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


Senior Account Executive, Mid-Market at Skilljar
Illinois, US

Skilljar is helping millions of people around the world gain job-relevant skills in a constantly evolving economy. We’re delivering business outcomes for our customers, innovating in an exciting new category, and driving impact to narrow the global skills gap!

To achieve the mission, we are growing our Mid-Market segment and seeking a Senior Account Executive to join our growing Sales team; reporting to the Regional Vice President, Mid-Market. This person will engage with prospective companies in the high end Mid-Market and low end Enterprise segment to identify how the Skilljar platform can help them to drive key business and growth objectives. As a trusted advisor, you’ll promote Skilljar's solutions and help prospects understand how a customer education platform can allow them to reduce customer churn, increase customer engagement, and grow customer relationships.

We are seeking to hire a motivated sales professional that is comfortable wearing multiple hats and can succeed in a dynamic environment. You must be flexible, highly-collaborative, and able to think on your feet. This is an excellent opportunity to join a rapidly accelerating startup that has dozens of Fortune 1000 and mid-market clients on its roster.


  • Own the end-to-end sales process in order to consistently achieve individual sales quotas and deliver against key performance metrics.
  • Engage and collaborate with appropriate resources such as Solutions Engineers, Professional Services and Customer Success to drive forward opportunities
  • Build and maintain a pipeline of potential sales opportunities.
  • Understand prospect difficulties to develop a value proposition specific to their needs and business goals.
  • Create and deliver customized sales presentations and high-impact demonstrations.
  • Strategically navigate procurement cycles with multi-stakeholder sign-offs, including executives, legal, information security, etc. Develop and negotiate proposals and contracts.


  • 4+ years of demonstrated ability to sell/close B2B SaaS customers.
  • Consistent track record of achieving sales quotas.
  • Ability to focus on new customer acquisition and building personal pipelines.

Additionally, these are preferred qualifications:

  • Consultative sales experience for products/solutions that affect multiple partners and areas of a customer organization.
  • Ability to develop, implement, and complete an inside sales territory strategy with minimal oversight or direction.
  • Comfortability working in a small, self-directed environment with evolving market feedback.
  • Experience with sales methodologies such as MEDDIC and Value Selling.
  • Ability to collaborate on a team and communicate in a clear and thoughtful manner.
  • Demonstrated organization skills, attention to detail, and customer focus.
  • A mix of startup and large company experience is a plus.

Don’t meet every requirement? At Skilljar, we are committed to building a team that embraces a variety of backgrounds, experiences, perspectives, and skills. We believe that the more inclusive we are, the better our work will be. Even if your previous experience doesn’t perfectly match the job qualifications listed, we encourage you to apply.

Skilljar Base Pay Philosophy:

At Skilljar, we strive for salary range transparency in our hiring process. This is a major step towards not only complying with state and local regulations where required, but also to make sure Skilljar is putting pay equity and DEIB top of mind during the hiring process. Base salary is only a part of the total rewards package - this role will also be eligible for a new hire equity grant in the form of stock options, and sales commission. Below is the base salary range for this role:

All Remote US: $125,000 - $137,500

Our Benefits:

  • Comprehensive Medical Coverage: Skilljar pays 100% of our employee premiums for medical, dental, vision, disability, and life insurance. 
  • 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.
  • Paid Parental Leave: For our employees starting or growing their families, Skilljar offers paid parental leave for both birthing and non-birthing parents. 
  • Benefits Package: Skilljar employees receive a monthly technology reimbursement for remote work, 401(k) 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 forward-thinking, dedicated Skillets with startup drive and passion for education. Founded in Seattle, Skilljar is now a fully distributed company that exclusively hires in Washington, Oregon, California, Arizona, Colorado, Utah, Idaho, Illinois, Texas, Georgia, Florida, Missouri, Montana, North Carolina, New York and Virginia.

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.