[Hiring] Strategic Account Executive @Insight Assurance

Role Description

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

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

• 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.