Senior Solutions Engineer at Automattic

About Pressable

Founded in 2010, Pressable is a world-class managed WordPress hosting provider specializing in scalable, highly available services for agencies, builders, developers, and businesses. With industry-leading performance, 24/7 expert support, an award-winning control panel, advanced developer tools, and seamless integrations with WooCommerce and Jetpack, Pressable provides the tools you need to reliably manage your WordPress websites with ease.

Pressable is seeking a Senior Solutions Engineer to lead its pre-sales engineering efforts, focusing on acquiring and onboarding the right customers. As the foundational individual contributor in pre-sales, you will collaborate directly with the VP to define and standardize the technical sales process. You will partner with Account Executives and Agency Partners to qualify opportunities, design solutions, build confidence through demonstrations and migration planning, and ensure new customers successfully transition to our platform.

Your primary objective is proactive and deal-oriented, guiding prospects through technical discovery and solution definition while effectively highlighting Pressable's unique offerings and preparing them for a smooth handover to Customer Success teams. This role is ideal for someone comfortable discussing business outcomes with executives and, equally, debugging a slow query or benchmarking a migration environment on a server.

As a Solutions Engineer, You Will:

• Own the entire technical pre-sales process, from initial discovery and solution design to product demonstrations, technical proposals, and migration planning for prospective clients.
• Work closely with Sales, Woo, and Automattic for Agencies (A4A) on strategic opportunities, leveraging your technical expertise to become a trusted advisor for prospect developer teams, IT/operations, and leadership.
• Lead technical discovery conversations to uncover architecture complexities, risks, and opportunities, using these insights to construct compelling, appropriately scaled solutions for each prospect.
• Design migration plans for complex WordPress sites (single-site, Multisite, WooCommerce), covering database transfers, DNS strategy, caching/CDN configuration, performance optimization, and risk assessment, then seamlessly hand them off to the TAM or migration team for execution.
• Conduct pre-migration performance benchmarks and articulate how Pressable will demonstrably enhance a prospect's current environment in terms of TTFB, page load, stability, and operational savings.
• Develop and implement a scalable pre-sales engagement model, creating reusable assets (e.g., demo environments, standard performance benchmarks, technical qualification frameworks) to enable Account Executives to close standard deals independently.
• Perform competitive analysis, positioning Pressable against competitors like WP Engine, Kinsta, and Pantheon, with clear, factual TCO and performance comparisons.
• Represent Pressable within the broader WordPress community at WordCamps, agency partner events, webinars, and through published content, building Pressable's reputation as the technical choice for serious WordPress professionals.
• Provide structured, field-derived insights to Product and Engineering, influencing roadmap decisions and sales positioning.
• Ensure a clear, documented handover to the TAM upon deal closure, including full context on the customer's architecture, risk areas, goals, open items, and initial 90-day priorities.
• Explore the frontiers of AI in hosting by experimenting with new AI-driven application layer interactions, redesigning customer platform engagement, and integrating adjacent systems. Translate these field learnings into commercially viable, AI-powered product ideas (e.g., auto-generated performance analyses, migration runbooks, or risk maps) that expand the platform's capabilities for prospects and accounts.
• Guide discussions with senior prospect leadership on technical and product strategy, trade-offs, and risk management during the evaluation process.

About You:

You are driven by success, by building technical conviction in prospects, overcoming objections, and witnessing complex deals close due to your efforts. You operate proactively, bring structure to ambiguous situations, and create lasting assets beyond individual deals. You are an expert at using AI tools to streamline pre-sales workflows while maintaining human oversight. You view the handover to the TAM as a critical deliverable, understanding its importance for the entire customer journey.

In addition, you have experience with:

• Leading the technical pre-sales motion for a SaaS, managed hosting, or platform product, learning from both wins and losses in technical evaluations.
• Collaborating closely with Sales teams as a technical sales partner, focusing on pre-sales solutions engineering, implementation planning, and driving new revenue.
• Developing technical proposals, architecture documents, and migration runbooks for complex WordPress environments.
• Translating performance and reliability improvements into tangible commercial value for customers, such as increased conversion, revenue, reduced support load, and operational savings.
• Competitive positioning, including TCO analyses, RFP responses, and head-to-head comparisons, leveraging your platform's strengths.
• Influencing prospect decisions using tools like GTMetrix, Lighthouse, Google PageSpeed Insights, WP-CLI, and wp-doctor.
• Evaluating and selecting AI and automation tools that enhance observability, troubleshooting, and proposal quality without adding complexity.
• Community presence, demonstrated by speaking at WordCamps, publishing technical content, or contributing to the WordPress ecosystem.
• Maintaining composure and decisiveness in high-stakes, fast-moving sales scenarios.
• Distilling customer goals and complex technical requirements into concrete next steps and clear proposals.
• Proven experience in solutions engineering or technical pre-sales within the web hosting or CMS ecosystem, with a deep understanding of modern web architectures and server-side performance, and the ability to rapidly master Pressable's WP Cloud infrastructure.
• 2+ years of WordPress development experience (required).
• 5+ years of overall experience in solutions engineering, pre-sales, or technical consulting (preferred).
• Outstanding verbal and written communication skills for effective interaction with both technical and non-technical stakeholders.
• In-depth knowledge of WordPress and managed hosting, specifically articulating the advantages of WP Cloud over traditional containerized or shared managed hosting.
• Strong analytical and problem-solving skills to quickly diagnose and scope technical risk during the pre-sales cycle.
• High attention to detail in technical specifications, proposals, and migration plans.
• Ability to collaborate with Sales, Support, Product, and Engineering to build a cohesive, winning technical narrative.
• Driving customer-specific innovation by adopting a senior architect's mindset, encouraging customers to embrace new deployment models, AI-assisted developer workflows, and system interactions for an AI-first architecture with reduced manual oversight.

Success in this Role Looks Like:

• Higher technical win rate on strategic deals you are involved in (your primary metric).
• Establish clear Rules of Engagement (ROE) with the Sales team, defining when and how the Solutions Engineer engages to maximize pipeline velocity and technical win rates.
• Increased pipeline velocity on complex opportunities through swift, confident technical qualification.
• High-quality pre-sale handoffs to the TAM requiring minimal rework post-close.
• Documented measurable performance gains in proposals between the prospect's current environment and Pressable.
• Strong positive feedback from Sales, A4A Partner Managers, and Agency Partners on the clarity of your plans and the credibility you add to their process.
• Reusable pre-sales assets that empower Sales and A4A to handle standard deals without Solutions Engineer involvement.
• Documented improvements in proposal quality, deal cycle time, or migration planning accuracy, driven by effective use of AI and automation in your workflow.
• Pressable's technical brand growth in the WordPress community through your visibility and contributions.
• Repetitive pre-sales tasks, such as benchmark reporting, runbook generation, proposal drafting, and log triage, are automated or AI-assisted wherever possible, freeing your time for high-judgment tasks only you can perform.

Perks & Benefits of Joining Pressable:

• Health Benefits for US-based staff (99% Paid Employee Medical, Dental, and Vision).
• Matching 401(k) for US-based staff.
• Life and Disability Insurance for US-based staff (100% Paid Life, & LTD).
• Work from home with home office setup and coworking allowances.
• Open vacation policy (no set number of days per year).
• Hardware and software, books or conferences that promote continued learning.

Are you ready to embark on this thrilling WordPress adventure? We can't wait to welcome you to the Pressable team and empower you to make the web a better place. Come join us in crafting an exceptional customer experience and revolutionizing the world of WordPress hosting. Apply now and let's build something amazing together! #LI-Remote

About Automattic

Now in our 20th year, we are the people behind WordPress.com, WooCommerce, Beeper, Tumblr, Simplenote, Jetpack, Longreads, Day One, PocketCasts, and more. We believe in making the web a better place. We are a distributed company with more than 1500 Automatticians in nearly every corner of the globe, speaking over a hundred different languages. Enriched by this diversity, we are united by a singular mission: to democratize publishing, commerce, and messaging so anyone with a story can tell it, anyone with a product can sell it, and everyone can manage their communications from a single source. In short, we help maintain a balance in society, creating and continually refining powerful tools people can use to compete fairly, regardless of income, gender, politics, language, or where they live in the world. We believe in Open Source, and the vast majority of our work is available under the GPL. Automattic is a Most Loved Company, an Equal Opportunity employer, and Disability Confident Committed. If you need disability-related accommodations during the application or interview process, please fill out this form. We are committed to ensuring an accessible hiring process for all candidates. Learn more about our Employee Resource Groups. You can track your application status and more at MyGreenhouse. To learn about how we handle your data, please review our Privacy Policy. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran.