Head of Engineering & Product, Pressable


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.

Pressable is a new breed of technology company: one-part WordPress managed Hosting and one-part services innovation empowering small agencies to giant clients to scale their business on the WordPress platform. Pressable’ s platform enhances WordPress with developer tools, cloud management, security, and analytics, so that companies can build and deploy their digital experiences faster than ever.

Pressable is owned by Automattic, Inc the brand behind Wordpress.com, WooCommerce, Jetpack, Crowdsignal, WordPress VIP and many others.  Founded in 2010, Pressable follows Automattic’s distributed team model with employees all over the world.  We engage the most brilliant minds regardless of location and give them the best resources to perform the finest work of their careers. 


As the Head of Engineering & Product 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. 


  • 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!


We’re improving diversity in the tech industry. At Automattic, we want people to love their work and show respect and empathy to all. We welcome differences and strive to increase participation from traditionally underrepresented groups. Our D&I committee involves Automatticians across the company and drives grassroots change. For example, this group has helped facilitate private online spaces for affiliated Automatticians to gather and helps run a monthly D&I People Lab series for further learning. Diversity and Inclusion is a priority at Automattic, though our dedication influences far more than just Automatticians: We make our products freely available and translate our products into and offer customer support in numerous languages. We require unconscious bias training for our hiring teams and ensure our products are accessible across different bandwidths and devices. Read more about our dedication to diversity and inclusion.


  • Health Benefits (100% Paid Employee Medical, Dental, and Vision)
  • Matching 401(k)
  • Life Insurance
  • Work from home
  • Open vacation policy (no set number of days per year).
  • Home office setup
  • Hardware and software, books or conferences that promote continued learning
  • Open parental leave