Senior Solutions Engineer, Pressable at Automattic

**Who this is for** This role is for a seasoned technical professional who excels at bridging the gap between business outcomes and technical architecture, serv

Work type: remote

Location: Remote

Salary: $120,000 – $175,000/yr

Type: Full-time

Summary

**Who this is for** This role is for a seasoned technical professional who excels at bridging the gap between business outcomes and technical architecture, serving as the foundational pre-sales expert for Pressable’s platform. **Key highlights** You will lead the entire technical sales lifecycle, from initial discovery and complex migration planning to performance benchmarking and competitive positioning, while helping shape the future of the company's pre-sales engagement model. **You might be a good fit if you...** - Possess deep hands-on expertise in WordPress, WooCommerce, and server-level troubleshooting. - Have a proven track record of architecting migration strategies for complex enterprise-level sites. - Are comfortable acting as a trusted advisor to both technical engineering teams and C-suite executives. - Can create scalable sales assets and frameworks that enable internal teams to close deals more effectively.

Job Description

Pressable is hiring a Senior Solutions Engineer to own our pre-sales engineering motion and help us win and onboard the right customers.

As our founding pre-sales individual contributor, you’ll partner directly with the VP to define and codify our technical sales motion.

You will partner with Account Executives and Agency Partners to qualify opportunities, architect the right solutions, build confidence through demonstrations and migration planning, and ensure new customers land on our platform with a clear path to success.

Your primary motion is proactive and deal-oriented: guiding prospects through technical discovery and solution definition while effectively differentiating Pressable’s products and services and setting prospects up for successful handoff to Customer Success teams.

This role is ideal for someone equally comfortable talking to executives about business outcomes and logging into a server to audit a slow query or benchmark a migration environment.

As a Solutions Engineer, you will:

• Own the technical pre-sales process end-to-end, from discovery and solution design through product demonstrations, technical proposals, and migration planning for prospective customers.

• Partner closely with Sales, Woo, and Automattic for Agencies (A4A) on strategic opportunities, leveraging your technical expertise to become the trusted advisor to prospect developer teams, IT and operations teams, and leadership.

• Lead technical discovery conversations that surface architecture complexity, risk, and opportunity, and use those findings to build a compelling, right-sized solution for each prospect.

• Architect migration plans for complex sites (single-site, Multisite, WooCommerce), including database moves, DNS strategy, caching/CDN configuration, performance tuning, and risk mapping, and then hand off cleanly to the TAM or migration team for execution.

• Run pre-migration performance benchmarks and document the case for how Pressable will measurably improve a prospect’s current environment (TTFB, page load, stability, ops savings).

• Design and implement a scalable pre-sales engagement model, creating reusable assets (demo environments, standard performance benchmarks, technical qualification frameworks) that empower Account Executives to confidently close standard deals without SE intervention.

• Conduct competitive analysis and position Pressable against other hosts (WP Engine, Kinsta, Pantheon, etc.) with clear, factual TCO and performance comparisons.

• Represent Pressable in 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.

• Feed structured, field-sourced insights back to Product and Engineering from what you’re seeing in pre-sales conversations, contributing to roadmap decisions and sales positioning.

• Provide a clean, documented handoff to the TAM at deal close, including full context on the customer's architecture, risk areas, goals, open items, and first-90-days priorities.

• Push the boundaries of AI in hosting by going beyond day-to-day usage: experiment with new AI-driven ways to work with the application layer, redesign how customers interact (or don’t need to interact) with the platform, and integrate adjacent systems; then turn field learnings into commercially grounded, AI-powered product ideas (for example, auto-generated performance analyses, migration runbooks, or risk maps) that expand what the platform can do for prospects and accounts.

• Steer discussions with senior prospect leadership regarding technical and product strategy, trade-offs, and risk management during the evaluation process.

You are motivated by winning; by building technical conviction in a prospect, removing the last objection, and watching a complex deal close because of the work you did. You operate proactively, create structure in ambiguous situations, and build assets that outlive any single deal.

You’re an expert at experimenting with AI tools to remove friction and accelerate your pre-sales workflow, while keeping human judgment in the loop. You view the handoff to the TAM as a core deliverable, not an afterthought—because a clean handoff is what makes the rest of the customer journey work.

In addition, you have experience with:

• Leading the technical pre-sales motion for a SaaS, managed hosting, or platform product. You’ve been the person who wins or loses the technical evaluation, and you've learned from both.

• Collaborating closely with Sales teams as their technical sales partner, on primarily pre-sales solutions engineering, implementation planning, and driving new revenue opportunities.

• Building technical proposals, architecture documents, and migration runbooks for complex WordPress environments.

• Translating performance and reliability improvements into clear commercial value for customers: conversion, revenue, support load reduction, operational savings.

• Competitive positioning: you’ve done TCO analyses, RFP responses, and head-to-head comparisons, and you know how to play to 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 improve observability, troubleshooting, and proposal quality without adding unnecessary complexity.

• Community presence: you've spoken at WordCamps, published technical content, or contributed to the WordPress ecosystem in ways that build credibility with agency and developer audiences.

• Remaining composed and decisive in high-stakes, fast-moving sales situations.

• 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. You must possess a deep understanding of modern web architectures and server-side performance, paired with the aptitude to rapidly master Pressable’s specific 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 to effectively interact with both technical and non-technical stakeholders.

• In-depth knowledge of WordPress and managed hosting, with the specific ability to articulate the distinct advantages of WP Cloud over traditional containerized or shared managed hosting.

• Strong analytical and problem-solving skills to diagnose and scope technical risk quickly during the pre-sales cycle.

• High attention to detail in technical specifications, proposals, and migration plans.

• Ability to work collaboratively with Sales, Support, Product, and Engineering to build a cohesive, winning technical narrative.

• Drive customer-specific innovation by thinking like a senior architect: challenging customers to adopt new deployment models, explore AI-assisted developer workflows, and reimagine how their systems interact so they can achieve an AI-first architecture with less manual oversight and human intervention.

• Higher technical win rate on strategic deals where you are involved. This is your primary metric.

• Establish clear Rules of Engagement (ROE) with the Sales team, defining exactly when and how the Solutions Engineer is attached to an opportunity to maximize pipeline velocity and technical win rates.

• Pipeline velocity increases on complex opportunities through fast, confident technical qualification.

• High-quality pre-sale handoffs to the TAM that require minimal rework post-close.

• Measurable performance gains documented in proposals between the prospect’s current environment and Pressable.

• Strong 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 improve Sales’ and A4A’s ability 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 grows in the WordPress community through your visibility and contributions.

• Repetitive pre-sales tasks—benchmark reporting, runbook generation, proposal drafting, log triage—are automated or AI-assisted wherever possible, freeing your time for the high-judgment work that only you can do.

Founded in 2010, Pressable is a world-class managed WordPress hosting provider that specializes 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](https://woocommerce.com/) and[ Jetpack](https://jetpack.com/), Pressable provides the tools you need to reliably manage your WordPress websites with ease.

Salary range:$120,000 - $175,000 USD plus variable compensation. Please note that while salary ranges are presented here in USD, we will pay in local currency.

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

[Perks & Benefits of Joining Pressable](https://pressable.com/careers/)

• 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.

About Automattic

Now in [our 20th year](https://timeline.automattic.com/), we’re the people behind [WordPress.com](http://wordpress.com/), [WooCommerce](https://href.li/?http://woocommerce.com/), [Beeper](https://www.beeper.com/), [Tumblr](https://href.li/?https://www.tumblr.com/), [Simplenote](https://href.li/?http://simplenote.com/), [Jetpack](https://href.li/?http://jetpack.com/), [Longreads](https://href.li/?http://longreads.com/), [Day One](https://href.li/?https://dayoneapp.com/), [PocketCasts](https://href.li/?https://www.pocketcasts.com/), and more. We believe in making the web a better place.

We’re 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’re 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](https://github.com/Automattic), and the vast majority of our work is available under the [GPL](https://en.wikipedia.org/wiki/GNU_General_Public_License). Automattic is a [Most Loved Company](https://mostlovedworkplace.com/companies/automattic-inc/), an Equal Opportunity employer, and [Disability Confident Committed](https://disabilityconfident.campaign.gov.uk/). ([Here’s what that might mean for you](https://happinessengineer.blog/2022/09/08/happiness-for-everyone-working-with-a-disability-at-automattic/).) If you need disability-related accommodations during the application or interview process, please [fill out this form](https://automattic.com/disability-related-accommodation-request/). We are committed to ensuring an accessible hiring process for all candidates. Learn more about our [Employee Resource Groups](https://automattic.com/automattician-resource-groups/).

You can track your application status and more at [MyGreenhouse](https://my.greenhouse.io/users/sign_in).

To learn about how we handle your data, please review our [Privacy Policy](https://automattic.com/privacy/).

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