Head of Sales - US Remote

Insight Assurance is a global audit firm on a mission to transform how organizations achieve cybersecurity and compliance. Founded by former Big 4 (EY) professionals, we deliver next-generation audit services across SOC 2, ISO 27001, PCI DSS (QSA), HITRUST, CMMC (C3PAO), and FedRAMP (3PAO) frameworks.

We're not your traditional audit firm --- we're tech-enabled, leveraging compliance automation and advanced collaboration tools to make audits faster, smarter, and more impactful for our clients. Recognized on the Inc. 5000 and Fast 50 lists, Insight Assurance is one of the fastest-growing global audit firms, with 170+ professionals supporting nearly 2,000 clients across the Americas, EMEA, and APAC.

The Opportunity

We are growing fast and building the GTM team to match. As our first dedicated Head of Sales, you will be the person who turns a high-performing but loosely structured sales team into a disciplined, accountable revenue machine.

This is a player/coach role. You will carry a personal quota, work live deals, and be in the trenches with the team every day --- while also owning the culture, structure, and accountability that makes the whole GTM motion work. You will report directly to the CRO and have an immediate impact on how we grow.

What You'll Do

Lead and develop the sales team

• Manage a team of Strategic AEs and a Junior AE across domestic and EU territories
• Own coaching, pipeline reviews, deal strategy, and performance accountability
• Install a self-sourcing culture --- every AE is expected to source, not just close
• Build structured onboarding and ramp plans for new AE hires

Carry a personal quota

• Operate as a player/coach --- carry $100k/quarter personal quota
• Work live deals, support complex opportunities, and cover strategic accounts during team transitions
• Stay close to the market and bring real deal intelligence back to the team

Own the sales motion

• Define and enforce a consistent sales process from discovery through close
• Work with marketing to align on MQL definition, lead quality, and pipeline health
• Collaborate with the CRO and Partner Managers to maximise partner-sourced pipeline
• Maintain clean CRM hygiene and accurate forecasting in HubSpot

Drive geo execution

• Support EU territory build alongside the London-based Strategic AE
• Work with country managers in APAC and LATAM on deal support and pipeline strategy

What We're Looking For

Must have

• 5+ years in B2B SaaS or professional services sales, with at least 2 years in a sales leadership or player/coach role
• Proven track record of hitting and exceeding personal quota while managing a team
• Experience in compliance, cybersecurity, GRC, or adjacent markets --- you understand the buyer and the conversation
• Strong coaching instincts --- you make the people around you better
• Data-driven --- you run your team on pipeline metrics, not gut feel
• HubSpot proficiency or equivalent CRM experience

Strong plus

• Experience building or scaling a direct sales motion from a partner-heavy baseline
• Familiarity with channel and partner-led GTM models
• Experience managing internationally distributed teams or EU territory
• Early-stage or growth-stage company experience --- you know how to operate without perfect infrastructure

What We Offer

• Equity participation
• Remote-first --- work from anywhere in the US
• Direct line to the CRO and meaningful influence on GTM strategy
• A team that is already performing --- you are here to elevate it, not rebuild from zero
• Fast-moving, low-bureaucracy environment where decisions get made, and things get done
• PTO and National Holidays

Privacy Notice

Insight Assurance is committed to data privacy. We use Greenhouse for recruitment, and your data is processed securely. We do not sell personal information. For full details regarding CCPA and GDPR rights, please contact [email protected].