Head of Engineering at UpCounsel

Head of Engineering

UpCounsel is on a mission to make the legal experience remarkable for businesses, and we’re looking for the leaders to drive mission with strong technology and product. We work with thousands of entrepreneurs and thriving companies to deliver high quality, convenient, and cost effective legal services from the world’s largest legal community. When businesses can access great legal services, they make better decisions and can grow their business with confidence. UpCounsel’s product facilitates an end-to-end experience for both businesses and lawyers, which places us firmly at the middle of this untouched, yet critical industry.

As Head of Engineering you’ll own our technology strategy and vision. Reporting to the CTO, you will be the engineering leader on the senior management team and across the organization. You’ll lead a team of talented engineers to architect, build and maintain the product necessary to hit strategic milestones and long term objectives. This role requires someone who has a strong engineering background, proven leadership experience, is extremely organized, data-driven, an outstanding communicator, results-oriented, and thrives on solving hard problems. More importantly, we want you grow our team of talented engineers, and inspire them to drive towards a shared vision.

Required skills:

  • BS or MS degree in computer science, engineering or similar related
  • 10+ years experience as a software engineer
  • 5+ years experience as an engineering manager or team lead
  • Experience with Ruby on Rails, Node.js, Python and others
  • Background in scaling web applications
  • Experienced in deploying and managing DevOps and infrastructure tools for deployment, monitoring and continuous integration with AWS
  • Strong understanding of unit tests, integration tests, TDD
  • Experience building up QA teams and processes to improve quality
  • Experience with scaling SOA and microservices
  • Extensive experience working with both relational and NoSQL databases (MongoDB)
  • Knowledge of ETL processes and data pipelines
  • Strong people management skills and understanding of different leadership styles
  • Exceptional written and verbal communication skills
  • Experience mentoring junior developers and blooming engineering managers
  • Managed large and small engineering teams, experience with successfully scaling teams in the past

At UpCounsel, you will:

  • Define engineering strategy and roadmap in collaboration with the product and executive teams
  • Scale / manage our software engineering teams and shape the evolution of our single engineering team into high performing squads
  • Drive a strong hiring process to identify and hire highly skilled team members
  • Provide direction and mentorship to junior developers and new managers
  • Lead by example: regularly contribute code, review PRs, and maintain a deep understanding of our stack
  • Assist in designing and implementing onboarding sessions to maximize ramp time for new hires
  • Manage and improve upon existing development processes such as code reviews, continuous integration, automated deployments, dev ops, etc
  • Ensure high quality code is shipped each and everyday
  • Minimize critical bugs, downtime and functional failures
  • Work with teams to remove obstacles and support each team member towards success
  • Lead multiple recurring meetings with the engineering team as well as other teams

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

We're serious about getting quality coffee from throughout the world

We're in San Francisco