Senior Director - Demand Generation

Inside Real Estate powers over 400,000 real estate agents, teams, and brokerages through BoldTrail — a platform that brings front office, back office, and AI tools together in one place. We’re one of the fastest-growing companies in proptech, and we’re building the marketing function to match.

The Role

This is a pivotal role on our marketing leadership team — with a performance + continued transformation mandate, not a maintenance job. You’ll own the demand generation engine — the strategy, the budget, the team, and the outcomes — and be directly accountable for driving qualified pipeline across our SMB, mid-market, and enterprise segments.

The landscape has shifted. Buyers find tech partners differently now. AI is changing how teams operate. The right person for this role sees that clearly, is excited by the moment and knows how to build for it — not as a headline, but as a genuine operating shift. You’ll report to the CMO, work in proximity to a talented and visionary CEO and ELT and work in close partnership with Sales and Business Development to ensure marketing and pipeline motions run as one.

What You’ll Own

• Demand generation strategy across all segments — lead targets, CPL, pipeline coverage, and MQL-to-SQL conversion
• All paid media — Google, LinkedIn, Meta, Microsoft, and performance partnerships — with full budget accountability, including emerging channels worth testing
• Visibility in AI-powered search environments — AEO, GEO, and the evolving ways buyers discover and evaluate vendors
• Agentic and AI-native demand programs — not as experiments, but as real pipeline motions
• HubSpot and marketing technology — lead scoring, nurture programs, audience segmentation, and deliverability
• A talented demand gen team — and the willingness to transform how it operates, not just manage it as-is
• Executive-level reporting — a clear, consistent view of what’s working, what isn’t, and what to do about it
• Tight alignment with our Business Development team — shared ICP definition, shared pipeline standards, and a closed feedback loop on lead quality

What We’re Looking For

• 8+ years in demand generation with at least 3 in a senior leadership role owning strategy, budget, and team
• A track record of driving ICP-qualified pipeline in B2B SaaS — across multiple segments, not just one
• Deep hands-on experience with paid media at scale — you’ve managed significant budgets and can show the results
• Real AI fluency — not familiarity with tools, but a genuine rethinking of how demand gen works: agentic funnels, AI-optimized content surfaces, AI-driven team efficiency. You’ve done it, not just read about it
• Genuine curiosity about the product and the sales message — you want to understand what actually moves customers, not just optimize top-of-funnel metrics
• A track record of driving real transformation in teams and processes — the kind that required uncomfortable change, not just incremental improvement
• HubSpot fluency — not just as a user, but as someone who builds the architecture others rely on
• Strong cross-functional instincts — you know how to work with Sales without stepping on toes, and how to push back without burning bridges

Real estate or proptech experience is a plus, but not a requirement.

Why Inside Real Estate

• Real ownership — budget, strategy, team, and a seat at the leadership table
• A CMO who is actively building a modern marketing organization and wants a genuine thought partner
• A product that real estate professionals actually love — 400,000+ customers and growing
• A team that’s talented, motivated, and ready to be led — and pushed in transformation

We offer a competitive total rewards package including:

• Competitive salary
• 3 Medical plans to choose from - 1 PPO and 2 HDHPs
• 2 Dental plans to choose from
• Vision
• HSA - company-funded
• FSAs - healthcare, limited purpose, dependent care
• Short-Term Disability - company-paid
• Long-Term Disability - company-paid
• Basic Employee Life Insurance - company-paid
• Voluntary Dependent Life Insurance
• Voluntary Accident Insurance
• Voluntary Critical Illness
• Voluntary Hospital Indemnity
• ID Protection
• Pet Insurance
• 401(k) Retirement Savings with company match
• Paid PTO/Vacation/Sick Time
• 11 company-recognized holidays
• Company-paid Parental/Disability Leave

In addition, at IRE, we focus on driving top results providing:

• Opportunities to grow within our company;
• Potential to work in a remote setting;
• Exciting/energetic work environment and fun, creative culture.

IRE EEO Statement - We believe that the unique contributions of all Insiders are the driver of our success. To make sure that our products and culture continue to incorporate everyone's perspectives and experiences we never discriminate on the basis of race, religion, national origin, gender identity or expression, sexual orientation, age, marital, veteran, or disability status.