Head of Outbound Sales

ISpeedToLead Inc.; Madrid; On-site; EUR 90,000 - 140,000; Full time

Benefits offered by this job

Remote-first culture

Flexible hours

Async-friendly communication

Salary above market average

15+5 vacation/ sick days

Job summary

iSpeedToLead is seeking a Head of Outbound Sales to build and scale its outbound motion from zero, targeting large accounts and annual contracts. You will define the target list, close initial six-figure deals, create the playbook, and hire the team to scale.

The role emphasizes using AI tools to enhance outreach and conversion. Expect to develop a strategic outbound engine, drive multi-channel campaigns, and collaborate with product, marketing, and leadership to turn customer proof into

Qualifications

• 7+ years in B2B sales, including enterprise or large-account closes.
• Proven track record closing six-figure deals with multiple stakeholders.
• Hands-on ABM with multi-threading and account-tiering.
• Experience building outbound systems from zero, not just executing existing processes.
• Strong knowledge of MEDDIC and deal strategy.

Responsibilities

• Build the outbound motion from scratch: target accounts, messaging, sequences, and reporting.
• Define account lists for large-account acquisition and map buying committees.
• Run ABM campaigns across email, phone, LinkedIn, events, and direct mail.
• Close first enterprise deals with multi-stakeholder calls and annual contracts.
• Use AI and sales tools to improve research, outreach, personalization, and conversions.
• Collaborate with leadership, marketing, product, and customer-facing teams to craft compelling messaging.
• Hire, train, and lead the outbound team once the playbook is scalable.

Skills

B2B sales

Enterprise deals

ABM

MEDDIC

Sales tooling

Fluent English

Leadership

Tools

Clay

Apollo

Cognism

UserGems

Smartlead

Outreach

Salesloft

Gong

Job description

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