ispeedtolead - Head of Outbound Sales
Requirements
• Experience in Real Estate, PropTech, lead generation, marketplaces, or performance-based sales • Experience selling to US real estate operators, wholesalers, investors, agents, or cash buyers • Experience building outbound teams and hiring SDRs, AEs, or outbound operators • Experience using conferences, sponsorships, gifting, or offline channels as part of an ABM motion • Experience selling annual contracts, multi-seat packages, or high-LTV B2B products
Responsibilities
• Build the outbound sales motion from scratch - target accounts, messaging, sequences, qualification criteria, sales process, and reporting • Define and prioritize the account list for large-account acquisition, including account scoring, tiering, territory logic, and buying-committee mapping • Run 1:1 and 1:few ABM campaigns across email, phone, LinkedIn, events, direct mail, and trigger-based outreach • Close the first enterprise and large-account deals yourself, including multi-stakeholder calls, negotiation, mutual action plans, and annual contracts • Use AI and sales tools to improve research, enrichment, signal tracking, outreach drafting, personalization, and conversion by stage • Work closely with leadership, marketing, product, and customer-facing teams to turn customer proof, case studies, and product value into strong outbound messaging • Hire, train, and lead the outbound team once the playbook is working and ready to scale • What Makes You a Strong Fit: • 7+ years of B2B sales experience, including experience closing enterprise or large-account contracts • Proven experience closing six-figure deals with multiple stakeholders, such as CROs, COOs, founders, owners, or senior operators • Strong hands-on experience with ABM - account research, account tiering, multi-threading, buying-committee mapping, and personalized outbound • Experience building outbound sales systems from zero, not only operating inside an existing process • Strong understanding of sales methodology such as MEDDIC, mutual action plans, structured discovery, qualification, and deal strategy • Confident with modern sales and AI tools such as Clay, Apollo, Cognism, UserGems, Smartlead, Outreach, Salesloft, Gong, AI voice agents, or similar tools • Fluent English, used daily for executive-level calls, negotiation, written outreach, internal communication, and sales documentation
Benefits
• You'll work at the core of a product-led, AI-powered startup where data drives every decision • Your work will ship fast and impact thousands of users • High autonomy, low bureaucracy: we trust you to own your domain • Remote-first culture with flexible hours and async-friendly communication • Salary (fixed base) ABOVE the market average • A smart, passionate team that moves fast, supports each other, and builds cool stuff • 15 paid vacation days plus 5 paid sick days annually • Paid access to courses, books, and growth resources • Real decision-making power and ownership of your results
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