At WooCommerce, we're on a mission to democratize commerce through open source. As such, we’re now seeking an experienced Sales & Solutions Engineer to build our technical sales motion from the ground up — architecting merchant solutions that leverage the WordPress/WooCommerce ecosystem, strategic partner integrations, optimal hosting, and Automattic’s product portfolio.
You’ll work with technically-savvy midmarket merchants ($1M-$50M GMV) evaluating WooCommerce in competitive situations, architecting solutions that combine: WordPress/WooCommerce core + rich plugin ecosystem, Automattic products (WooPayments, Pressable/WPVIP/WP.com, Jetpack, Blaze), strategic partner integrations (payments, shipping, tax, marketing, POS, CRM/ERP), and agency partner services for custom development and implementation.
This is WooCommerce's Competitive Tip of the Spear.: The only team with the remit to directly and forcefully compete with our largest competitors in eCommerce. This team is the crucible for our messaging, value proposition, and technology at scale.
This is a builder role. If you thrive in 0→1 environments and urgency is in your blood, this is your role. You’ll set the playbook that defines how we sell for the next 18-24 months. Your on-the-ground feedback about what merchants need, what's blocking deals, and ecosystem gaps will directly shape our product roadmap, GTM strategy, time-to-first-value, and how we set up customers for retention and expansion.
What You’ll Do
Architect Solutions & Close (75%):
- Carry quota for net-new Midmarket merchants ($1M-$50M GMV), working primarily inbound, event, and partner-generated leads in competitive evaluations.
- Lead discovery and provide immediate value: Solve merchant problems from first conversation: answer technical questions, recommend plugins, troubleshoot architecture, suggest integrations. This consultative approach builds trust and accelerates closes.
- Architect comprehensive solutions blending WooCommerce core and plugins, WordPress plugins, strategic partner solutions (payments/shipping/tax/marketing/POS/ERP), hosting, Automattic products, and agency services.
- Navigate the open source ecosystem: Know which plugins/partners solve which problems, understand integration patterns, and advise when to build vs. buy vs. partner.
- Deliver demos that win: Customize to merchant use cases, adapt on the fly, make complexity simple. Build demo environments that showcase exactly what they need.
- Build compelling business cases: Show TCO across the platform, extensions, hosting, payments, and partners versus closed platforms.
- Position strategic partners (ShipStation, Avalara, Klaviyo, etc.) and coordinate bringing SMEs into deals.
- Own the close: Navigate procurement, address objections, deliver mutual action plans to signed contracts.
Build Culture, Playbooks & Enable (25%):
- Set the standard: Your solution patterns, integration blueprints, partner positioning, and qualification criteria become the playbook for scale.
- Be the voice of the market: Your frontline feedback influences product roadmap (which integrations to prioritize, where WooCommerce must evolve, missing pieces, etc.), customer lifecycle (onboarding patterns, retention risks, expansion signals for CS), and GTM strategy (pricing, packaging, positioning, competitive intelligence).
- Coordinate cross-BU: Work with Product on gaps/risks, Payment/Strategic Partnerships on co-selling, A4A Agency Partnerships on scalable enablement.
- Create repeatable assets: Solution templates, partner positioning guides, TCO calculators, competitive battle cards, discovery frameworks.
- Document what works: Deal patterns, merchant segmentation, when to engage partners, qualification frameworks.
- Enable internally: Train CS, Marketing, and Partnerships on solutions, ecosystem, and merchant needs.
What Success Looks Like:
- 90 days: First deals closed, key product gaps identified, feedback loops established.
- 6 months: Hitting quota, competitive playbook built, product roadmap influenced.
- 12 months: Team quota exceeded, playbooks adopted by new hires, foundation set for scale.
You Might Be a Fit If
Builder Mentality + Team-First:
- Bring urgency and competitive fire: we're under pressure and moving fast.
- Culture-setter: comfortable being “first", building playbooks, setting standards.
- Lift others up, lift all boats.
- Be pragmatic in ambiguity: we need to build without having perfect processes or systems.
- Speak truth to power with supporting data and bring proposed solutions.
- AI is a strength — with real examples from your current role.
- See teaching and knowledge transfer as core to the job.
Open Source Ecosystem Expertise:
- Deep WordPress/WooCommerce knowledge: extensions, plugins, themes, integration patterns, scalability, caching.
- Hands-on building experience: written custom functionality, integrated services, debugged conflicts, built prototypes.
- Partner landscape fluency: payment processors, shipping, tax, marketing automation, POS, inventory, ERP/CRM.
- Integration architecture: blend plugins, partner APIs, custom dev, and hosted services into coherent solutions.
- Open source philosophy: why merchants choose open platforms, economics of extensibility, flexibility vs. ease trade-offs.
Technical Foundation:
- 5-7+ years Solutions/Sales Engineering or technical sales with quota-carrying experience in Ecommerce/CMS/OSS/SaaS/platforms.
- Hands-on WordPress/WooCommerce development: you’ve built plugins, written hooks/filters, debugged integrations, and prototyped solutions.
- PHP fluency: read, write, debug—jump into code to solve problems or build quick POCs.
- Ecommerce platform expertise: merchant operations, checkout, payments, order management, inventory, fulfillment.
- Technical architecture: REST APIs, webhooks, SSO, caching/CDN, payments (auths, chargebacks, settlement), hosting, data/privacy.
- Integration debugging: trace issues across plugins, themes, APIs.
Commercial + Demo Excellence:
- Proven deal closer: you've owned a number and delivered.
- Solutions selling: ROI/TCO models, multi-threading, close through procurement/legal/security.
- Cross-product orchestration and complex buying processes.
- Creative demos: craft experiences that shift decisions, not just click through features.
- Competitive mastery: set landmines, surface requirements favoring open source, expose lock-in and hidden costs.
- Value selling: build cases showing why WooCommerce wins long-term—TCO, data ownership, flexibility.
- Strong storytelling: translate technical architecture into business narrative.
- Quick prototyping: spin up working examples to prove “can it do X?”.
- Showmanship without BS: build excitement but never overpromise.
- Communication across audiences: whiteboard with CTOs, present to CFOs, enable partners, train teams.
Preferred:
- Experience selling ecommerce platforms, open source CMS, payments/fintech, marketplaces.
- Understanding AI-driven commerce (autonomous agents, personalization APIs).
- Familiarity with compliance (PCI, SOC 2, SCA/PSD2, multi-region tax).
- PLG + SLG coexistence background, early-stage build-outs.
- Sales methodology training (MEDDPICC, Command of the Message, Challenger).
- OSS agency/SI partner ecosystem experience.
We are currently prioritizing candidates in the United States, Canada, the UK, and Ireland.
Salary range: $160,000-$185,000 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
About Automattic
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