[Remote] Head of Outbound Sales

Note The job is a remote job and is open to candidates in USA. iSpeedToLead is a lead marketplace that provides businesses with transparent access to future customers and is accelerating its growth in the USA. The Head of Outbound Sales will build and scale the company’s outbound sales motion from zero, personally close initial enterprise deals, develop the sales playbook, and hire and lead the team toward predictable outbound revenue. 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 11 and 1few 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 Skills 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 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 Remote-first culture with flexible hours and async-friendly communication 15 paid vacation days plus 5 paid sick days annually Paid access to courses, books, and growth resources High autonomy, low bureaucracy we trust you to own your domain Real decision-making power and ownership of your results Company Overview iSpeedToLead is Instant motivated seller lead marketplace. It was founded in 2021, and is headquartered in Boston, Massachusetts, USA, with a workforce of 51-200 employees. Its website is https//ispeedtolead.com.