Director of Sales Development

Office Space 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.

Office Space is looking for a Director of Sales Development to build the next generation of our pipeline engine.

You will own inbound- and outbound-sourced pipeline across new-logo and expansion accounts, lead our strategic ABX motion, and develop SDRs and Senior SDRs into high-performing GTM talent. You'll shape how people and AI agents work together—using automation to expand capacity while keeping judgment, relationships, and buyer experience human-led.

This is a builder role. You'll partner closely with Sales, Marketing, Revenue Operations, Finance, and Enablement to turn revenue goals into a focused operating system that improves account penetration, conversion, pipeline productivity, and talent development as Office Space moves upmarket.

• Own the pipeline engine. Translate revenue targets, pipeline coverage, conversion rates, and productivity assumptions into SDR capacity, quotas, territories, coverage, and investment decisions.
• Build a high-performing team. Lead, coach, and develop SDRs and Senior SDRs against clear goals for pipeline, conversion, quality, productivity, and progression.
• Lead strategic ABX. Turn account segments, intent, buying-group signals, whitespace, and market triggers into focused action across Mid-Market and Enterprise new-logo and expansion accounts.
• Build depth in priority accounts. Establish disciplined account-planning motions across research, contact mapping, personalization, calling, and multi-channel engagement.
• Orchestrate people and AI. Decide which workflows AI agents should own, which should remain AI-assisted, and where human judgment creates the greatest advantage.
• Build and govern AI-enabled workflows. Deploy, test, measure, and improve agents supporting research, prioritization, buying-group mapping, personalization, follow-up, coaching, and pipeline intelligence.
• Turn AI into measurable capacity. Measure impact on opportunity creation, pipeline, conversion, velocity, productivity, buyer experience, and acquisition cost—not activity volume alone.
• Improve the full GTM funnel. Strengthen Marketing-to-SDR prioritization and SDR-to-Sales qualification, context transfer, acceptance, and conversion.
• Plan before adding headcount. Model tradeoffs across people, technology, AI agents, coverage, productivity, and conversion to identify the highest-leverage path to growth.
• Build operating discipline. Establish forecasting, performance reporting, quality controls, and cross-functional operating cadences with Finance and Revenue Operations.
• Coach in the work. Use calls, emails, account plans, qualification decisions, pipeline data, and AI-generated insights to make coaching specific and actionable.
• Build future GTM leaders. Strengthen Ascend and create measurable development paths from SDR to Senior SDR, closing roles, leadership, and other GTM careers.
• Raise the readiness bar. Build certifications around buyers, industries, messaging, qualification, ABX execution, AI-enabled selling, and responsible AI use.
• Shape the system as we scale. Continuously challenge where work happens, who—or what—should perform it, and how Office Space can generate more qualified pipeline without adding unnecessary complexity.

• Experience leading and transforming a B2B SaaS SDR or BDR organization.
• A track record of building account-based prospecting or ABX motions across Mid-Market and Enterprise accounts.
• Demonstrated success improving attainment, qualified pipeline, rep productivity, qualification quality, and downstream conversion.
• Strong capability in capacity planning, organizational design, forecasting, territory and coverage…