Strategic Enterprise Account Executive

Insight Assurance • Tampa, FL

4d • Remote

About The Position

Insight Assurance is a global audit firm that provides technology-enabled cybersecurity and compliance audit services across frameworks including SOC 2, ISO 27001, PCI DSS, HITRUST, CMMC, and FedRAMP. The company has 170+ professionals and supports nearly 2,000 clients across the Americas, EMEA, and APAC.

This is a strategic, consultative enterprise sales position focused on owning named enterprise accounts and greenfield opportunities across healthcare, financial services, technology, DoD/DIB, and government contracting. The role manages complex sales cycles of 6–18 months, builds C-suite relationships, and develops long-term, multi-service revenue. The position drives opportunities from prospecting through close, supports account expansion and renewals, and collaborates with delivery, practice, marketing, BDR, and customer success teams.

The company describes the role as 100% remote, with a globally distributed, high-performance team. Compensation includes a competitive base salary and quarterly performance bonuses tied to pipeline generation and revenue milestones.

Requirements

• At least 4 years of B2B sales experience, including at least 3 years in an enterprise or strategic accounts role carrying a quota of $1M+ ARR.
• Demonstrated record of closing complex, multi-stakeholder enterprise deals with 6–18-month sales cycles, including MSA and multi-year contract negotiation.
• Ability to build and sustain executive-level relationships with CISO, CTO, CFO, and VP-level stakeholders and navigate complex buying committees.
• Experience in both hunting and closing roles.
• Strong consultative selling skills, including leading discovery, connecting solutions to business outcomes, and building business cases for senior decision-makers.
• Excellent communication and presentation skills, including the ability to present to boardroom-level audiences, explain complex compliance concepts, and tailor messaging to technical and executive audiences.
• High proficiency with CRM platforms such as HubSpot or Salesforce, or equivalent, and enterprise sales tools; disciplined pipeline management and forecasting.
• Self-directed, organized, and accountable, with the ability to manage a complex enterprise territory and multiple concurrent opportunities with minimal oversight.

Nice To Haves

• Experience selling professional services, cybersecurity, compliance, SaaS, or audit/assurance solutions into enterprise or mid-market accounts is strongly preferred.
• Bachelor's degree in Business, Communications, Marketing, or a related field is preferred.

Responsibilities

• Own a named account list and enterprise territory, building and executing account strategies across assigned verticals.
• Drive the full sales cycle from outreach through close, including multi-stakeholder opportunities, MSA and SOW negotiation, and multi-year contract terms.
• Achieve and exceed quarterly and annual revenue quotas while maintaining accurate pipeline forecasts and CRM deal-stage discipline.
• Generate enterprise pipeline through outbound prospecting, executive referrals, partner channels, and industry events.
• Build trusted relationships with CISOs, CTOs, CFOs, and Heads of Compliance, developing engagement across buying committees.
• Develop account intelligence on organizational structure, compliance obligations, and risk priorities, and connect the company's services to client outcomes.
• Maintain executive visibility and preference throughout procurement timelines; identify and manage champions, influencers, and economic buyers.
• Lead discovery conversations to uncover compliance obligations, audit timelines, multi-framework needs, and risk drivers.
• Position the company's service portfolio—including SOC 2, ISO 27001, PCI DSS, HITRUST, CMMC, FedRAMP, and penetration testing—as integrated solutions tailored to enterprise clients.
• Coordinate with practice leaders and delivery teams on customized proposals, presentations, and RFP/RFI responses.
• Stay current on compliance frameworks and regulatory changes and lead informed conversations with enterprise buyers.
• Identify and pursue account expansion opportunities, including additional service lines, business units, subsidiaries, and multi-year renewals.
• Partner with Customer Success on executive business reviews and renewal conversations, maintaining executive relationships throughout the client lifecycle.
• Develop account growth plans covering whitespace, multi-year compliance roadmaps, and cross-sell opportunities.
• Partner with BDRs on territory strategy, outbound prioritization, and enterprise engagement coaching.
• Collaborate with Marketing on ABM campaigns and enterprise thought leadership to drive pipeline in named accounts.
• Maintain CRM hygiene, log enterprise activity, update opportunities weekly, and submit forecasts on time.
• Provide structured market and competitive feedback to practice leaders, Marketing, and sales leadership.

Benefits

• Quarterly performance bonuses tied to pipeline generation and revenue milestones.
• Paid time off (PTO) and paid holidays.
• Professional development budget for industry certifications, sales training, and conference participation.
• 100% remote work environment with a globally distributed team.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed