Director, Expansion Sales at OfficeSpace Software
United States, RemoteFull-timeRemoteSalesPosted about 1 month ago
Apply with PipelineAbout the Role
<div class="content-intro"><p><strong>About OfficeSpace: </strong></p>
<p>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. </p></div><p><strong><span data-contrast="none">Role Summary</span></strong><span data-ccp-props="{"201341983":0,"335559738":240,"335559739":240,"335559740":240}"> </span></p>
<p><span data-contrast="auto">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.</span><span data-ccp-props="{"201341983":0,"335559738":240,"335559739":240,"335559740":240}"> </span></p>
<p><span data-contrast="auto">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.</span><span data-ccp-props="{"201341983":0,"335559738":240,"335559739":240,"335559740":240}"> </span></p>
<p><span data-contrast="auto">This is a strategic leadership role in a PE-backed SaaS environment.</span><span data-contrast="auto"> </span><span data-contrast="auto">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.</span><strong><span data-contrast="none"> </span></strong><span data-ccp-props="{"201341983":0,"335559738":240,"335559739":240,"335559740":240}"> </span></p>
<p><strong><span data-contrast="none">What You'll Do:</span></strong><span data-ccp-props="{"201341983":0,"335559739":0,"335559740":240}"> </span></p>
<p><strong><span data-contrast="auto">Own the Expansion Strategy</span></strong><span data-ccp-props="{"201341983":0,"335559739":0,"335559740":240}"> </span></p>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="1" data-aria-level="1"><span data-contrast="auto">Define and evolve the multi-segment expansion strategy across 1,000+ accounts, balancing growth, retention risk, and resource allocation.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="2" data-aria-level="1"><span data-contrast="auto">Develop and deploy a strategic account planning model that drives durable revenue from our AI-native platform, rooted in client value.</span><span data-ccp-props="{"134233117":true,"134233118":true,"201341983":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="3" data-aria-level="1"><span data-contrast="auto">Design a long-term net revenue retention roadmap aligned to company valuation and growth objectives.</span><span data-ccp-props="{"134233117":true,"134233118":true,"201341983":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="4" data-aria-level="1"><span data-contrast="auto">Stay informed on market trends, competitor activity, and client feedback to continuously sharpen the approach.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<p><strong><span data-contrast="auto">Architect the Expansion Operating Model</span></strong><span data-ccp-props="{"201341983":0,"335559739":0,"335559740":240}"> </span></p>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="5" data-aria-level="1"><span data-contrast="auto">Build and refine a scalable operating system across upsell, cross-sell, strategic renewal and whitespaces selling motions.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="6" data-aria-level="1"><span data-contrast="auto">Establish structured operating rhythms—forecasting cadences, territory design, account planning standards, and executive reviews—that drive clarity and accountability.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="7" data-aria-level="1"><span data-contrast="auto">Implement portfolio-level health scoring, whitespace modeling, and predictive renewal frameworks.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="8" data-aria-level="1"><span data-contrast="auto">Leverage Salesforce, conversational intelligence, AI and other sales technologies to ensure accurate reporting, pipeline management, effective coaching and operational visibility.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<p><strong><span data-contrast="auto">Leverage AI & Revenue Intelligence at Scale</span></strong><span data-ccp-props="{"201341983":0,"335559739":0,"335559740":240}"> </span></p>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="9" data-aria-level="1"><span data-contrast="auto">Deploy AI-driven analytics to identify expansion signals, risk patterns, whitespace opportunities, and productivity gaps.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="10" data-aria-level="1"><span data-contrast="auto">Translate AI insights into standardized expansion playbooks embedded in daily workflows.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="11" data-aria-level="1"><span data-contrast="auto">Elevate forecasting through scenario modeling, risk-weighted projections, and leading-indicator dashboards.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<p><strong><span data-contrast="auto">Lead Enterprise & Strategic Expansion</span></strong><span data-ccp-props="{"201341983":0,"335559739":0,"335559740":240}"> </span></p>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="12" data-aria-level="1"><span data-contrast="auto">Serve as executive sponsor for high-value and complex accounts.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="13" data-aria-level="1"><span data-contrast="auto">Lead or support strategic negotiations and multi-year expansion agreements.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="14" data-aria-level="1"><span data-contrast="auto">Partner with Client Success to orchestrate proactive, value-led renewal strategies.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<p><strong><span data-contrast="auto">Drive Cross-Functional Revenue Alignment</span></strong><span data-ccp-props="{"201341983":0,"335559739":0,"335559740":240}"> </span></p>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="15" data-aria-level="1"><span data-contrast="auto">Partner with Product, Marketing, and RevOps to refine packaging, pricing, and messaging that unlock expansion pathways.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="16" data-aria-level="1"><span data-contrast="auto">Provide structured feedback loops to inform product roadmap and competitive positioning.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="17" data-aria-level="1"><span data-contrast="auto">Influence compensation design, capacity planning, and territory modeling to optimize ROI.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="18" data-aria-level="1"><span data-contrast="auto">Provide senior leadership with regular insights on pipeline health, revenue forecasting, top-account strategies, and strategic opportunities.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<p><strong><span data-contrast="auto">Build a High-Performance Leadership Bench</span></strong><span data-ccp-props="{"201341983":0,"335559739":0,"335559740":240}"> </span></p>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="19" data-aria-level="1"><span data-contrast="auto">Recruit, mentor, and develop Client Executives capable of operating consultatively across segments.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="20" data-aria-level="1"><span data-contrast="auto">Foster a collaborative, goal-oriented culture that emphasizes accountability, continuous improvement, and innovation.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="21" data-aria-level="1"><span data-contrast="auto">Raise standards around deal strategy, account planning, and executive engagement.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="11" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="22" data-aria-level="1"><span data-contrast="auto">Instill forecasting rigor, pipeline hygiene, and data-driven decision-making across the team.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<p><span data-ccp-props="{"134233279":false,"201341983":0,"335559685":720,"335559739":0,"335559740":240}"> </span></p>
<p><strong><span data-contrast="none">What You’ll Bring:</span></strong><span data-ccp-props="{"201341983":0,"335559739":0,"335559740":240}"> </span></p>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="1" data-aria-level="1"><span data-contrast="auto">Highly performative and disciplined operating rhythm along with the growth mindset and swagger.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="2" data-aria-level="1"><span data-contrast="auto">8+ years of progressive B2B SaaS sales experience across renewals, expansion, and Enterprise selling.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="3" data-aria-level="1"><span data-contrast="auto">3+ years leading quota-carrying teams with ownership of multi-segment portfolios.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="4" data-aria-level="1"><span data-contrast="auto">Proven experience managing large account bases (500–1,000+ accounts) with structured segmentation and coverage models.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="5" data-aria-level="1"><span data-contrast="auto">Demonstrated success building repeatable, scalable expansion systems—not just hitting a number.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="1" data-aria-level="1"><span data-contrast="auto">Deep understanding of NRR drivers, churn dynamics, expansion velocity, and lifetime value optimization.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="2" data-aria-level="1"><span data-contrast="auto">Experience leveraging AI-powered revenue tools (account scoring, predictive churn models, pipeline analytics, conversation intelligence).</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="2" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="1" data-aria-level="1"><span data-contrast="auto">Proficiency in Salesforce and sales analytics platforms; comfort operating with board-level visibility.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="1" data-aria-level="1"><span data-contrast="auto">Executive presence with C-level and procurement stakeholders and the ability to drive change and cross-functional alignment.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559739":0,"335559740":240}"> </span></li>
</ul>
<ul>
<li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridMultilevel"}" data-aria-posinset="2" data-aria-level="1"><span data-contrast="auto">Bachelor's degree, MBA is a plus.</span><span data-ccp-props="{"134233279":false,"201341983":0,"335559738":240,"335559739":0,"335559740":240}"> </span></li>
</ul><div class="content-conclusion"><p><strong data-stringify-type="bold">Why OfficeSpace?</strong></p>
<ul data-stringify-type="unordered-list" data-list-tree="true" data-indent="0" data-border="0">
<li data-stringify-indent="0" data-stringify-border="0"><strong data-stringify-type="bold">High-Performance Culture</strong>: 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.</li>
<li data-stringify-indent="0" data-stringify-border="0"><strong data-stringify-type="bold">Ownership and Accountability</strong>: 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.</li>
<li data-stringify-indent="0" data-stringify-border="0"><strong data-stringify-type="bold">Technology-Forward</strong>: 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.</li>
<li data-stringify-indent="0" data-stringify-border="0"><strong data-stringify-type="bold">Growth Mindset</strong>: Continuous learning and improvement are integral to our culture. We encourage our team to embrace challenges, seek knowledge, and develop both personally and professionally.</li>
<li data-stringify-indent="0" data-stringify-border="0"><strong data-stringify-type="bold">Innovation and Agility</strong>: 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.</li>
<li data-stringify-indent="0" data-stringify-border="0"><strong data-stringify-type="bold">Collaborative, Results-Driven Environment</strong>: 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.</li>
<li data-stringify-indent="0" data-stringify-border="0"><strong data-stringify-type="bold">Competitive Benefits and Rewards</strong>: 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.<br><br><em>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. </em></li>
</ul></div>
Related Roles
Account Executive, Mid-Market
OfficeSpace Software
United States, RemoteRemoteExecutive Chief of Staff
OfficeSpace Software
United States (Remote)RemoteSenior Site Reliability Engineer
OfficeSpace Software
United StatesGTM & Strategic Finance Associate
OfficeSpace Software
Mexico CitySenior UX Designer
OfficeSpace Software
United StatesLead Software Engineer
OfficeSpace Software
United States