Enterprise And Strategic Account Executive

Summary

Join OffSec, a leading cybersecurity training provider, as an Enterprise & Strategic Account Executive to drive growth in Eastern Europe. You will be responsible for building and expanding relationships with large enterprises and government agencies, closing six-figure deals, and exceeding ARR targets. This role requires a strategic sales professional with experience selling B2B enterprise SaaS, cybersecurity solutions, or technical training products. You will work directly with customers and partners, positioning OffSec as a top provider. The position offers a remote-first culture, competitive salary, performance-based incentives, and career growth opportunities. Join our mission-driven company and help organizations close the cybersecurity skills gap.

Requirements

• 7+ years of experience in enterprise sales selling B2B SaaS, e-learning, or cybersecurity training solutions
• 3+ years of experience selling cybersecurity solutions in Eastern Europe
• Proven track record of exceeding sales targets, particularly in strategic account expansion and high-value enterprise deals
• Strong ability to sell to large enterprises and government agencies, navigating complex procurement processes
• Experience closing six-figure enterprise SaaS, e-learning, or cybersecurity training solutions
• Expertise in solution selling methodologies like MEDDPICC, Challenger, CoM, or Win by Design
• Strong partner & channel sales experience – ability to leverage alliances for accelerated revenue growth
• Proficiency in Salesforce, Gong, and LinkedIn Sales Navigator
• Bachelor’s degree required; MBA is a plus

Responsibilities

• Develop and execute a territory strategy focused on enterprise and strategic accounts in Eastern Europe
• Own the full sales cycle—from prospecting and discovery to closing six-figure deals and expanding key accounts
• Meet and exceed ARR targets while delivering a world-class customer experience
• Engage with C-level executives and security leaders, positioning OffSec as a key partner in cybersecurity workforce development
• Collaborate with partners, channels, and alliances to identify and close new business opportunities
• Lead compelling product demonstrations, sales presentations, and executive briefings for prospects and customers
• Maintain an accurate sales forecast and ensure strong pipeline management
• Act as a trusted advisor to customers, helping them solve critical cybersecurity training and workforce challenges
• Work cross-functionally with marketing, customer success, and product teams to drive customer adoption and satisfaction

Preferred Qualifications

MBA

Benefits

• Remote-first culture
• Competitive salary, performance-based incentives, and career growth opportunities
• Be part of a mission-driven company that helps organizations and governments close the cybersecurity skills gap
• Work hours for this position are flexible and will be performed from a home office