[Hiring] Director, Expansion Sales @OfficeSpace Software

Role Description

We are building a world-class expansion engine designed to maximize customer lifetime value at scale. As Director, Expansion Sales, you are the architect and operator of our post-sale revenue strategy across a portfolio of 1,000+ accounts spanning SMB, Mid-Market, and Enterprise.

• Own net revenue retention—not just as a metric, but as a system.
• Design the segmentation strategy, resource allocation model, engagement architecture, and data infrastructure that turns customer value into durable, compounding revenue.
• Be a hands-on leader who thrives in a fast-paced, customer-centric environment.
• Motivate a team of Client Executives to exceed expectations and deliver meaningful results.
• Shape how we prioritize accounts, deploy talent, leverage AI, and create repeatable expansion plays that scale efficiently.

Qualifications

• Highly performative and disciplined operating rhythm along with a growth mindset and swagger.
• 8+ years of progressive B2B SaaS sales experience across renewals, expansion, and Enterprise selling.
• 3+ years leading quota-carrying teams with ownership of multi-segment portfolios.
• Proven experience managing large account bases (500–1,000+ accounts) with structured segmentation and coverage models.
• Demonstrated success building repeatable, scalable expansion systems—not just hitting a number.
• Deep understanding of NRR drivers, churn dynamics, expansion velocity, and lifetime value optimization.
• Experience leveraging AI-powered revenue tools (account scoring, predictive churn models, pipeline analytics, conversation intelligence).
• Proficiency in Salesforce and sales analytics platforms; comfort operating with board-level visibility.
• Executive presence with C-level and procurement stakeholders and the ability to drive change and cross-functional alignment.
• Bachelor's degree; MBA is a plus.

Requirements

• Define and evolve the multi-segment expansion strategy across 1,000+ accounts, balancing growth, retention risk, and resource allocation.
• Develop and deploy a strategic account planning model that drives durable revenue from our AI-native platform, rooted in client value.
• Design a long-term net revenue retention roadmap aligned to company valuation and growth objectives.
• Stay informed on market trends, competitor activity, and client feedback to continuously sharpen the approach.
• Build and refine a scalable operating system across upsell, cross-sell, strategic renewal, and whitespaces selling motions.
• Establish structured operating rhythms—forecasting cadences, territory design, account planning standards, and executive reviews—that drive clarity and accountability.
• Implement portfolio-level health scoring, whitespace modeling, and predictive renewal frameworks.
• Leverage Salesforce, conversational intelligence, AI, and other sales technologies to ensure accurate reporting, pipeline management, effective coaching, and operational visibility.
• Deploy AI-driven analytics to identify expansion signals, risk patterns, whitespace opportunities, and productivity gaps.
• Translate AI insights into standardized expansion playbooks embedded in daily workflows.
• Elevate forecasting through scenario modeling, risk-weighted projections, and leading-indicator dashboards.
• Serve as executive sponsor for high-value and complex accounts.
• Lead or support strategic negotiations and multi-year expansion agreements.
• Partner with Client Success to orchestrate proactive, value-led renewal strategies.
• Partner with Product, Marketing, and RevOps to refine packaging, pricing, and messaging that unlock expansion pathways.
• Provide structured feedback loops to inform product roadmap and competitive positioning.
• Influence compensation design, capacity planning, and territory modeling to optimize ROI.
• Provide senior leadership with regular insights on pipeline health, revenue forecasting, top-account strategies, and strategic opportunities.
• Recruit, mentor, and develop Client Executives capable of operating consultatively across segments.
• Foster a collaborative, goal-oriented culture that emphasizes accountability, continuous improvement, and innovation.
• Raise standards around deal strategy, account planning, and executive engagement.
• Instill forecasting rigor, pipeline hygiene, and data-driven decision-making across the team.

Benefits

• High-Performance Culture: We believe in accountability, focus, and drive, recognizing and rewarding those who push boundaries and achieve excellence.
• Ownership and Accountability: We trust our employees to take full ownership of their roles, providing the autonomy to innovate and the support to succeed.
• Technology-Forward: We integrate AI and other advanced solutions across our platform to enhance productivity, customer experience, and process efficiency.
• Growth Mindset: Continuous learning and improvement are integral to our culture, encouraging our team to embrace challenges and seek knowledge.
• Innovation and Agility: We foster a dynamic, fast-paced environment where fresh ideas and bold solutions are celebrated.
• Collaborative, Results-Driven Environment: We value purposeful collaboration that leads to shared success and stronger results.
• Competitive Benefits and Rewards: We offer comprehensive and competitive benefits packages globally, designed to support our team’s health, well-being, and financial security.