Role Summary: 

You’ll lead how AI actually works at OfficeSpace—not as a side project, but as a core system. As a Full-Stack Software Engineer, you will contribute to the evolution of our AI platform from production-ready chat experiences to agentic workflows that operate safely at enterprise scale. You’ll build, harden, and scale systems that connect AI services, a Rails backend, and a React frontend—while setting the technical bar for performance, reliability, and integrity. 

We move fast. We expect precision. And we trust you to own outcomes. 

What You’ll Do: 

• Build out OfficeSpace’s AI platform—starting with our customer-facing chatbot and extending into agentic workflows and MCP server capabilities. 

• Design and operate Python-based AI services that integrate deeply with our Ruby on Rails backend and React frontend. 

• Partner with AI agents to accelerate development, testing, debugging, and code reviews.  

• Orchestrate AI-assisted workflows to generate, validate, and optimize production-ready code.  

• Deliver clean, well-tested features across multiple projects—on time and at high quality.  

• Optimize applications across browsers, devices, and environments—making smart trade-offs.  

• Work across data layers, from relational databases (MariaDB) to search and caching systems (Redis, Elasticsearch), to Vector DBs. 

• Contribute to evolving best practices in AI-augmented software development. 

What You Bring: 

• 3–5 years of backend development experience with Ruby on Rails or Python.  

• Experience building AI features is a plus 

• Strong proficiency in JavaScript (ES6+) and modern React development.  

• Experience building and scaling production-grade web applications.  

• Solid understanding of databases—relational and exposure to NoSQL systems.  

• Ability to work across multiple projects and deliver with consistency.  

• Experience or exposure to GraphQL is a plus.  

• AI fluency—comfortable using AI tools for coding, debugging, testing, and documentation.  

• Strong problem-solving skills and the judgment to balance speed vs. quality.  

• A builder mindset—you take ownership, move fast, and continuously improve how work gets done. 

Role Summary: 

You own the performance, reliability, and cost efficiency of OfficeSpace’s production platform at scale. As a Senior Site Reliability Engineer, you shape how our systems run—fast, resilient, and predictable—while leading the shift from manual operations to AI-assisted reliability engineering. We provide the platform. You make it perform. 

What You’ll Do: 

• Drive measurable improvements in latency, throughput, and availability across a large-scale production environment. 

• Own system performance—from Linux internals to Kubernetes scheduling—and eliminate bottlenecks before customers feel them. 

• Define and enforce SLIs, SLOs, and error budgets that balance speed, reliability, and growth. 

• Partner with application engineers to profile code paths, improve execution efficiency, and harden services under real load. 

• Lead database performance optimization across queries, indexing, replication, and workload isolation. 

• Design and oversee AI-assisted load testing, stress testing, and capacity planning workflows. 

• Guide the migration from monolithic deployments to multi-tenant Kubernetes platforms. 

• Reduce infrastructure spend through architectural decisions, right-sizing, and intelligent scaling strategies. 

• Build and supervise automation for infrastructure provisioning, configuration management, and observability. 

• Set clear operational standards for reliability, performance, and incident response—and raise the bar for how we run production. 

 What You Bring: 

• 7+ years operating and evolving large-scale production systems. 
  Deep Linux systems expertise with hands-on performance tuning across CPU, memory, disk, and networking. 

• Strong Python skills for automation, tooling, and AI-assisted systems workflows. 

• Production experience with Ruby/Rails ecosystems, including Puma and Sidekiq. 

• Proven ability to diagnose and resolve complex database performance issues (MySQL/MariaDB or PostgreSQL). 

• Advanced Kubernetes experience—workload sizing, scheduling, and multi-tenant operations. 

• Infrastructure-as-code mastery using Terraform and Terragrunt. 

• Experience with configuration management tools such as Puppet or Ansible. 

• Strong observability instincts across metrics, logs, and traces using tools like Prometheus, Grafana, Datadog, or ELK. 

• AI fluency—comfortable supervising AI agents for analysis, testing, and reporting, and validating their outputs. 

• A builder mindset. You move fast, take ownership, and raise standards. 

 Preferred Background: 

• Scaling and refactoring monolithic applications under real production load 

• Extracting databases or stateful components from monoliths 

• Apache and Nginx tuning at scale 

• Redis performance optimization and operational management 

• CI/CD systems and GitOps workflows, including ArgoCD 

• Cloud cost optimization and FinOps-aligned operational practices 

Role Summary: 

You will shape how we understand, forecast, and accelerate revenue. You’ll connect data across Marketing, Sales, Customer Success, and Finance—and turn that clarity into actions that move the business forward. You learn fast, you ask sharp questions, and you turn complexity into signal. We’ll trust you with high-impact work from day one. 

What You’ll Do: 

• Build a clear, end-to-end view of how we generate and retain revenue—from acquisition to expansion. 
• Analyze funnel, pipeline, revenue, and retention performance to surface the drivers that matter most. 
• Create financial and operational models that guide planning and inform strategic choices. 
• Own ongoing forecasts and reporting, giving leaders a crisp read on performance vs. expectations. 
• Deliver variance analyses with direct recommendations that increase clarity and decision velocity. 
• Shape pricing, packaging, and GTM investment decisions through quantitative insight. 
• Partner across teams to accelerate execution and strengthen accountability. 
•  Use AI tools to speed analysis, streamline reporting, and automate repetitive workflows. 
• Identify new opportunities to apply AI for forecasting, data processing, and operational efficiency. 

What You Bring:

• 3–5+ years in finance, consulting, RevOps, analytics, or another cross-functional role (SaaS preferred). 
• Strong analytical skills and modeling fundamentals; you enjoy turning data into direction. 
• Understanding of financial statements, SaaS economics, and revenue mechanics. 
• Experience with CRM, BI tools, or SQL is a plus. 
• Exceptional communication—you translate complexity into clarity.
• Curious, resourceful, and energized by fast-moving environments. 
• Comfortable working with (and supervising) AI-enabled workflows
• Ability to audit AI output, stress-test assumptions, and turn recommendations into action. 

Role Summary: 

You win new logos. Full stop. As a Mid-Market Account Executive, you own the end-to-end motion of bringing new customers into OfficeSpace. You run disciplined, value-led sales cycles with senior decision-makers and use AI-powered tools to prospect smarter, sell faster, and close with confidence. We give you a market-leading platform. You turn it into revenue. 

What You’ll Do: 

• Own new-logo acquisition across a defined Mid-Market territory—build pipeline, run deals, and close. 

• Lead buyer-driven, value-based sales cycles with C-level, VP, and Director stakeholders. 

• Orchestrate AI-assisted prospecting to identify high-intent accounts and create net-new opportunities. 

• Translate workplace, facilities, and real estate challenges into clear, quantifiable business value. 

• Deliver sharp, compelling product demos that connect OfficeSpace capabilities to real-world outcomes. 

• Guide AI-generated proposals, pricing models, and forecasts—ensuring accuracy, clarity, and impact. 

• Negotiate contracts and commercial terms with confidence and discipline. 

• Maintain rigorous pipeline hygiene and forecasting using Salesforce and revenue intelligence tools. 

• Partner with Marketing and Business Development to accelerate deal velocity and improve win rates. 

• Share frontline market feedback to shape product strategy and go-to-market execution. 

• Consistently meet—and outperform—new logo revenue targets. 

What You'll Bring: 

• Bachelor’s degree in Business, Marketing, or a related field. 

• Proven Mid-Market B2B SaaS sales experience closing new business with senior buyers. 

• Track record of hitting and exceeding quota in outbound-driven roles. 

• Deep comfort running full-cycle sales without reliance on a BDR. 

• Strong discovery, storytelling, presentation, and negotiation skills. 

• Experience selling into Facilities, Workplace, HR, IT, Finance, or Real Estate functions. 

• Fluency with modern sales tools (Salesforce, SalesLoft, Gong, LinkedIn Sales Navigator or similar). 

• Ability to audit and improve AI-generated outreach, deal insights, and forecasts. 

• High ownership mindset—you run your book like a business. 

• Grit, curiosity, and a relentless drive to win. 

• Willingness to travel when needed. 

Role Summary: 

You own growth at the highest level. As a Client Executive – Enterprise, you build, expand, and protect strategic relationships across complex organizations with our highest value clients. You operate as a value architect, and executive partner to drive strategic and transformational client value - using data, AI, and sharp commercial discipline to grow enterprise accounts. 

What You Will Do 

• Own and grow a portfolio of high-value strategic accounts by developing and executing multi-year expansion strategies aligned to each client’s business priorities. 

• Develop and execute strategic account plans that translate client priorities into actionable expansion plays with clear value hypotheses, timelines, and deal strategies. 

• Create and close pipeline proactively - not tied to renewal cycles - by identifying whitespace, shaping opportunities, and aligning to executive-level priorities within your accounts. 

• Lead complex, multi-threaded sales motions by engaging economic buyers and key stakeholders across business, finance, and operations to build consensus and urgency. 

• Sell platform-level solutions, not product features, positioning OfficeSpace as a mission-critical operating system that drives measurable business outcomes. 

• Partner closely with Client Success, Product, and Solutions teams to orchestrate account strategy, unlock new use cases, and ensure successful adoption that fuels expansion. 

• Drive executive conversations that connect OfficeSpace capabilities to enterprise-level initiatives such as cost optimization, workforce productivity, and real estate strategy. 

• Operate with rigor and discipline in pipeline and deal management, maintaining high-quality opportunities, accurate forecasting, and clear progression toward close. 

• Continuously expand deal scope and value, moving beyond initial use cases to broader platform adoption across workplaces, assets, and employee experience. 

• Act as the quarterback of your accounts, ensuring alignment across all internal and client stakeholders to deliver both client impact and commercial outcomes. 

What You’ll Bring: 

• Bachelor’s degree. 

• 5–10+ years of SaaS sales experience across Mid-Market and Enterprise segments  

• Proven experience in complex B2B or enterprise sales, with a track record of creating and closing large, multi-stakeholder deals (not just managing renewals or transactional upsells). 

• Demonstrated ability to build pipeline within existing accounts, identifying and developing opportunities independent of contract timing. 

• Strong executive presence, with the ability to engage and influence C-level stakeholders (CFO, COO, CIO) through business-focused conversations. 

• Strategic thinking and deal-shaping capability, including the ability to translate ambiguous client needs into clear expansion strategies and compelling value propositions. 

• Experience selling platform or multi-product solutions, with a focus on outcomes, ROI, and long-term transformation rather than features. 

• Exceptional discovery and multi-threading skills, consistently building relationships across functions and levels within an organization. 

• High level of ownership and accountability, operating with a “CEO of the account” mindset and a bias toward action and results. 

• Ability to collaborate cross-functionally, leveraging Client Success, Product, and technical teams to drive both adoption and expansion. 

• Comfort operating in a high-change, performance-driven environment, with clear expectations around pipeline creation, deal quality, and quota attainment. 

• Intellectual curiosity and business acumen, enabling you to understand client industries, uncover strategic opportunities, and connect them to OfficeSpace’s platform value. 

Role Summary: 

You own the engine that drives retention, expansion, and long-term customer value. As Director of Client Success & Renewals, you lead a high-impact function across mid-market and enterprise accounts—building a system that turns customers into advocates and renewals into predictable revenue. You’ll lead a Manager and their team while shaping strategy, process, and AI-enabled execution across the full customer lifecycle. 

What You’ll Do: 

• Build and lead a high-performing Client Success & Renewals function across mid-market segments  

• Own net revenue retention (NRR), gross retention, and renewal forecasting accuracy  

• Lead, coach, and scale a manager and their team of CSMs and Renewal Specialists  

• Design the renewal motion—proactive, data-driven, and expansion-oriented  

• Implement AI-driven workflows for health scoring, churn prediction, and renewal risk detection  

• Drive executive-level customer engagement for high-value and at-risk accounts  

• Partner with Sales, Product, and Support to close feedback loops and improve customer outcomes  

• Standardize playbooks for onboarding, adoption, renewal, and expansion  

• Use data to identify growth opportunities and optimize account strategies  

• Build dashboards and reporting that create visibility into retention performance and risks  

• Elevate customer conversations from reactive support to strategic partnership  

• Drive operational rigor—clean data, disciplined forecasting, and consistent execution 

• Stay ahead of the curve on AI tooling, agentic workflows, and CS technology bringing emerging capability into the team before it becomes standard practice 
• Develop and iterate enterprise-grade engagement models that account for complex stakeholder environments, multi-site deployments, and long contract cycles 

• Stay ahead of the curve on AI tooling, agentic workflows, and CS technology bringing emerging capability into the team before it becomes standard practice 
• Develop and iterate enterprise-grade engagement models that account for complex stakeholder environments, multi-site deployments, and long contract cycles 

What You'll Bring: 

• 8+ years in Customer Success, Account Management, or Renewals in B2B SaaS  

• 3+ years leading managers and scaling customer-facing teams  

• Proven ownership of retention metrics (NRR, GRR, churn reduction)  

• Experience managing mid-market or scaled customer segments  

• Strong commercial instincts—comfortable driving renewals, upsells, and expansion  

• Ability to design systems, not just manage people  

• AI fluency—experience using AI tools for forecasting, customer insights, or workflow automation  

• Skilled at translating data into action and executive-level narratives  

• Strong cross-functional leadership—able to influence without authority  

• Clear communicator who can simplify complexity and drive alignment  

• High ownership mindset—you see gaps and close them fast 

• Genuine curiosity about how AI and automation are reshaping customer success;  you experiment, you test, and you bring what works back to the team 
• Experience managing enterprise or upper mid-market SaaS accounts with complex buying committees, procurement cycles, and multi-year contract structures 
• A track record of building in ambiguity, you don't wait for perfect data or a defined playbook to take action 
• Hands-on familiarity with AI tools across the CS stack, from health scoring models to LLM-powered customer insights to automated renewal workflows  

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. 

Role Summary: 

As our Lead Full Stack Software Engineer, you will own the future of how OfficeSpace builds, hosts, monitors, and deploys AI features, from Chatbots to Customer facing MCP Servers to Autonymous agents that handle day to day facilities management tasks. 

We move fast. We expect precision. And we trust you to own outcomes. 

What You’ll Do: 

• Lead the architecture and production evolution of OfficeSpace’s AI platform. 

• Design and operate Python-based AI services that integrate deeply with our Ruby on Rails backend and React frontend. 

• Partner with our Devops team to define best practices for deploying and hosting AI agents 

• Act as the technical owner for AI reliability—defining guardrails, observability, testing strategies, and failure modes for AI-driven functionality. 

• Build and evolve full-stack systems with a long-term mindset—maintainable code, extensible architectures, and clean interfaces. 

• Define and drive performance benchmarks across AI systems, using metrics, profiling, and load testing to improve latency, throughput, and stability. 

• Design and operate cloud-native, data-intensive systems using GCP, BigQuery, and Kafka to power event-driven and AI-enabled workflows. 

• Embed quality early—shift-left testing, observability, and validation to ensure predictable, enterprise-ready releases. 

• Proactively address security, data integrity, and technical debt—especially where AI intersects with customer data and core workflows. 

• Partner with senior engineers and architects to evaluate designs, align on tradeoffs, and move the system forward. 

• Mentor engineers through thoughtful code reviews and technical guidance, with room to step into formal people leadership over time. 

What You Bring: 

• 7+ years building and evolving production web applications, with demonstrated ownership of complex systems and technical direction. 

• Strong backend experience (Python or Ruby on Rails preferred; Java, Node.js, or Go welcome) and modern frontend development (React preferred). 

• Hands-on experience shipping AI-driven features in production—LLM-based systems, automation workflows, or agentic patterns—with an emphasis on safety, observability, and maintainability. 

• Deep understanding of cloud-native systems (GCP preferred), data platforms (BigQuery), and event-driven architectures (Kafka). 

• Proven ability to design for enterprise-scale performance, reliability, and security. 

• Comfort operating as a technical leader—navigating differing opinions, driving alignment, and mentoring peers. 

• A builder’s mindset. You move with urgency, think long-term, and take ownership from idea to impact. 

• An early adopter’s curiosity for agentic AI—and the discipline to ship it responsibly. 

Role Summary:

As a Senior Full-Stack Software Engineer at OfficeSpace, you will play a pivotal role in designing, developing, and optimizing innovative software solutions. Your work will directly contribute to a high-performance, AI-driven technology environment, focusing on using Ruby on Rails for backend development and React for frontend development to deliver scalable, user-focused applications.

What You’ll Do:

• Full-Stack Development:  Develop and enhance applications using Ruby on Rails and React. Focus on creating scalable and maintainable solutions with user-centric designs.
• Drive High-Impact Solutions:  Contribute to the development and maintenance of solutions emphasizing performance, reliability, and maintainability. Work with technologies like Google Cloud Platform and BigQuery for efficient data management and analytics.
• AI & Data-Driven Innovation: Leverage AI-powered tools to streamline processes, improve user experiences, and enhance development workflows.
• End-to-End Ownership & Quality Shift-Left: Collaborate on code quality, applying test-driven development and embedding quality checks throughout the development process.
• Performance Optimization: Assist in identifying and resolving performance bottlenecks to enhance speed and reliability.
• Security & Technical Integrity: Proactively address security concerns and contribute to maintaining a high standard of code integrity.
• Collaborative Development: Work closely with team members, including junior engineers, to share knowledge, provide constructive code reviews, and implement best practices.

What You’ll Bring:

• Technical Expertise: 5+ years of full-stack development experience, with strong proficiency in Ruby on Rails and React..
• API Development: Familiarity with GraphQL or RESTful API design and implementation.
• Cloud and Data: Exposure to cloud technologies like Google Cloud Platform and experience with databases such as MariaDB or NoSQL systems (e.g., Redis, Elasticsearch).
• Performance Optimization: Understanding of application performance metrics and strategies for improvement.
• AI & Automation: Familiarity with AI tools to automate tasks and improve efficiency.
• Team Collaboration: Demonstrated ability to collaborate within agile teams, working closely with product managers and designers to deliver high-quality solutions.
• Mentorship: Some experience mentoring junior developers is a plus.

Role Summary: 

You shape how teams experience the modern workplace. As a Senior Product Designer at OfficeSpace, you own design end to end for a major areas of the platform — translating complex workplace workflows into clear, scalable experiences that customers trust every day. You set design direction alongside Product Managers and Engineers, raise the bar on craft and consistency, evolve our design system, and use AI to move from exploration to shipped impact at rapid speed.  

What You’ll Do: 

• Translate user needs and product requirements into simple, intuitive experiences across the platform. 

• Drive design work end- to- end—from exploration and prototyping to polished, production-ready solutions. 

• Partner closely with Engineers to ensure designs are usable, accessible, and technically feasible. 

• Contribute to and evolve our Figma-based design system, including components, patterns, and documentation. 

• Support discovery through research sessions, rapid prototypes, and iterative validation. 

• Use AI tools to accelerate ideation, generate design variations, and streamline repetitive design tasks. 

• Champion accessibility and inclusive design across workflows and interfaces. 

• Raise consistency and craft across the full product experience. 

• Incorporate feedback quickly — balancing speed, quality, and clarity as we ship. 

• Review adoption metrics and post-production feedback (i.e. NPS, CSAT) to propose refinement and enhancements that drive positive user sentiments and product adoption 

• Elevate the design practice—mentoring peers and sharing best practices to help set the bar for what great looks like at OfficeSpace. 

What You Bring: 

• 3–5 years of experience in Product Design, UI/UX, or a related field—ideally in SaaS or enterprise products. 

• Strong visual, interaction, and systems-thinking skills with attention to detail. 

• Proficiency in Figma and comfort working within component-based design systems. 

• Experience collaborating closely with Product Managers and Engineers on complex workflows. 

• Curiosity and confidence using AI tools to improve speed, exploration, and design quality. 

• A portfolio that demonstrates user-centered thinking and shipped product work. 

• Working knowledge of WCAG standards and accessible design practices. 

• Clear communicator — can explain design decisions with confidence and clarity. 

• Growth mindset. Can iterate quickly, seek receptive feedback, and take shared ownership of outcomes. 

• Demonstrated ability to navigate ambiguity — scoping problems, framing trade-offs, and driving alignment across teams 

Role Summary: 

• You will shape the technical future of OfficeSpace. 

• As our Principal Software Engineer (Ruby/React), you don’t just ship features—you architect systems that scale globally. You lead with clarity. You raise the bar. You design resilient, internet-scale applications that power the modern hybrid workplace. 

• We provide the platform. You drive the vision. 

What You’ll Do: 

• Architect and evolve internet-scale systems with performance, reliability, and scalability as first principles. 

• Lead the technical direction for Ruby on Rails and React applications across the platform. 

• Design clean, extensible APIs and modern front-end architectures that deliver fast, intuitive user experiences. 

• Orchestrate AI-assisted development workflows—using AI agents to accelerate code scaffolding, documentation, test generation, refactoring, and dependency analysis. 

• Own architectural decisions across services, databases, and infrastructure—including MariaDB, Redis, and Elasticsearch. 

• Use Kubernetes to scale Rails applications to handle Enterprise traffic 

• Guide multiple high-impact initiatives in parallel, ensuring secure, well-tested, production-ready releases. 

• Mentor engineers to think in systems, write maintainable code, and leverage AI responsibly to increase velocity without sacrificing quality. 

• Proactively identify technical debt and scalability risks—and drive pragmatic solutions before they become bottlenecks. 

• Partner with Product, Design, and Leadership to evaluate trade-offs and deliver exceptional experiences across browsers and devices. 

• Continuously evaluate emerging technologies—including AI tooling—to strengthen platform performance and team effectiveness. 

What You Bring: 

• 10+ years of backend engineering experience, with deep expertise in Ruby on Rails. 

• 10+ years of experience building modern front-end applications with JavaScript (ES6+) and React. 

• Proven experience designing and scaling relational databases (MariaDB) and working with Redis and Elasticsearch. 

• Demonstrated ability to define and influence architectural direction across large systems. 

• Experience leading engineers through complex technical decisions while fostering a culture of trust and high standards. 

• Hands-on experience with GraphQL (preferred). 

• Experience integrating AI development tools (e.g., code generation, static analysis, automated testing assistants) into engineering workflows. 

• Strong judgment—knowing when to automate, when to refactor, and when to rethink from first principles. 

• Clear communicator who can translate technical complexity into practical decisions. 

Role Summary: 

The companies that define the next decade will be the ones who learned to move faster, decide smarter, and execute with precision—AI at the core. OfficeSpace Software is building that company now, and the Executive Chief of Staff is how we get there. 

In this role, you will sit at the intersection of strategy, transformation, and execution—partnering directly with our CEO and Executive Leadership Team to drive the initiatives that accelerate growth, unlock efficiency, and shape the future of work. You will own the cross-functional operating rhythm that keeps the business moving, and you will do it with the judgment and discretion that comes from being trusted with things that matter.  

This is high-speed, high-visibility, and high-impact—and it demands someone who can take a complex problem, drive it independently through to a decision, and return with a clear output. If that’s the environment where you do your best work, we want to meet you. 

What You’ll Do 

Independent Initiative Ownership 

• Own high-impact strategic initiatives end-to-end—from scoping and alignment through execution and measurable business results. You drive the work, not the calendar. 

• Translate executive priorities into clear, AI-enabled execution plans across functions—with the autonomy to make calls and move without constant direction. 

• Identify execution risks early and deploy mitigation strategies using predictive insights and scenario modeling. Surface what matters; resolve what you can before it lands on the CEO’s desk. 

• Design and track KPIs that tie initiatives directly to revenue, efficiency, and profitability—owning the accountability loop, not just the reporting layer. 

Operating Cadence & Cross-Functional Execution 

• Own and drive the company’s cross-functional operating cadence—QBRs, executive rhythms, leadership forums, and the connective tissue that keeps a fast-moving business aligned and accountable. 

• Orchestrate cross-functional teams to deliver faster, with tighter feedback loops and real-time visibility. You are the force multiplier that unblocks decisions and moves work forward. 

• Build AI-powered operating systems—dashboards, copilots, workflows—that increase the speed and quality of decision-making across the ELT. 

Executive Partnership & Storytelling 

• Partner with the ELT to prepare board materials, CEO updates, and investor narratives using AI-assisted synthesis—turning complex data and dynamics into clear, high-stakes communications. 

• Support the storytelling of the business in a transformative year of AI-native product and company evolution. Help the CEO communicate with clarity, credibility, and confidence internally and externally. 

Change Management & Organizational Navigation 

• Act as a trusted partner to the CEO through periods of organizational change—helping design, sequence, and land transformational decisions in ways that stick. 

• Help the ELT navigate the human side of change: communication, sequencing, stakeholder alignment, and the difference between a decision that’s made and one that’s actually adopted. 

• Serve as a connective bridge across functions—building trust with leaders, surfacing misalignments before they become problems, and modeling the operating culture the company is building toward. 

Judgment, Discretion & Confidentiality 

• Exercise exceptional judgment about what to act on, what to escalate, and what to hold—recognizing that proximity to sensitive information is a trust, not a tool. 

• Handle commercially sensitive data, executive dynamics, personnel decisions, and investor-level information with the discretion expected of someone operating at the most senior level of the organization. 

• Know when to be visible and when to work quietly behind the scenes. Influence without overstepping. Move without leaving a wake. 

What You’ll Bring 

• 5–7 years in strategy consulting, SaaS operations, private equity value creation, or similar high-intensity environments—with a track record of owning outcomes, not just supporting them. 

• Demonstrated ability to take complex, ambiguous workstreams from problem definition through to a clear decision or output—independently, without requiring structure to be built around you. 

• Exceptional judgment: you know what to escalate, what to resolve, and what to hold in confidence. You’ve earned trust by being the person who handles sensitive situations with maturity. 

• Change management experience—you understand that transformation is as much about people and sequencing as it is about strategy. You’ve helped organizations navigate hard decisions, not just document them. 

• Strong operator mindset—you advise and execute, owning outcomes end-to-end. Coordination and synthesis are the floor, not the ceiling. 

• High AI fluency—experience using GenAI, automation tools, and data systems to accelerate workflows and insights. You build with AI, not just use it. 

• Sharp analytical thinking—you translate data into clear decisions and action, and you can hold a financial model, a SaaS metric, and an executive narrative in your head at the same time. 

• Executive presence—you communicate with clarity, influence senior stakeholders, and build trust quickly, even when you’re the least experienced person in the room. 

• Strong financial and SaaS metric literacy—you understand how decisions impact ARR, NRR, EBITDA, and the Rule of 40, not just in theory but in context. 

• A “Love to Win” attitude—you operate from a desire to see success, not a fear of failure. You bring pace, optimism, and resilience to hard problems. 

• Comfort in ambiguity—you bring structure, speed, and focus to complex problems, and you don’t wait to be told what to do next.