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