Back to jobs
New

Director, Expansion Sales

United States, Remote

About OfficeSpace: 

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. 

Create a Job Alert

Interested in building your career at OfficeSpace Software? Get future opportunities sent straight to your email.

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Select...

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in OfficeSpace Software’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.