At WooCommerce, we’re on a mission to democratize commerce. Millions of merchants around the world build their businesses with our open-source platform—and we’re scaling how we support them. WooCommerce already powers nearly 10% of all websites on the web. It’s instantly available to the WordPress hosting platform, which powers over 40% of the web today.

As one of the fastest growing areas of Automattic, we’re expanding. We’re looking for an experienced Midmarket Account Executive to join our Sales team. This role is critical to building on our momentum with our high value merchants ($1M+ TPV) as well as shaping how we leverage the strengths of our full organization to drive more wins in the field.

If you are a top performer, this is a chance to plug into a product with real market pull and help build and scale a modern sales-led growth motion alongside it. You will work complex deals, win marquee logos, and create expansion playbooks that others will follow. Bring your craft, your curiosity, and your conviction. We will back you with a platform merchants love, a team that plays to win, and the tools to make it happen.

Responsibilities

Own a revenue target for net-new acquisition and expansion across Midmarket and Enterprise merchants with $1M+ TPV.
Successfully manage both transactional deals and larger, more complex opportunities that involve partner products and agency services.
Team-sell with a partner Sales Engineer to co-sell complex solutions, lead discovery, shape requirements, and build compelling value cases that tie to merchant outcomes.
Run the full sales cycle from prospecting to close: discovery, solution mapping, business case, negotiation, and executive alignment.
Build urgency and clear close plans with verifiable next steps, stakeholder maps, and documented mutual action plans.
Maintain accurate sales forecasts and pipeline information, and drive strategic improvement of forecasting processes.
Land and expand. Drive initial wins, then grow accounts through cross-sell and upsell across platform, payments, and partner solutions.
Actively engage in pipeline generation activities, including regular outbound prospecting and partner agency relationship management.
Represent the brand at events, webinars, and partner activities, developing a healthy referral and partner-sourced pipeline.
Collaborate cross-functionally with Product, Marketing, Agency and Technical Partnerships, Customer Success, and Support to remove friction and accelerate time to value.
Translate market feedback into crisp insights for product and leadership, including competitive signals and gaps that block adoption.
Develop and execute innovative, vertical-specific sales strategies that accelerate market penetration.
Contribute to a high-performing sales culture by sharing best practices and mentoring team members. Help refine playbooks, messaging, and tooling as we scale a modern SLG motion alongside our PLG engine.

Requirements

4+ years of B2B quota-carrying experience in Ecommerce, SaaS, or platform sales, with consistent attainment against multi-hundred-thousand or seven-figure annual targets.
Proven success selling to Midmarket or Enterprise clients with complex buying groups, procurement, security, and legal reviews.
Demonstrated outbound prospecting skills, including account research, sequencing, and executive-level outreach that converts to qualified opportunities.
Strong command of consultative and value-based selling, including discovery, economic impact modeling, and business case development.
Experience running structured deal processes with multi-threading, mutual action plans, and disciplined pipeline management.
Strong understanding of enterprise software, IT landscapes, and content management systems.
Comfortable working with executive-level prospects, negotiating terms, and reviewing contracts.
Comfortable in a high-growth, builder environment. You can operate with imperfect data, roll up your sleeves, and still deliver clean execution.
Excellent communication and presentation skills, written and verbal, with the ability to simplify technical concepts for non-technical stakeholders.
High integrity, ownership, and a team mindset. You share wins, ask for help early, and put the merchant outcome first.
Self-motivated with a drive to achieve revenue and growth targets, both individually and as part of the company.

Preferred Qualifications

Experience in ecommerce, payments, fintech, marketplaces, or adjacent platform ecosystems.
Background co-selling with technical teams such as Sales Engineering, Solutions Architecture, or Professional Services.
Familiarity with agentic commerce, payments concepts, including TPV, authorization rates, chargebacks, and cost of acceptance, or the curiosity to learn quickly.
Success scaling in fast-growing organizations where PLG and SLG coexist, including building or refining playbooks and metrics.
Proficiency with modern technical sales stacks, for example CRM, sales engagement, conversation intelligence, and value-selling tools.
Formal training in a sales methodology such as MEDDICC, Command of the Message, Challenger, or SPIN.

We are currently prioritizing candidates in the United States and Canada, Eastern Time preferred.

Salary range: $95,000-$160,000 USD, plus variable compensation. Please note that salary ranges are global, regardless of location, and we pay in local currency.

We are searching for high-caliber candidates with the skills and qualities to have a net positive for Automattic. Pay will reflect the potential contribution and the impact you can bring, which may, in some cases, go beyond the range stated.

This isn’t your typical work-from-home job—we are a fully-remote company with an open vacation policy. Read more about our compensation philosophy. To see a full list of benefits by country, consult our Benefits Page. And check out these links to learn more about How We Hire and What We Expect from Ourselves. #LI-DNI