Head of Engineering & Product

Automattic | Friday, June 26, 2020




About this job

Location options: Remote
Job type: Full-time


ruby-on-rails, php, wordpress

Job description


We're looking for a business-savvy technology executive to lead our products and engineering team to produce high quality, innovative, and scalable B2B solutions in alignment with our business goals.

As the Head of Engineering you will serve as an inspirational, forward-thinking, and people-centric leader to define and deliver our technical roadmap, product vision, and strategy for scalability. Your ability to drive technical initiatives, collaborate with peers, and embrace company culture is crucial to the success of this role. Our ideal candidate has pragmatic decision-making abilities, and an unshakable focus on strategy, execution, and delivery. This position will tackle technical challenges, execute large-scale transformation, and develop & grow high performing technology teams. 

Reporting to the CEO and part of the leadership team, you will also act as a strategic business and technology liaison with other divisions of Automattic to help drive decisions that impact the current and future operations of Pressable.


Build a team that will design and deploy truly innovative cloud-solutions that are wide-ranging in scope and high-impact upon delivery. We drive continuous advancements and improvements through our product strategy, business proposition and technical direction. We seek new ways to deliver comprehensive managed WordPress hosting plans to customers, while improving the reliability, scalability, and performance of our Platform.


  • Lead, manage and mentor a team of Engineers, Product Managers, Designers and Related Personnel
  • Plan, build, and develop products (from idea to deployment) that enhance our current offerings.
  • Own the product roadmap & product lifecycle management from concept to launch across all product lines
  • Owning and managing budget responsibilities for technical operations.
  • Lead develop and execute technology strategies and roadmaps to deliver robust, flexible and scalable platforms that meet the needs of our growing company and product evolution.
  • Plan infrastructure and operations investments that scale with the changing needs of the business and communicating all updates to leadership and other relevant team members.
  • Partner with Customer Success and Marketing to assess product/feature usage and success.
  • Drive innovative ideas, solutions, and products through leadership.
  • Establishing a people-first culture with continuous learning that is supported by professional development opportunities, including mentoring and well-defined career paths.

Skills & requirements


  • 10+ years of proven technical leadership delivering B2B solutions with a minimum of 5 years leading a Engineering and  Product teams.
  • Experience leading teams of 10+ people including distributed teams with a proven ability to gain the respect of an existing team of developers.
  • 10+ years hands-on software engineering/development experience building scalable, high-performing cross-platform SaaS solutions 
  • Proven track record of successfully driving growth and scaling new products.
  • Expert knowledge of the product development lifecycle.
  • Strong desire and ability to lead, manage, and nurture talent.
  • Highly proficient in JIRA and other project management tools.
  • Ability to delegate efficiently and create timelines for the development and deployment of all product features
  • Significant experience working in an Agile development organization and possessing the capability to lead others to mature this methodology across a growing organization.
  • Strong executive presence with a proven understanding of all aspects of the business including the ability to create and implement technical strategies, budgets & timeframes that align with both current and future business needs.
  • Demonstrated experience in vendor evaluation and contract negotiation.


  • Outstanding Verbal and Written communication skills.
  • Ability to communicate software product features, technical designs, and product strategy effectively to both technical and non-technical teams.
  • Experience taking a leading role in building high-availability software systems
  • High attention to detail and experience leading multiple, contending priorities simultaneously.
  • History of teamwork and willingness to roll up one's sleeves to push things over the finish line!

Related jobs (6)

Similar job categories (11)