Regional Vice President Sales, Mid-Market

| Seattle
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Skilljar is seeking an additional sales leader for our Account Executive team, focusing on Mid-Market accounts. As a Regional Vice President, you will be primarily responsible for leading a front-line sales team to meet and/or exceed monthly, quarterly, and annual revenue targets.

Skilljar's Mid-Market growth engine is our fastest-growing opportunity, where we are leading the market with our highly proven product and enviable customer testimonials (check out our case studies and G2 reviews!). Customer Education is quickly becoming THE scale engine of Customer Success as companies look to drive product adoption, faster time to value, and net revenue retention.

We’re looking for a motivated self-starter who loves wearing multiple hats and thrives in a high-growth environment. You must be innovative, highly collaborative, and able to think on your feet. This is a phenomenal opportunity to join a rapidly accelerating growth-stage startup that already has hundreds of outstanding Fortune 1000 and Mid-Market clients on its roster. Come join us as we deliver business outcomes for our customers and help millions of people gain job-relevant skills in a rapidly changing economy!

  • Reviewing and advancing your team's opportunity pipeline to deliver the revenue plan.
  • Running the weekly, monthly, quarterly, rhythm of your sales team including pipeline management, deal reviews, and forecasting.
  • Recruiting, evaluating, and motivating a successful team of Account Executives. Activities include joining calls, coaching on deal strategies, and reviewing performance.
  • Building a metrics-based, scalable, ethical, and winning culture for a distributed sales organization.
  • Collaborating with the Sales leadership team and shared revenue functions (Sales Development, Enablement, Revenue Operations, Sales Engineering) to prioritize and set goals that drive business for Skilljar.
  • Partnering cross-functionally with the founders, Marketing, Product, Customer Success, and Finance to win deals and provide input into our overall company roadmap.
  • Supporting the business planning process, including development of go-to-market approaches and territory/comp/quota planning.
The ideal candidate will have:
  • 5+ years experience in B2B software sales, including at least 2 years experience managing an AE team and meeting/exceeding individual and team goals.
  • Demonstrated ability to approach Mid-Market and/or small Enterprise accounts with a value-based solution sale that is evaluated by a buying committee. Ability to quarterback contract and legal discussions. Experienced selling in an emerging category with both new installs and replacements.
  • Metrics and process-driven sales leadership skills. You build confidence with your team by using disciplined sales methodology and a regular cadence of inspection and support to drive outcomes, behavior, and activity. Challenger/MEDDPICC/Selling through Curiosity experience preferred.
  • Entrepreneurial mentality with success and resilience in competitive and dynamic market environments. Able to test and iterate using data. High growth startup experience preferred.
  • Confident, professional, and effective communicator (both verbally and in written form) in a remote environment - both internally and with customers.
  • A belief in Customer Success and the role of Customer Education in driving company performance, successful product usage, and ultimately closing the global skills gap.
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.
  • Benefits Package: Skilljar employees receive a monthly technology reimbursement for remote work, a 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!

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation.

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, Utah, Idaho, Texas, Arizona, Georgia, North Carolina 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.

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Technology we use

  • Engineering
  • Sales & Marketing
    • PythonLanguages
    • Twitter BootstrapLibraries
    • DjangoFrameworks
    • Vue.jsFrameworks
    • PostgreSQLDatabases
    • WordpressCMS
    • SalesforceCRM


Headquartered in Seattle, WA, Skilljar is currently operating remotely, with employees based all over the US.

An Insider's view of Skilljar

How would you describe the company’s work-life balance?

Even though Work and Life are often happening in the same room these days, Skilljar encourages everyone to create a daily ritual that signals a "Start" and "Stop" to the workday. Whether it's simply shutting down your laptop, taking an end-of-day stroll, or brewing a cup of tea to wrap up the day; the team supports creating a balance.


Digital Marketing Specialist

What projects are you most excited about?

I’m most excited about evolving our platform from Heroku onto AWS and giving us more control over our app (and cost savings).

We get to tackle the challenges of deploying software (build, test, deploy, monitor, etc.), and it’s a cool (and challenging) opportunity to introduce fundamental changes in our infra while continuing to support our devs.


DevOps Engineer

How does the company support your career growth?

The biggest way that Skilljar supports my career growth is in providing me with the flexibility and trust to take on new projects. My managers and the leadership team give me a lot of control over my job and how I want to grow. I have learned and grown more in my short time here than I have been able to in the last few years in my previous roles.



What's the biggest problem your team is solving?

The biggest problem my team is solving is how to scale the company. We have a solid foundation already. However, as we grow, we're choosing systems and processes to position us for growth. It is challenging and exciting to be a part of this process. It's rewarding to see our impact on other teams and the long-term benefit to the whole company.


Financial Analyst

What are Skilljar Perks + Benefits

Skilljar Benefits Overview

At Skilljar, we value our employees' wellness. As a result, we strive to provide a great set of benefits. Skilljar pays 100% of our employee premiums for medical, dental, vision, disability, and life insurance! We also cover 50% of premiums for dependents you add to our plans.

Our extensive perks and benefits include:
Long and short-term disability
Life insurance
Flexible Time Off
401(k) Retirement Savings
Employee stock options
Employee Assistance Program (EAP)
Great events - virtual company and team events, happy hours, trivia/game nights, and more!

Intracompany committees
We have a volunteer-based fun committee. They have a budget side aside that they use to help through quarterly events for the entire company.
Daily sync
Team owned deliverables
Group brainstorming sessions
Unconscious bias training
Health Insurance & Wellness Benefits
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Retirement & Stock Options Benefits
Company Equity
Child Care & Parental Leave Benefits
Flexible Work Schedule
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Company Outings
Some Meals Provided
Happy Hours
Professional Development Benefits
Lunch and learns
Company catered lunch and employee-led, weekly lunch and learn meetings

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