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.

Role Overview 

We're looking for an Enterprise Account Executive who knows how to win in complex, high-value sales environments. This is not a transactional role — it's a strategic, consultative position for a seasoned closer who thrives on long-cycle deals, multi-stakeholder buying committees, and building executive-level relationships that generate lasting revenue. 

As an Enterprise AE at Insight Assurance, you will own a portfolio of named enterprise accounts and greenfield enterprise opportunities across key verticals — including healthcare, financial services, technology, defense industrial base, and government contracting. You'll work directly with CISOs, CTOs, CFOs, and compliance leadership to position Insight Assurance's audit and certification services as strategic business assets, not just compliance checkboxes. 

You understand the compliance landscape — or you learn it fast. You can navigate a 12-month sales cycle with the same energy you bring to a 30-day close. And you know how to make a complex purchase feel inevitable. 

Key Responsibilities: 

Enterprise Pipeline & Revenue Ownership 

• Own a named account list and greenfield enterprise territory — developing and executing a disciplined account strategy that identifies, prioritizes, and penetrates high-value target organizations across assigned verticals. 

• Drive the full enterprise sales cycle from initial outreach through discovery, solution design, proposal, commercial negotiation, and close — managing complex, multi-stakeholder opportunities with precision and strategic focus. 

• Consistently achieve and exceed quarterly and annual revenue quotas, maintaining accurate pipeline forecasting and deal-stage discipline in CRM at all times. 

• Manage and grow a high-value pipeline through a combination of outbound prospecting, inbound qualification, executive referrals, partner channels, and industry event networking. 

• Negotiate enterprise-level Master Services Agreements (MSAs), Statements of Work (SOWs), and multi-year engagement contracts — with a clear understanding of commercial levers, pricing structures, and risk allocation. 
  
  

Executive Relationship Management 

• Build and sustain trusted advisor relationships with C-suite and VP-level decision-makers — including CISOs, CTOs, CFOs, General Counsel, and Heads of Compliance — across named accounts and active opportunities. 

• Develop deep familiarity with each enterprise client's organizational structure, business priorities, regulatory obligations, and security posture — using this understanding to position Insight Assurance's services as directly tied to their strategic outcomes. 

• Engage executive sponsors early in the sales cycle and maintain those relationships throughout — ensuring Insight Assurance retains visibility and preference at the decision-maker level even during long procurement timelines. 

• Identify and cultivate multi-threaded relationships across the buying committee — mapping champions, influencers, economic buyers, and potential blockers within each target account. 
  
  

Consultative Selling & Solution Positioning 

• Lead enterprise discovery conversations with depth and curiosity — uncovering compliance obligations, audit timelines, multi-framework needs, and organizational risk drivers that create urgency and justify investment in Insight Assurance's services. 

• Position the full breadth of Insight Assurance's service portfolio — SOC 2, ISO 27001, PCI DSS, HITRUST, CMMC, FedRAMP, and penetration testing — as integrated solutions tailored to the enterprise client's specific compliance architecture and business roadmap. 

• Partner with practice leaders, solutions architects, and delivery teams to develop compelling, customized proposals and presentations that clearly articulate value, differentiation, and ROI for enterprise buyers. 

• Lead RFP and RFI responses for enterprise procurement processes — coordinating internal stakeholders, managing timelines, and ensuring Insight Assurance's submissions are technically accurate, commercially competitive, and strategically positioned to win. 

• Stay current on compliance framework developments, regulatory changes, and enterprise cybersecurity trends — using that knowledge to lead informed, credible conversations with sophisticated enterprise buyers. 
  
  

Account Expansion & Retention Partnership 

• Identify and pursue expansion opportunities within existing enterprise accounts — including additional service lines, new business units, subsidiary organizations, and multi-year contract renewals. 

• Partner with the Customer Success team on executive business reviews, renewal conversations, and account health — ensuring seamless handoffs and maintaining the executive relationship throughout the client lifecycle. 

• Develop account growth plans for strategic named accounts — mapping whitespace, multi-year compliance roadmaps, and cross-sell opportunities across Insight Assurance's full service portfolio. 

• Serve as the internal voice of the enterprise customer — providing structured feedback on market requirements, competitive dynamics, and client needs to practice leaders, product, and marketing teams. 
  
  

Cross-Functional Collaboration 

• Partner with Business Development Representatives (BDRs) assigned to your territory — providing strategic account guidance, prioritizing outbound targets, and coaching BDRs on enterprise engagement approaches. 

• Collaborate with Marketing on enterprise-specific go-to-market campaigns, account-based marketing (ABM) initiatives, and enterprise thought leadership content that supports pipeline development in named accounts. 

• Coordinate with practice leaders and delivery teams during the pre-sales process to ensure accurate scoping, realistic timelines, and credible technical positioning in enterprise proposals. 

• Maintain rigorous CRM hygiene (HubSpot or equivalent) — logging all enterprise activity, maintaining accurate opportunity records, and providing timely, reliable forecast updates to sales leadership. 
  
  

Key Performance Indicators 

Annual Recurring Revenue (ARR) Quota: $500k a quarter or $2m Annual 

Pipeline Coverage Ratio: 3x–4x of quarterly quota in qualified pipeline at all times 

Average Deal Size: $10k 

Sales Cycle Management: Disciplined stage progression with ≤30-day average time between stage advances 

Win Rate (Qualified Enterprise Opportunities): ≥25% 

CRM Accuracy: 100% of active opportunities updated weekly; forecast submitted on time 

Hunting: 20% of pipeline self-sourced. 

Required Qualifications 

• 4+ years of B2B sales experience, with a minimum of 3 years in an enterprise or strategic accounts role carrying a quota of $1M+ ARR. 

• Demonstrated track record of closing complex, multi-stakeholder enterprise deals with 6–18 month sales cycles — including MSA and multi-year contract negotiation. 

• Proven ability to build and sustain executive-level relationships (CISO, CTO, CFO, VP-level) across large organizations and navigate complex buying committees. 

• Experience in both hunting and closing roles. 

• Experience selling professional services, cybersecurity, compliance, SaaS, or audit/assurance solutions into enterprise or mid-market accounts strongly preferred. 

• Strong consultative selling skills — you lead with discovery, connect deeply to business outcomes, and build compelling business cases for senior decision-makers. 

• Excellent communication and presentation skills — able to command a boardroom, simplify complex compliance concepts, and tailor messaging to both technical and executive audiences. 

• Highly proficient in CRM platforms (HubSpot, Salesforce, or equivalent) and enterprise sales tools; disciplined approach to pipeline management and forecasting. 

• Self-directed, organized, and accountable — able to manage a complex enterprise territory and multiple concurrent opportunities with minimal oversight. 

• Bachelor's degree in Business, Communications, Marketing, or a related field preferred. 
  
  

Nice to Have 

• Familiarity with cybersecurity compliance frameworks — SOC 2, ISO 27001, PCI DSS, HITRUST, CMMC, or FedRAMP — and the ability to engage credibly with compliance buyers on framework requirements, audit timelines, and certification strategy. 

• Existing executive-level relationships in healthcare, financial services, technology, or defense/government contracting sectors. 

• Experience managing enterprise RFP and RFI processes, including coordination across internal technical, legal, and pricing stakeholders. 

• Familiarity with account-based marketing (ABM) approaches and experience working closely with Marketing on named account campaigns. 

• Prior experience at a Big 4, national audit firm, cybersecurity consultancy, or compliance automation company. 

• Bilingual in English and Spanish — a meaningful advantage given Insight Assurance's Americas-wide client base. 
  
  

Compensation & Benefits 

Structure: Competitive base salary + uncapped performance-based commission. Enterprise AE compensation is structured to reward high-ACV, complex deal execution. 

• Competitive base salary commensurate with enterprise sales experience and market benchmarks. 

• Uncapped commission plan — earn on every dollar of closed revenue with accelerators for above-quota performance. 

• Quarterly performance bonuses tied to pipeline generation and revenue milestones. 

• Flexible Paid Time Off (PTO) and paid holidays. 

• Professional development budget — industry certifications, sales training, and conference participation. 

• 100% remote work environment with a globally distributed, high-performance team. 

• The opportunity to build an enterprise franchise at one of the fastest-growing global audit firms — recognized on the Inc. 5000 and Fast 50 lists. 

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: [email protected] 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