Strategic Enterprise Account Executive

Insight Assurance; Tampa (FL); Remote; USD 120,000 - 210,000; Full time

Benefits offered by this job

Remote work

PTO & holidays

Quarterly performance bonuses

Professional development opportunities

Job summary

Insight Assurance, a global audit firm, seeks an enterprise sales leader to own named accounts and greenfield opportunities across healthcare, financial services, tech, and government sectors. You will drive multi‑month cycles, build C‑suite relationships, and close complex solutions that combine assurance services with compliance automation.

You bring 5+ years in enterprise B2B sales, a track record of $1M+ ARR quotas, and strong executive communication.

Qualifications

• 5+ years of B2B sales experience in enterprise/strategic accounts with big quotas.
• Proven ability to close complex deals with multi-stakeholder buying committees.
• Strong executive-level communication and boardroom presence.
• CRM proficiency and disciplined pipeline management.
• Self-directed and able to run a territory from scratch.
• Bachelor’s degree in business, communications, marketing, or related field preferred.

Responsibilities

• Manage named accounts and greenfield opportunities with 6–18 month cycles.
• Build executive relationships with CISOs, CTOs, CFOs, and VPs.
• Navigate MSAs and multi-year contracts; drive $1M+ ARR quotas.
• Work with cross-functional teams and maintain rigorous CRM hygiene.
• Provide market feedback to practice leaders and sales leadership.

Skills

5+ years B2B sales

Enterprise/strategic accounts

Executive communication

CRM proficiency

Self-directed

Territory ownership

Education

Bachelor's degree in Business, Communications, Marketing, or related field

Job description

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

• 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.

• Demonstratedtrack recordof closing complex, multi-stakeholder enterprise deals with 6–18 monthsales 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 accountsstronglypreferred.

• 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;disciplinedapproach 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

• Competitive base salarycommensuratewith 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.

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