[Hiring] Head of Outbound Sales @iSpeedToLead

Role Description

We're looking for a Head of Outbound Sales to build and scale iSpeedToLead's outbound motion from zero, with a focus on large accounts, multi-seat deals, and annual contracts. You'll define the target account list, close the first deals yourself, build the playbook, and then hire and lead the team behind it. This role exists to turn outbound into a predictable revenue engine with a clear target - $250K/month in outbound-driven revenue within 6 months.

• 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

Qualifications

• 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

Requirements

• Bonus if you have:
• 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

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