Head of Outbound Sales

About The Company
Turning marketing into a market-domination weapon, we created a new category - the marketplace for future customers. Businesses shop for leads as they shop for products in e-commerce: you see everything about a lead before you buy - full transparency, control, and predictable outcomes. We're the #1 lead marketplace in the USA, and we're accelerating.
Role Overview
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.
What You'll Be Doing:
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
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
Why You'll Love It Here:
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

Work arrangement
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