Insight Assurance
Cybersecurity
HeadofSales
Neural analysis suggests this role is
optimal for Senior candidates.
“Head of Sales at Insight Assurance. Skills: Revenue generation, Sales leadership, Player/coach role. Lead sales team. Develop sales team”
What You'll Achieve.
Revenue generation; Hit personal quota; Exceed personal quota; Grow GTM team
Industry & Context.
Deal strategy
What They're Looking For.
Must Have
5+ years B2B SaaS sales, 2+ years sales leadership, 2+ years player/coach role, Proven track record hitting quota, Managing a team experience, HubSpot proficiency
Nice to Have
Experience in compliance, Experience in cybersecurity, Experience in GRC, Building sales motion experience, Familiarity with channel GTM, Familiarity with partner-led GTM, Managing international teams, EU territory management, Early-stage company experience, Growth-stage company experience
What You'll Do.
Conduct pipeline reviews
Ensure performance accountability
Install self-sourcing culture
Build onboarding plans
Operate as player/coach
Carry $100k/quarter quota
Support complex opportunities
Cover strategic accounts
Enforce sales process
Define pipeline health
Collaborate with Partner Managers
Maximise partner pipeline
Maintain forecasting accuracy
Support EU territory build
Work with country managers
Support pipeline strategy
How You'll Work.
Team & Collaboration
Cross-functional teams; Work with marketing; Collaborate with CRO; Collaborate with Partner Managers; Work with country managers
Communication Scope
Deal intelligence reporting
Process & Methodology
Roadmap planning
Full Job Description
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 d
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