Senior Solutions Engineer at Automattic

About Automattic

Automattic is the company behind products like WordPress.com and WooCommerce, with a mission to democratize publishing and commerce on the web. It operates as a fully distributed global company with a strong commitment to open source and inclusivity.

Role Overview

Pressable is seeking a Senior Solutions Engineer to lead and scale its technical pre-sales function. This is a founding individual contributor role where you will partner closely with leadership to define the pre-sales engineering strategy, drive complex deals, and ensure successful customer onboarding.

You will serve as the technical authority throughout the sales cycle—guiding discovery, designing tailored solutions, and building confidence through demonstrations and performance validation. This role blends strategic thinking with hands-on technical execution, making it ideal for someone comfortable engaging both executives and engineering teams.

Key Responsibilities

• Own the end-to-end technical pre-sales process: discovery, solution design, demos, proposals, and migration planning.
• Partner with Sales, agency partners, and internal teams to win and accelerate strategic deals.
• Conduct technical discovery sessions to uncover architecture complexity, risks, and opportunities.
• Design and document migration strategies for WordPress environments (single-site, Multisite, WooCommerce), including database migration, DNS setup, caching/CDN, and performance optimization.
• Run pre-migration performance benchmarks and quantify improvements (TTFB, load time, reliability, cost savings).
• Build scalable pre-sales frameworks and assets (demo environments, benchmarking templates, qualification frameworks).
• Perform competitive analysis and position Pressable against alternatives such as WP Engine, Kinsta, and Pantheon.
• Act as a trusted technical advisor to developers, IT teams, and senior stakeholders.
• Provide structured handoff documentation to Customer Success/TAM teams post-sale.
• Represent Pressable in the WordPress ecosystem (events, webinars, content, community engagement).
• Leverage AI and automation to enhance pre-sales workflows, proposal quality, and operational efficiency.
• Share field insights with Product and Engineering to influence roadmap and positioning.

Requirements

• 5+ years’ experience in Solutions Engineering, Technical Pre-Sales, or Technical Consulting.
• Minimum 2+ years of hands-on experience with WordPress development.
• Strong understanding of modern web architecture, hosting infrastructure, and performance optimization.
• Proven ability to lead technical sales cycles and influence deal outcomes.
• Experience building technical proposals, architecture documentation, and migration runbooks.
• Familiarity with performance and diagnostic tools (e.g., Google PageSpeed Insights, GTmetrix, WP-CLI).
• Experience conducting TCO analysis, RFP responses, and competitive positioning.
• Strong communication skills with the ability to translate technical concepts into business value.
• Experience working cross-functionally with Sales, Product, and Engineering teams.
• Exposure to AI tools and automation workflows in technical environments is a strong advantage.

What Success Looks Like

• Increased technical win rates on strategic deals.
• Faster pipeline velocity through effective qualification and solutioning.
• High-quality customer onboarding and handoffs with minimal rework.
• Measurable performance improvements demonstrated in proposals.
• Creation of reusable pre-sales assets and frameworks.
• Strong credibility with internal teams, partners, and the broader WordPress community.
• Effective use of AI to automate repetitive tasks and improve efficiency.

About Pressable

Pressable is a leading managed WordPress hosting provider, delivering high-performance, scalable solutions for developers, agencies, and businesses. With deep integrations across the Automattic ecosystem, Pressable powers mission-critical websites with reliability and ease.

How to Apply

Interested candidates should

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