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.

About you:

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.

Success in this role looks like:

• 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.

About Pressable

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 and Jetpack, Pressable provides the tools you need to reliably manage your WordPress websites with ease.

Salary range: $120,000 - $180,000 USD OTE. 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

• 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.

So, 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

WordPress VIP is the world’s leading enterprise content management platform. We help the world's largest companies (including Meta, Salesforce, and Disney) create innovative digital experiences with WordPress.

We’re looking for a Solutions Engineer to provide technical leadership to our Enterprise sales team, where you'll play a key part in building and maintaining the structure to support our sales programs. You’ll define and implement scalable processes and systems that deliver technical expertise, with a focus on consultative solution-based selling.

Responsibilities:

Partnering proactively with Sales and Customer Success to qualify new business opportunities in terms of technical requirements, competitive landscape, and business drivers.

• Identifying and solving customer problems proactively and creatively through effective project management and consultation on technical setup.
• Building proofs of concept and leading the demo process—including building, running, and training the team based on our buyer personas, verticals, and business priorities.
• Contributing to the RFP/RFI process as the primary point person on technical responses that Account Executives need assistance with.
• Recommending the integration strategies, enterprise architectures, platforms, and application infrastructure required to successfully implement a complete solution using best practices on our Cloud.

Requirements: 

• 5+ years experience in a Solutions Engineer or related position with customer-facing experience translating customer technical requirements into value discussions.
• Understanding of enterprise business models, content distribution, audience engagement and enterprise focused technical solutions.
• Experience with WordPress, PHP, or consulting experience.
• Demonstrated experience building Proofs of Concept and leading demo presentations.
• Worked closely with Account Executive teams developing solutions on complex sales opportunities.
• Outstanding communication; you should be great at holding people’s attention whether presenting, talking on the phone, or writing a quick blog post.

We are currently prioritizing candidates in the United States and Canada.

Salary range: $150,000-$200,000 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 for the right candidate.

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

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

At WordPress VIP (part of Automattic), we power the most influential properties on the web, from the White House to Meta and Salesforce. We are looking for a Forward Deployed Engineer (FDE) to join our mission in redefining how the world’s largest enterprises scale.

This isn't your typical engineering role; it’s an advanced, consultative position where you operate as a hands-on architect and a growth catalyst. As an FDE, you are the front line of trust, embedded with our most strategic customers to solve high-stakes technical challenges in real-time. By combining engineering excellence with deep customer proximity, you won’t just solve problems for customers, you’ll solve them with them, driving business expansion across the world’s most scaled environments. If you thrive in high-impact, ambiguous environments and want to help define the future of open-source technology at the enterprise level, we want to talk to you.

About the Team

The Customer Engineering and Architecture (CEA) team at WordPress VIP works directly with our most important customers to ensure they achieve their core technical outcomes and expand their investment in WordPress, VIP, and Automattic.

The team’s mission is to drive measurable technical success and long-term growth for VIP’s largest customers through a hands-on, scalable Forward Deployed Engineering practice that combines deep technical partnership with rapid, high-impact solutioning.

Role Overview

As a Forward Deployed Engineer (FDE), you will serve as an embedded technical partner to one or more complex WordPress VIP customers in Media, Enterprise, and Government.

You’ll work at the intersection of engineering, consulting, and customer success—diving deep into customer architectures, identifying and resolving complex technical challenges, and shaping scalable solutions that drive long-term adoption and expansion.

This is not a pure support or implementation role. It’s an advanced, consultative engineering position where you’ll operate as a hands-on architect, a trusted advisor, and a growth catalyst, helping customers succeed with WordPress VIP and related open-source technologies.

What You’ll Do

Deliver Customer Technical Outcomes

• Engage directly with large VIP customers (often embedded in their teams) to ensure successful adoption, integration, and scaling of WordPress VIP solutions.
• Directly identify and solve complex architectural and technical problems.
• Partner with customers as they leverage VIP’s support capabilities, ensuring they fully utilize VIP's high-availability support.
• Conduct technical discovery and design sessions, producing architecture recommendations, migration plans, and implementation guidance.
• Maximize the customer’s value from VIP’s platform, integrations, and partner ecosystem.

Drive Expansion Through Services-Led Growth

• Identify and shape professional services opportunities through ongoing technical engagement. Document and refer engagements to other VIP PS teams.
• Define scopes of work (SOWs) for technical expansion projects, collaborating closely with Services, Account Management, and Commercial teams.
• Participate in presales and renewal discussions as the technical voice of confidence and credibility.

Hold and Share Deep Customer Context

• Maintain a living technical knowledge base of customer architectures, deployments, and patterns.
• Act as the internal authority on assigned customer environments, proactively identifying risks and opportunities.
• Contribute to team-wide tooling and process improvements, including delivery platforms, AI workflows, and documentation systems (e.g., Rocketlane, Notion, or similar).

Contribute to the Forward Deployed Engineering Practice

• Using data, help refine the operating model for FDE engagements, balancing presence, value, and scalability.
• Experiment with and adopt AI-assisted workflows to improve delivery efficiency and insight generation.
• Collaborate with the leadership to expand the practice into a repeatable, revenue-driving function.

Qualifications

Required

• 5+ years of hands-on experience in web or application engineering, minimally in PHP and/or JavaScript.
• Strong familiarity with WordPress at scale, including common architectures, REST APIs, caching/CDNs, performance optimization, integration methods and security hardening.
• Experience working directly with large customers in technical consulting, architecture, or professional services.
• Proven ability to diagnose and resolve complex technical issues in distributed or high-traffic environments.
• Excellent communication and stakeholder management skills: equally comfortable in a debugging session and an executive briefing.
• Commercial mindset: ability to spot opportunities for value expansion and articulate ROI to non-technical stakeholders.

Ideal

• Experience with WordPress VIP, enterprise hosting, or similar SaaS/PaaS platforms.
• Prior experience as a solutions architect, senior developer, or forward deployed engineer in a consulting or SaaS/PaaS context.
• Familiarity with AI-assisted development, observability tools, and modern DevOps practices (CI/CD, GitHub Actions, etc.).
• Domain experience in Government, Media, or Enterprise.

Key Competencies

• Technical Depth & Breadth: Rapidly understand diverse architectures and technologies.
• Customer Empathy: Translate customer needs into actionable technical and business outcomes.
• Problem Ownership: Take responsibility for technical success, even beyond formal scope.
• Commercial Awareness: Balance engineering rigor with business objectives.
• Learning Agility: Continuously adapt to new tools, patterns, and customer contexts.
• Collaboration: Work fluidly with Services, Support, Product, and Commercial teams to deliver holistic outcomes.

Salary range: $180,000-$230,000 USD.  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