Director, Sales Enablement, WooCommerce

The Role

WooCommerce is looking for a motivated and dynamic Director of Sales Enablement to help support our fast-growing Sales and Customer success team. You will be responsible for training/ramping our new hires, crafting a best-in-class onboarding & training program, sales collateral, tools, etc.. A successful candidate has experience onboarding, training, and enabling rapidly growing highly successful sales teams. You will ultimately be responsible for growing sales efficiency through reduced time to first deal closed, and overall revenue growth.



  • Develop curriculum, content, and all ongoing training programs including sales/customer success skills training, competitive intelligence, playbooks, and product training.
  • Maintain program and collateral up-to-date alongside a "rapidly developing product and roadmap".
  • Collaborate closely with cross-functional leaders to identify gaps or weaknesses in existing sales processes, build and implement solutions that improve our process and enable salespeople/customer to succeed.
  • Be a thought partner across GTM leadership on short and long-range (multi-year) strategies, including operating priorities, org design, market analysis, and select priority performance improvement programs.
  • Serve as a liaison between sales, customer success, marketing and product teams.
  • Use performance data to identify knowledge or skill gaps across the sales and customer success teams.
  • Lead a professional, hard-working team by providing ongoing mentoring, coaching, and feedback to support efficient performance and development of team members.



  • At least 5+ years of enabling, training, mentor, or leading salespeople.
  • Have experience and proven track record of successfully selling a sophisticated B2B product.
  • Lead and optimize all sales onboarding to improve sales efficiency and reduce new hire ramp time.
  • High degree of proficiency with basic business systems (especially Google Apps, LMS, Zoom, Salesforce).
  • Self-starter and ability to build programs from scratch.
  • Powerful storyteller: written, verbal, and visual.
  • High energy, self-motivated, positive, outgoing, engaging, proactive, and able to relate well to a diverse audience.


About Automattic

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

We’re a distributed company with more than 1800 Automatticians in 90+ countries speaking 90+ 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.