Strategic Mid‑Market WordPress Sales Executive (Remote)

Webhosting; United States; On-site; USD 140,000 - 200,000; Full time

Benefits offered by this job

Health Benefits for US-based staff (99

Matching 401(k) for US-based staff.

Life and Disability Insurance for US‑$

Job summary

Pressable, a world-class WordPress hosting provider, seeks an experienced Sales Account Executive to drive growth with agencies and mid-market customers. You will own opportunities end-to-end, from discovery to close, while serving as a trusted advisor for high-scale needs.

You’ll report to the Head of Sales & Enablement and collaborate with Solutions, Support, and Product teams, leveraging AI to enhance research, prep, and insights while preserving human judgment in decisions.

Responsibilities

• 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.

Job description

Pressable, a world-class WordPress hosting provider, seeks an experienced Sales Account Executive to drive growth with agencies and mid-market customers. You will own opportunities end-to-end, from discovery to close, while serving as a trusted advisor for high-scale needs.

You’ll report to the Head of Sales & Enablement and collaborate with Solutions, Support, and Product teams, leveraging AI to enhance research, prep, and insights while preserving human judgment in decisions.