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 CCPA: 

• Insight Assurance shares your personal data/information with Greenhouse recruiting because this is the tool we use for the recruitment process.
• Insight Assurance does not sell personal data/information under any circumstances.
• You may exercise your rights under personal data protection legislation by reaching out to us via: HR@insightassurance.com or submit a request via mail at 400 N Tampa St. 15th Floor Suite 122, Tampa, FL 33602

Privacy Notice GDPR:

This notice informs you about the categories of Personal Data/ Information and the Purpose and Scope of Processing Activities to be undertaken by Insight Assurance (we, us, our), under its job application and recruitment process.

We resort to Greenhouse.com as the platform that supports our recruitment process, and therefore your Personal Data/ Information will be Processed on this tool (hosted, shared with, cross-referenced, accessed by our team); we have in place contractual terms and the commitment of Greenhouse.com that ensures the Security and Confidentiality plus Purpose limitation with regards to the Processing of your Personal Data.

When you reply to one of your job postings, you voluntarily and freely submit your Personal Data to us; this, allied with the fact that the Processing by us (and over Greenhouse.com) of that Personal Data has the sole Purpose of validating your application and proceeding with the inherent scrutiny and decision, allows us to argue having Legitimate Interest as the applicable Legal Basis to undertake the Processing of your Personal Data under this scope.

We are a U.S. based company, hence some or all Personal Data pertaining to you will be hosted in the U.S.

The categories of Personal Data under Processing consist of:

• Identification
• Contact
• Education and Professional
• Interview performance
• Evaluation

You may exercise several Rights as determined under applicable Personal Data Protection legislation, in short:

• Right of Access – meaning getting information about the Personal Data under Processing by us, except for the information you already know;
• Right of Erasure – you may ask for us to erase all Personal Data pertaining to you under Processing; this may imply you being excluded from the recruitment process, for without information we cannot proceed with it;
• Right of Opposition or Restriction of Processing – you may ask us to stop some Processing or restrict the Processing of some Personal Data, this may imply you being excluded from the recruitment process, at our sole discretion also for without information we cannot proceed with it;
• Rectification – you can rectify your Personal Data at anytime