Responsibilities
Strategic Deal Ownership
- 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.
Pipeline & Account Management
- 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.
AI-Assisted Sales Execution
- 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.
Cross-Functional Collaboration
- 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.
Requirements
- 6+ years of SaaS sales experience, including selling hosting-related solutions; managed hosting or WordPress hosting experience strongly preferred.
- Demonstrated success selling sophisticated, high-value solutions with longer or more consultative deal cycles.
- Experience selling to agencies, mid-market customers, or technical buyers.
- Strong discovery, consultative selling, and negotiation skills.
- Strong business acumen with the ability to connect customer needs to commercial outcomes.
- Excellent communication skills across both technical and non-technical audiences.
- Strong technical fluency, comfort, and credibility discussing WordPress, hosting, infrastructure, and platform-related concepts.
- Proven ability to negotiate creatively, manage complexity, and solve problems in a way that creates value for both the customer and the business.
- Strategic mindset with the ability to shape deal strategy, prioritize effectively, and operate with a high level of autonomy.
- Collaborative working style and a track record of partnering well across sales, marketing, product, support, and technical teams.
- Proficiency with CRM systems (e.g., HubSpot) and disciplined pipeline management.
- Comfort using AI-assisted sales tools to support research, preparation, follow-up, and deal analysis.