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.
Key Responsibilities
Pipeline & Revenue
- Own a named account list and enterprise territory — build and execute an account strategy that penetrates high-value targets across assigned verticals.
- Drive the full sales cycle from outreach through close — managing multi-stakeholder opportunities, MSA and SOW negotiation, and multi-year contract terms.
- Consistently achieve and exceed quarterly and annual revenue quotas; maintain accurate pipeline forecasting and deal-stage discipline in CRM.
- Generate enterprise pipeline through outbound prospecting, executive referrals, partner channels, and industry events.
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
- Lead discovery conversations that uncover compliance obligations, audit timelines, multi-framework needs, and risk drivers that create urgency and justify investment.
- Position the full IA service portfolio — SOC 2, ISO 27001, PCI DSS, HITRUST, CMMC, FedRAMP, penetration testing — as integrated solutions tailored to each enterprise client's compliance architecture.
- Coordinate with practice leaders and delivery teams to develop customized proposals, presentations, and RFP/RFI responses that are technically accurate and commercially competitive.
- Stay current on compliance framework developments and regulatory changes; lead credible, informed conversations with sophisticated enterprise buyers.
Account Expansion & Retention
- Identify and pursue expansion opportunities within named accounts — additional service lines, new business units, subsidiary orgs, and multi-year renewals.
- Partner with Customer Success on executive business reviews and renewal conversations; maintain the executive relationship throughout the client lifecycle.
- 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.
- Collaborate with Marketing on ABM campaigns and enterprise thought leadership that drives pipeline in named accounts.
- 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
- 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: 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
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