Automattic

Account Executive

• Own and manage larger, more complex agency and mid-market opportunities from discovery through close.
• Build and manage relationships with both technical contacts and executive or business decision-makers.
• Position Pressable’s platform as a long-term strategic partner for agencies and mid-market customers.
• Lead deep technical and business discovery to understand customer goals, constraints, and success criteria.
• Lead sophisticated opportunities involving multiple stakeholders, technical requirements, custom commercial structures, and non-standard deal terms.
• Act as the quarterback across the deal cycle, coordinating technical experts and internal partners to move opportunities forward efficiently.
• Deliver compelling presentations, solution walkthroughs, and business conversations tailored to the customer’s needs.
• Develop proposals, pricing recommendations, and commercial packages that align customer requirements with company goals.
• Lead contract and negotiation strategy in partnership with leadership, balancing creativity, customer value, and sound business judgment.
• Maintain comprehensive market awareness, including customer needs, competitive dynamics, and industry trends, and use those insights to strengthen deal strategy.
• Lead competitive positioning against alternative hosting platforms and infrastructure solutions, clearly articulating Pressable’s differentiation in performance, support, and partnership.
• Support successful onboarding and identify expansion opportunities by maintaining strong post-sale relationships with customers.
• Contribute to new business development through a mix of pipeline conversion, relationship-building, and proactive opportunity creation.
• Proactively build and execute strategic outbound plans into high-value target accounts, including named account mapping and executive-level outreach.
• Own an individual revenue quota across new logo acquisition and strategic expansion within larger agency and mid-market segments.
• Maintain disciplined pipeline management, forecasting, and deal documentation in HubSpot.
• Ensure opportunities are properly qualified, structured, and progressed with clear next steps.
• Identify expansion and long-term growth opportunities within high-value accounts.
• Use AI tools to support account research, discovery preparation, deal analysis, and follow-up drafting.
• Leverage call transcripts and AI-generated insights to identify objections, patterns, and next steps.
• Apply judgment to AI outputs, knowing when to rely on automation and when human decision-making is required.
• Collaborate with Solutions, Support, and Product teams to improve playbooks, pricing guidance, and feedback loops for strategic deals.
• Contribute structured product and market feedback based on real customer conversations.

Senior Sales Account Executive

• Own the full sales process from initial customer engagement through close for mid-market and agency new business opportunities.
• Build relationships with prospective customers and understand their business needs, technical requirements, and growth goals.
• Conduct discovery calls, solution discussions, and presentations that clearly communicate the value of Pressable’s managed WordPress hosting platform.
• Recommend the right products, packages, and terms to set customers up for long-term success.
• Prepare proposals, pricing, and quotes that align with customer requirements and standard company guidelines.
• Manage follow-up, pipeline progression, and next steps consistently across the sales cycle.
• Drive new business through a mix of company-generated opportunities, outbound prospecting, and relationship-based selling.
• Pull in technical or leadership partners when needed to support the deal and ensure customer confidence.
• Handle commercial conversations confidently and partner internally on non-standard contract or custom-term negotiations as appropriate.
• Support onboarding and maintain customer relationships that create opportunities for retention, upsell, and cross-sell.
• Stay informed on market trends, competitive offerings, and customer pain points to improve effectiveness and win rates.
• Own an individual revenue quota across new logo acquisition and strategic expansion within larger agency and mid-market segments.
• Maintain disciplined pipeline management, forecasting, and deal documentation in HubSpot.
• Ensure opportunities are properly qualified, structured, and progressed with clear next steps.
• Identify expansion and long-term growth opportunities within high-value accounts.
• Use AI tools to support account research, discovery preparation, deal analysis, and follow-up drafting.
• Leverage call transcripts and AI-generated insights to identify objections, patterns, and next steps.
• Apply judgment to AI outputs, knowing when to rely on automation and when human decision-making is required.
• Collaborate with Solutions, Support, and Product teams to improve playbooks, pricing guidance, and feedback loops for strategic deals.
• Contribute structured product and market feedback based on real customer conversations.

Sales Account Executive

Executive Assistant

• Partner with Matt and the Wranglers team as a trusted, behind-the-scenes operator.
• Triage priorities, block distractions, and manage logistics efficiently.
• Anticipate needs and handle urgent issues professionally.
• Interface with high-profile partners and board members with discretion.
• Conduct deep research and follow up for meeting preparations.
• Identify inefficiencies and suggest better workflows.

Executive Assistant – CEO

Product Manager

• Own product direction for payments product area
• Improve experiences across onboarding, checkout, refunds and disputes
• Raise quality by reducing failures and friction
• Use data to decide on next actions
• Collaborate with payments partners to improve integrations
• Keep stakeholders aligned through communication

Senior Product Manager, Payments

• Own and grow a $100M ARR strategic partnership, delivering a minimum of 30% year-over-year growth through disciplined pipeline development, commercial expansion, and joint go-to-market execution.
• Develop, maintain, and execute a rolling multi-year strategic partnership plan that aligns WooCommerce's roadmap and capabilities with the partner's commercial objectives and market position.
• Identify, scope, and close expansion opportunities—including new geographies, product lines, merchant segments, and revenue-share structures—that unlock mutual value.
• Define and track the commercial KPIs, milestones, and leading indicators that reflect the health and trajectory of the partnership.
• Build and sustain deep, trusted relationships across all levels of the partner organization, from C-suite and VP-level sponsors to operational and technical teams, ensuring alignment, advocacy, and momentum at every tier.
• Serve as the primary executive point of contact for the partner, driving QBRs, annual planning sessions, and escalation resolution with authority and credibility.
• Internally, act as the single accountable owner for the partnership, managing a broad set of stakeholders across product, engineering, marketing, legal, finance, and operations to secure alignment, investment, and execution commitment.
• Proactively manage partner satisfaction, anticipate friction points, and resolve issues before they become relationship risks.
• Lead the development and ongoing refinement of a comprehensive multi-year joint business plan, including growth targets, investment requirements, capability milestones, and market expansion priorities.
• Build and present compelling business cases to senior WooCommerce leadership to secure the resources, budget, and organizational commitment required to execute on the partnership strategy.
• Translate high-level strategic goals into phased, actionable execution plans, balancing ambition with operational realism, and managing progress rigorously.
• Drive accountability across internal teams through clear ownership assignment, milestone tracking, and regular executive reporting.
• Implement structured frameworks for ongoing partner evaluation using competitive analysis, industry benchmarks, and financial modeling—ensuring the partnership remains best-in-class relative to market alternatives.
• Maintain a deep, current understanding of the global payments ecosystem—including acquiring, PSPs, alternative payment methods, payment network rules, interchange economics, and bank transfer cost structures—and apply that knowledge to sharpen partnership strategy and commercial positioning.
• Actively monitor the market for emerging payment technologies, capabilities, and competitive dynamics that could enhance WooCommerce’s merchant value proposition, reduce underlying costs, or create new revenue opportunities through this partnership.
• Use technical fluency in payment capabilities to assess integration feasibility, validate business cases, and ensure that commercial terms are grounded in a clear understanding of product and operational realities.
• Translate payment capability gaps and merchant needs into concrete partnership priorities, working closely with product and engineering to align partner roadmap commitments with WooCommerce’s strategic direction.
• Drive global partnership growth by identifying and activating opportunities across geographies, adapting strategy to local market dynamics while maintaining a coherent global framework.
• Collaborate with marketing, product, and sales teams to develop and execute joint go-to-market initiatives, including co-selling, co-marketing, merchant acquisition programs, and partner-led revenue acceleration.
• Represent WooCommerce's strategic interests in commercial negotiations, contract renewals, and partnership expansions, crafting creative commercial structures that optimize for both strategic flexibility and economic outcomes.
• Establish and maintain robust reporting mechanisms to track partnership performance, commercial outcomes, and strategic milestones—delivering consistent, data-driven updates to senior leadership.
• Build scalable processes and frameworks that enable efficient collaboration between WooCommerce and the partner across geographies and functions.
• Manage contract amendments, commercial reviews, and renegotiations with rigor and commercial discipline.
• Thrive in ambiguity: able to define structure, process, and direction in fast-moving, resource-constrained environments where the path forward is unclear.

Global Account Director – Payment Partnerships

Revenue Operations

• Build core dashboards and analytics
• Establish data quality standards and governance
• Operationalize Customer Success function and create rules of engagement
• Support pricing and packaging changes with data
• Perform ongoing process and data gap analysis

Senior Revenue Operations Manager

Director

• Lead a 40+ person global Support and Engineering team operating 24/7
• Lead the continued build-out of an AI-augmented Support model
• Help set the strategic vision for Support and CX
• Coach and develop the bench of Support leads
• Shape VIP’s enterprise Support offering in partnership with Product, Sales, and CX
• Continue building best-in-class reporting on Support outcomes
• Engage credibly with senior internal and external stakeholders

Director of Support, WordPress VIP

• build an agentic Professional Services organization
• lead a Professional Services team of engineers and delivery managers
• own delivery quality end-to-end
• partner with Sales & Accounts to scope and price engagements accurately
• represent Professional Services credibly with senior internal and external stakeholders

Director of Professional Services, WordPress VIP

Support Engineer

• Manage, mentor, and develop a team of Technical Support Engineers, fostering a collaborative and high-performing environment that provides a world-class experience for our customers.
• Set clear performance goals and expectations, and ensure they are met by regularly assessing individual and team performance, as well as providing timely feedback and coaching.
• Lead by example as a player-coach, directly engaging with customers by answering complex technical questions, performing website performance audits, and migrating customer websites.
• Serve as a point of escalation, resolving complex or difficult customer interactions in a positive way.
• Identify, develop, and implement new strategies to drive improvements in customer satisfaction, team efficiency, and the overall quality of our product offering.
• Actively monitor and report on the performance of our support team to ensure standards, policies, and SLAs are consistently met or exceeded.
• Create and deliver training programs and materials to enhance the technical and customer-facing skills of the team.
• Manage scheduling, including reviewing and approving time-off requests, adjusting schedules for coverage, and arranging extra coverage from third-party contractors.
• Collaborate with the Head of Support to design and implement changes based on the needs of the department, the company, and our customers.
• Conduct scheduled one-on-one meetings with your team, taking time to connect with them as well as providing feedback and coaching to help them further develop in their career.

Technical Support Team Lead

• Partner with CEO and the Wranglers team as a trusted operator
• Triage priorities and block distractions for seamless operations
• Handle urgent issues and anticipate needs proactively
• Organize calendars, communications, travel, and project logistics
• Conduct research and follow-ups to fill gaps before they are noticed

Financial Planning and Analysis

• Lead deep dives on revenue and unit economics to identify growth opportunities, risks, and experiments that improve accuracy and business outcomes.
• Track the KPIs that matter, diagnose what’s driving them, and deliver clear recommendations to leaders.
• Own the monthly business reviews and QBR materials for the BUs you support, including the recommendations that turn each result into a decision.
• Write memos, build dashboards, and model scenarios that inform board and executive decisions.
• Build the financial analysis and forecasting models behind partnership, acquisition, and growth decisions.
• Partner with stakeholders in Marketing and Sales functions on performance analysis.

Senior Sales Account Executive

Sales Account Executive

Executive Assistant – CEO

Senior Product Manager, Payments

Global Account Director – Payment Partnerships

Senior Revenue Operations Manager

Director of Support, WordPress VIP

Director of Professional Services, WordPress VIP

Technical Support Team Lead

Executive Assistant – CEO

Strategic Finance Manager