Head of Sales - US Remote

Insight Assurance

1d•Remote

About The Position

Insight Assurance is a global audit firm focused on transforming cybersecurity and compliance. Founded by former Big 4 professionals, the firm offers services in SOC 2, ISO 27001, PCI DSS, HITRUST, CMMC, and FedRAMP. They utilize technology to enhance audit efficiency and impact. Recognized for rapid growth, Insight Assurance has over 170 professionals serving nearly 2,000 clients globally. This role is for the first dedicated Head of Sales, responsible for structuring and leading a high-performing sales team. It's a player/coach position where the individual will manage a personal quota, work on live deals, and guide the team's culture, structure, and accountability. The Head of Sales will report directly to the CRO and play a key role in the company's growth strategy.

Requirements

5+ years in B2B SaaS or professional services sales.
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.
Strong coaching instincts.
Data-driven approach to sales management, focusing on pipeline metrics.
HubSpot proficiency or equivalent CRM experience.

Nice To Haves

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.

Responsibilities

Lead and develop the sales team, managing Strategic AEs and a Junior AE across domestic and EU territories.
Own coaching, pipeline reviews, deal strategy, and performance accountability for the sales team.
Install a self-sourcing culture, ensuring every AE is responsible for sourcing leads.
Build structured onboarding and ramp plans for new AE hires.
Carry a personal quota of $100k per quarter.
Operate as a player/coach, working live deals, supporting complex opportunities, and covering strategic accounts during team transitions.
Gather market intelligence and share deal insights with the team.
Define and enforce a consistent sales process from discovery through close.
Collaborate with marketing to align on MQL definition, lead quality, and pipeline health.
Work with the CRO and Partner Managers to maximize partner-sourced pipeline.
Maintain CRM hygiene and accurate forecasting in HubSpot.
Support EU territory development alongside the London-based Strategic AE.
Assist country managers in APAC and LATAM with deal support and pipeline strategy.