Strategic Enterprise Account Executive

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  

This is a strategic, consultative enterprise sales role — not a transactional one. You'll own a portfolio of named enterprise accounts and greenfield opportunities across key verticals (healthcare, financial services, technology, DoD/DIB, government contracting), running complex 6–18-month sales cycles and building C-suite relationships that generate long-term, multi-service revenue. You know the compliance landscape, command a boardroom, and close enterprise deals that others can't.

Requirements

Key Responsibilities

Pipeline & Revenue

• The Enterprise Track Record: You must have spent 5+ years managing strategic/enterprise accounts and carrying a $1M+ ARR quota.
• Complex Deal Execution: You need to prove you can survive and win 6–18-month sales cycles, navigate multi-stakeholder corporate mazes, and handle the legal/procurement grind (MSAs, multi-year commitments).
• Executive Presence: You must be able to pitch directly to the C-suite and VPs, translating complex compliance solutions into business value.
• High Autonomy: You are running your territory like a business owner and are able to do it from scratch.

Executive Relationships

• Build trusted advisor relationships with CISOs, CTOs, CFOs, and Heads of Compliance — developing multi-threaded engagement across the buying committee.
• Develop deep account intelligence on organizational structure, compliance obligations, and risk priorities — connecting Insight Assurance's services to each client's strategic outcomes.
• Maintain executive visibility and preference throughout long procurement timelines; map and manage champions, influencers, and economic buyers within every target account.

Consultative Selling & Positioning

• The Domain Expertise: Background in SOC 2, ISO 27001, or FedRAMP. If you already know how to talk to compliance buyers and understand security frameworks, you save them months of training.
• Industry Network: An existing rolodex of executive contacts in high-security, high-regulation sectors like Healthcare, Finance, Tech, or Defense.
• The Pedigree: Coming from a Big 4 firm, a cybersecurity consultancy, or a compliance automation company makes you a plug-and-play hire.
• The Multiplier: Bilingual English/Spanish skills to unlock their expanding Latin American/Americas territory.

Account Expansion & Retention

• Identify and pursue expansion opportunities within named accounts — additional service lines, new business units, subsidiary orgs, and multi-year renewals.
• Develop account growth plans mapping whitespace, multi-year compliance roadmaps, and cross-sell opportunities across the IA portfolio.

Cross-Functional Collaboration

• Partner with BDRs on territory strategy, outbound prioritization, and enterprise engagement coaching.
• Maintain rigorous CRM hygiene — all enterprise activity logged, opportunities updated weekly, forecasts submitted on time.
• Provide structured market and competitive feedback to practice leaders, marketing, and sales leadership.

Key Performance Indicators

Annual Recurring Revenue (ARR) Quota: $500K per quarter / $2M annually

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: Minimum 20% of pipeline self-sourced

Required Qualifications  

• 5+ 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

Benefits

• Competitive base salary commensurate with enterprise sales experience and market benchmarks. 
• Quarterly performance bonuses tied to pipeline generation and revenue milestones. 

• 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: View email address on aiapply.co 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