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General Manager

Pressable intends to hire a new General Manager. If you have 10+ years of progressive leadership experience building and managing a B2B SaaS product, consider applying.
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About the Company

Pressable is a WordPress hosting and digital experience platform. We were founded in 2010 with one goal in mind: to empower site owners to focus on building their sites instead of dealing with technical issues. We accomplished this by providing world-class managed WordPress hosting, fast/reliable servers, and an easy to use panel that tied it all together, all backed by five-star-rated support. 

The company rebranded in 2013 and began working more closely with developers, agencies, and ecommerce site owners. 

Following the acquisition by Automattic (the parent company of, WooCommerce, Tumblr and others), the architecture behind Pressable was rebuilt from the ground up, resulting in industry accolades for speed, reliability, and service. 

Now, a once small South Texas tech company has become a worldwide hosting platform that serves startups and Fortune 1000 companies alike. But one thing hasn’t changed from our humble roots: the goal to provide world-class managed WordPress hosting backed by award-winning customer support.


Pressable was founded with the mantra “Focus on your content, not your content management system”. 

As a distributed company, we all work from the location of our choice. We care about the work we produce, not just the hours we put in.

Our platform improves WordPress with developer tools, cloud management, security, and analytics, so that companies can build and deploy their digital experiences faster than ever. 

Team members are curious, driven, compassionate, tenacious, autonomous, friendly, independent, collaborative, communicative, supportive, self-motivated, and amazing with .gifs!

Come work with people interested in making the web and the world a better place!

What you’ll do:

The Pressable GM reports to Automattic’s Head of Other Bets, Sonal Gupta, and to the Pressable board.

In this critical leadership role, you will lead all strategic, product, and operational decisions for Pressable. You will be the company champion and GTM visionary for all current and future products with the goal to delight users and offer world class experiences for our customers.

Key focus areas:

Leadership and Team Cultivation

  • Communicate upward (Automattic), inward (Executive Team and team members), and outward (Industry Partners and Customers) to create alignment around shared goals.
  • Build strong teams within each department, utilizing Automattic’s expertise and best practices in distributed work. 
  • Empower and retain talent by cultivating an outstanding culture.
  • Set clear, achievable goals for yourself and your team.
  • Understand where to outsource talent vs bringing in-house.
  • Build cross functional teams capable of overcoming communication, location, and organizational challenges.

Business Planning / Analytics

  • Forecast needs and manage cash flow requirements.
  • Maintain tight control over spending ensuring adherence to budget.
  • Deliver monthly, quarterly, and annual reports on financial performance to the Pressable Board.
  • Maintain healthy and predictable growth by establishing and consistently meeting execution milestones related to the company’s financial and operating plans.
  • Continuously monitor performance and iterate to improve outcomes across: product development, pricing, customer acquisition/retention, and future strategies.

Product Development

  • Collaborate with key internal partners to define, refine, and improve the product vision, value proposition, and product roadmap, with a focus on growing user acquisition, retention and engagement.
  • Develop effective, informative feedback loops.
  • Translate data and innovate upon features and functionality.
  • Implement tools to prioritize and optimize workflows.

Marketing / Sales / Customer Support

  • Align sales, marketing, and product/tech teams to define differentiated offerings.
  • Work with the sales team to execute on near- and long-term sales plans, with the ultimate goal of building a data-driven and predictable revenue stream. 
  • Define ideal customers and market segments using quantitative insights.
  • Oversee marketing programs using content and experiences to build, attract, engage and convert, generating demand with target customer segments and partners.
  • Establish and maintain brand touchpoints – including websites, social channels and marketplace outposts – to engage customers across segments.
  • Maintain a customer service department capable of fast response to arising customer needs. 

This position may be a good fit if you have:

  • 10+ years of progressive leadership experience building and managing a B2B SaaS product.
  • 5+ years leading high performance teams, preferably across multiple departments and through periods of high growth.
  • Experience communicating with high level executives and/or Board members.
  • Experience working across time zones and complex corporate layers to navigate boundaries and keep your team progressing.
  • Experience presenting to a board or leadership team to drive consensus for your strategy while owning the results.
  • Experience taking strategy and bringing it to life through coordinated action across all departments of an organization, regardless of team location.
  • An innovative and forward-thinking mindset with strong market and product instincts.

What you’ll bring:

  • A commitment to continuously surpassing the customers’ expectations in every way.
  • Excellent written communication across various digital channels such as email, messaging apps, and shared workspace tools.
  • An entrepreneurial spirit with a high level of energy and dedication, and an unrelenting drive to succeed and win.
  • An exceptional ability to identify and break down problems to find unique solutions and remove single points of failure.
  • Proven hands-on leadership, not just managerial experience.
  • The ability to take ownership of decisions while involving others in the decision-making process.
  • A dedication to learn and educate team members across the company.
  • Empathy and honesty; you keep your word, care about fellow teammates, and do what’s right.
  • Comfortability with constant change and curiosity about tomorrow.


As an Automattic subsidiary, we’re serious about growing diversity in the tech industry, nurturing an environment where people love their work and show respect and empathy to those with whom they interact. We welcome our differences and strive to increase the visibility of traditionally underrepresented groups. Learn more about Automattic’s dedication to diversity and inclusion and our Employee Resource Groups.


Does this sound interesting? If yes fill out our application form below. In your cover letter, let us know what you can contribute to Pressable. 

Want to increase your chances of standing out? If so, please include answers to the following in your cover letter:

  • Tell us about a time when you were able to build consensus while navigating different viewpoints or perspectives.
  • Tell us about your experience leading remote teams.
  • Describe your leadership style.

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