who will build confidence and competence amongst the team by using disciplined sales methodology, metrics-based management, and a regular cadence of inspection and support to drive activity, behavior and outcomes.
  • Coach, develop, and mentor a combination of first time and experienced front line SDR managers to hire, develop and retain world-class SDR talent.
  • Manage outside vendors and service providers related to the sales development function.
  • Refine the sales pitch and process to achieve target results for qualified opportunity generation. Provide daily, side-by-side coaching and call monitoring.
  • Partner with Finance to compile weekly/monthly team reports, proactively working to improve the cadence and throughput of sales development resources.
  • Partner with Marketing to manage the inbound lead flow and track the efficiency of sales and marketing programs.
  • Partner with Revenue Operations to oversee usage of team systems including HubSpot, Outreach, ZoomInfo, LinkedIn Sales Navigator, and more.
  • Work closely with Sales and Marketing leadership to ensure the success of marketing campaigns in driving net new pipeline and revenue.
  • Help create a fun, high energy environment - even in a virtual world!


  • 10+ years of B2B Sales, Sales Development, or Inside Sales experience, preferably in enterprise SaaS.
  • 5+ years of managing sales development teams, with proven success as a manager (recruiting, training, performance management) in a fast-growth environment
  • Able to build a scalable, sustainable, winning culture for remote, phone and email-based, outbound sales and account teams, with activity based management, hands on-coaching, and high energy/team work ethic.
  • A solid understanding of metrics related to top of the funnel and pipeline dynamics in Commercial and Enterprise B2B buying cycles. Understands the different methods of targeted demand generation/ABX and has demonstrated the ability to use them effectively.
  • Proven ability to ramp sales reps over time in a systematic way - development of a training program focused on product, process & selling skills.
  • Experience selling into mid-market B2B companies strongly preferred (5 or 6 digit annual contracts, consultative solution selling through stakeholder committees).
  • Excellent working knowledge of inbound & outbound prospecting technologies, tools, and managed services vendors.
  • An ability to interact effectively with all levels of management and with multiple departments including sales, marketing, product marketing, and finance.
  • Ability to handle ambiguity and change - high growth startup experience strongly preferred.
  • Excellent verbal and written communication skills.
  • 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 the leading enterprise customer training platform, transforming the way organizations onboard, engage, and retain their customers. Trusted by leading global companies like Zillow, 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, and Colorado.