Director, Expansion Sales

Director, Expansion Sales

United States, Remote

OfficeSpace Software provides the leading AI operating system for the built world, that helps teams plan, connect, and perform in the workplace. As a performance-based, PE-backed company, we hire based on merit and a willingness to do what it takes to succeed long-term. You're a great fit for the role if you're entrepreneurial, passionate, motivated by building at light speed, and an Agentic AI early adopter. Our world-class teams operate in the US, Canada, and Costa Rica in a culture of trust, respect, growth, and impact.

Role Summary

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.

You own net revenue retention — not just as a metric, but as a system. You design the segmentation strategy, resource allocation model, engagement architecture, and data infrastructure that turns customer value into durable, compounding revenue. At the same time, you are a hands-on leader who thrives in a fast-paced, customer-centric environment, motivating a team of Client Executives to exceed expectations and deliver meaningful results.

This is a strategic leadership role in a PE-backed SaaS environment. You will shape how we prioritize accounts, deploy talent, leverage AI, and create repeatable expansion plays that scale efficiently. If you are ready to make a significant impact at a company transforming the workplace, we want to hear from you.

What You'll Do

Own the Expansion Strategy

• 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.

Architect the Expansion Operating Model

• 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.

Leverage AI & Revenue Intelligence at Scale

• 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.

Lead Enterprise & Strategic Expansion

• 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.

Drive Cross-Functional Revenue Alignment

• 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.

Build a High-Performance Leadership Bench

• 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.

What You'll Bring

• Highly performative and disciplined operating rhythm along with the 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.

Why OfficeSpace?

• High-Performance Culture : At OfficeSpace, we believe in the power of accountability, focus, and drive. Our A-Player team members work together to deliver measurable, meaningful results. We recognize and reward 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. We seek individuals who are self-motivated and thrive in an environment where they can drive impactful outcomes.
• Technology-Forward : As a company invested in cutting-edge technology, we integrate AI and other advanced solutions across our platform to enhance productivity, customer experience, and process efficiency. Our team members are excited by the potential of AI and proactively explore ways it can drive our success.
• Growth Mindset : Continuous learning and improvement are integral to our culture. We encourage our team to embrace challenges, seek knowledge, and develop both personally and professionally.
• Innovation and Agility : We foster a dynamic, fast-paced environment where fresh ideas and bold solutions are celebrated. We embrace change and thrive on turning challenges into opportunities, with a team that is agile, proactive, and resilient.
• Collaborative, Results-Driven Environment : We value purposeful collaboration that leads to shared success and stronger results. While our team members are independent, they recognize the value of working together to drive our mission forward.
• Competitive Benefits and Rewards : OfficeSpace offers comprehensive and competitive benefits packages globally, designed to support our team's health, well-being, and financial security. We invest in our people so they can excel. OfficeSpace is committed to building and promoting a diverse workforce and celebrates the unique qualities that individuals of various backgrounds and experiences offer. We are committed to basing all employment-related decisions upon valid job-related factors without regard to race, color, sex (including pregnancy, sexual orientation, and gender identity), age, religion, national origin, genetic information, military status, veteran status, physical or mental disability, or any other status protected by law.