VP of Sales at UpCounsel

VP of Sales

We’re looking for a Vice President of Sales to lead our growing sales organization. The ideal candidate is passionate about scaling a sales organization and the UpCounsel vision. We’re looking for an inspiring leader who can create a performance-driven culture, build a repeatable sales process to deliver results, and coach all levels of sales professionals to develop in their careers.

In this role, you’ll start with a team of 3+ Account Executives, and be expected to scale your team to 10+ AEs within 12 months. Furthermore, you’ll be a part of UpCounsel’s leadership team as we transform the legal industry.

At UpCounsel you will:

  • Recruit, hire, and manage a growing team of experienced Account Executives and managers
  • Build repeatable training processes that help AE’s learn sales skills, product and industry knowledge, and professional habits they need to succeed in the role.
  • Train and assist sales reps in closing complex transactions by teaching best practices in prospecting, managing and closing opportunities, and the skills needed to position UpCounsel as an industry leader.
  • Manage daily and weekly activities, pipelines, forecasts and closed deals to ensure above-quota results based on successful pipeline management
  • Build, measure, and optimize a repeatable sales process to successfully achieve the targeted sales objectives.
  • Create a team culture that’s positive, motivating, and performance-driven.

The ideal candidate will have:

  • You have deep knowledge of a complex sales process preferably with 6+ years of sales management experience in a B2B environment.
  • You have deep knowledge of selling to Mid-Market and Enterprise buyers of ACVs of $50k to $1M.
  • You’ve closed business so you can train AEs on how to be successful in the role
  • You have great people skills. You’ve shown the ability to recruit, hire, and manage talented people.
  • You’re able to build scalable processes, and you have the analytical skills to optimize them over time.
  • You’re curious, constantly learning, and adaptable.
  • You have infectious energy and inspire the people around you.
  • You’re a proven coach: you’ve helped your people unlock their full potential.


  • Experience selling to general counsels and legal teams
  • Experience leading a team selling to general counsels

Perks & Benefits

Health + Vision + Dental Insurance

Full medical, dental and vision to keep you healthy

Competitive salary + equity

Competitive salary & generous stock option package


We encourage our team to be thinking about their future

Open vacation policy

We don’t track PTO - take the time that you need

Enjoy delicious meals

Enjoy lunch at the office

Flexible work hours

Flex your schedule to start and end work when is best for you

Commuter reimbursements

Get reimbursed for your public transportation costs each month

Customize your workstation

Build your workstation and desk to make it comfortable

Team Retreats

Quarterly off-site team retreats full of fun surprises and team inspiration


When it comes to games, we know how to have fun! Foosball, Xbox, fantasy football, and more!

Great coffee 24/7

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