Role OverviewThis 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 ResponsibilitiesPipeline & 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 IndicatorsAnnual 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.
