Head of GTM & Enterprise Sales — Remote + Equity

Secure Engage; Oregon (WI); Hybrid; USD 180,000 - 300,000; Full time

Benefits offered by this job

Remote-first flexibility

Equity and commissions

Paid time off and incentives

GTM playbook autonomy

Mission-driven team

Job summary

Secure Engage is seeking a Head of Sales / Go-To-Market to lead North America sales, shaping the GTM strategy and building a high-performance team. This role focuses on enterprise deals across regulated sectors and emphasizes social selling, compelling messaging, and strong cross-functional collaboration.

The candidate will partner with the CEO and product team to craft offers, ensure regulatory-aligned positioning, and drive outbound/inbound growth in a fast-paced, hybrid/remote setup across

Qualifications

• 8+ years of experience in B2B SaaS sales, startup or high-growth background.
• Proven ability to close enterprise deals and build repeatable sales engines.
• Strong storytelling, presentation, and negotiation skills.

Responsibilities

• Own and execute the overall sales and go-to-market strategy for North America.
• Build and lead a high-performance sales team targeting enterprise clients (banks, insurers, law firms, regulators).
• Develop playbooks, pipeline management processes, and scalable outbound/inbound strategies.
• Work with CEO and product team to shape offers, messaging, and compliance-focused positioning.
• Leverage social selling, webinars, and personal branding to drive visibility and conversions in legaltech, fintech, cyber risk.
• Partner with marketing to align brand narrative and channel engagement.
• Cultivate long-term relationships with decision-makers in compliance, legal, and procurement functions.

Skills

B2B SaaS sales

Enterprise deals

Social selling (LinkedIn)

Storytelling & presentations

Negotiation skills

Fast-paced environment

Job description

Secure Engage is seeking a Head of Sales / Go-To-Market to lead North America sales, shaping the GTM strategy and building a high-performance team. This role focuses on enterprise deals across regulated sectors and emphasizes social selling, compelling messaging, and strong cross-functional collaboration.

The candidate will partner with the CEO and product team to craft offers, ensure regulatory-aligned positioning, and drive outbound/inbound growth in a fast-paced, hybrid/remote setup across