Head of Outbound Sales

Join iSpeedToLead, an innovative company revolutionizing marketing by creating the leading marketplace for future customers. Our platform empowers businesses to purchase leads with transparency, control, and predictable results, similar to e-commerce. As the top lead marketplace in the USA, we are expanding rapidly and seeking a Head of Outbound Sales to build and scale our outbound sales efforts from the ground up. This role focuses on acquiring large accounts, managing multi-seat deals, and securing annual contracts.

Key Responsibilities
Develop the entire outbound sales process, including target account identification, messaging, sequences, qualification criteria, sales workflows, and reporting. Define and prioritize a target account list for large-account acquisition, incorporating account scoring, tiering, territory logic, and buying-committee mapping. Execute personalized Account-Based Marketing (ABM) campaigns across multiple channels such as email, phone, LinkedIn, events, direct mail, and trigger-based outreach. Personally close initial enterprise and large-account deals by managing multi-stakeholder calls, negotiations, mutual action plans, and annual contract agreements. Utilize AI and sales tools to enhance research, data enrichment, signal tracking, outreach drafting, personalization, and improve conversion rates at each stage. Collaborate closely with leadership, marketing, product, and customer-facing teams to translate customer success stories and product value into compelling outbound messaging. Once the sales playbook is established, hire, train, and lead the outbound sales team to scale operations effectively.

Required Qualifications
A minimum of 7 years in B2B sales with a proven track record of closing enterprise or large-account contracts. Demonstrated success in securing six-figure deals involving multiple stakeholders such as CROs, COOs, founders, owners, or senior operators. Strong hands-on experience with ABM strategies, including account research, tiering, multi-threading, buying-committee mapping, and personalized outbound outreach. Experience building outbound sales systems from scratch rather than working within existing processes. Solid understanding of sales methodologies such as MEDDIC, mutual action plans, structured discovery, qualification, and deal strategy. Proficiency with modern sales and AI tools including Clay, Apollo, Cognism, UserGems, Smartlead, Outreach, Salesloft, Gong, and AI voice agents. Fluent English communication skills, capable of handling executive-level calls, negotiations, written outreach, internal communications, and sales documentation.

Preferred Qualifications and Benefits
Experience in Real Estate, PropTech, lead generation, marketplaces, or performance-based sales is highly valued. Familiarity with selling to US real estate operators, wholesalers, investors, agents, or cash buyers is a plus. Proven ability to build outbound teams and hire SDRs, AEs, or outbound operators. Experience leveraging conferences, sponsorships, gifting, or offline channels as part of ABM strategies. Background in selling annual contracts, multi-seat packages, or high-LTV B2B products is advantageous.

At iSpeedToLead, you will be part of a product-led, AI-powered startup where data drives every decision. The environment is fast-paced, with your contributions impacting thousands of users. Enjoy high autonomy with minimal bureaucracy and ownership over your domain. We embrace a remote-first culture with flexible hours and asynchronous communication. Compensation is competitive and above market average. You will collaborate with a smart, passionate team that moves quickly, supports one another, and builds innovative solutions. Benefits include 15 paid vacation days, 5 paid sick days annually, and access to paid courses, books, and growth resources to support your professional development. This role offers real decision-making power and ownership of your results.

This is a unique opportunity to lead outbound sales at a rapidly growing company with a clear revenue target of $250K per month within six months. If you are a strategic, hands-on sales leader ready to build and scale a high-impact outbound sales engine, we encourage you to apply.