Vice President of Customer Expansion

WordPress VIP (WPVIP), the enterprise division of Automattic, is the world’s leading agile content management platform. Our goal is to bring the ease and agility of WordPress to the world’s largest companies. We work with customers like Salesforce, Facebook, CNN, Slack, Time, Capgemini and hundreds more to empower their teams to produce digital content faster and smarter, while also ensuring premium security and scalability. 

About the Role:

We’re looking for an experienced leader to build and scale our Relationship Management and Expansion Sales organization. In this role, you’ll work directly with VIP’s Chief Revenue Officer to develop strategy around growing Net Revenue Retention as well as Gross Revenue Retention. You’ll be responsible for building and leading multiple teams of Relationship Managers and Strategic Sales Executives who manage accounts across various product lines and customer segments.

This isn’t your typical work-from-home job — we are a fully-remote company with unlimited paid time off. To see a full list of benefits by country, check out our Benefits Page. Check out these links to learn more about How We Hire and What We Expect from Ourselves.


  • Develop strategy around improving GRR and NRR through VIP’s Relationship Management and Expansion Sales teams for our expanding portfolio of products 
  • Develop a staffing plan and build a team to support this strategy, including hiring, mentoring, and otherwise developing a high-performing team
  • Establish operational metrics for the team
  • Develop playbooks to increase revenue in existing accounts through cross-sell and upsell
  • Aid in building additional sales capabilities to sell products and offerings from within the Automattic portfolio, or from direct acquisitions 
  • Work closely with Product Marketing to develop and facilitate collateral and lifecycle marketing for customers
  • Work with our Sales and Customer Success Operations team to define and optimize our customer lifecycle
  • Align with the finance and sales team around retention and expansion planning and forecasting
  • Collaborate closely with our onboarding, support, professional services, and engineering teams to ensure we are driving customer value 


  • Experience as a VP or Senior Director of Sales for a high scale SaaS platform with a history of product integrations
  • Proven success building and leading high performing relationship management and sales teams to meet GRR and NRR goals
  • Demonstrated ability to create and develop staffing plans (including hiring, development, and succession planning)
  • Ability to work North American hours (UTC-5 to UTC-8) and coordinate with a distributed global team

About Automattic

We are the people behind, WooCommerce, Tumblr, Simplenote, JetpackLongreads, Day One, PocketCasts, and more. We believe in making the web a better place.

We’re a distributed company with more than 2000 Automatticians in 96 countries speaking 120+ different languages. We democratize publishing and commerce so anyone with a story can tell it, and anyone with a product can sell it, regardless of income, gender, politics, language, or country.

We believe in Open Source and the vast majority of our work is available under the GPL.

Diversity, Equity, and Inclusion at Automattic

We’re improving diversity, equity, and inclusion 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 DEI 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 DEI People Lab series for further learning. Diversity, Equity 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. Learn more about our dedication to diversity, equity, and inclusion and our Employee Resource Groups.

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All Jobs Require

  • Great communication skills. We’re a distributed team, so frequent and clear written communication is a must.
  • Self-driven work ethic. You need to be a self-starter who loves taking initiative and seeing things through to completion.
  • Curiosity and the desire to learn. Our business is changing and growing fast, who knows what will be the skills of tomorrow? Flexibility is key.
  • Ability to Travel. We value those rare occasions when we meet our colleagues in person. Normally, we require 2–3 non-consecutive weeks of travel per year, usually by plane. Currently, company travel is limited, and travellers must be vaccinated. All travel is optional for now. We’re continuing to explore new, remote ways to stay connected.