Why You'll Love This RoleAre you a seasoned enterprise sales leader who thrives on flexibility and delivering results?
Want to sell a proven, high-impact offering trusted by top-tier global brands?At the Cyber Leadership Institute (CLI), we empowering cybersecurity leaders to thrive since 2018 with our acclaimed B2C cyber leadership programs—and now, we're looking for a fractional head of sales to drive adoption of our B2B offering, Enterprise Premium Membership to support cybersecurity, technology and risk teams in organizations.In this role, you'll work directly with a co-founder and be supported by a sales and marketing operations team, to identify, engage, and close enterprise clients.
You won't just be selling access to a pioneering digital learning and career development platform—you'll be enabling companies to strengthen their cybersecurity leadership skills bench through a proven suite of executive programs trusted by industry-leading brands.Who We AreThe Cyber Leadership Institute is a trusted partner to organizations in over 70 countries, providing a unique platform that blends on-demand cyber leadership programs, strategic tools, and a powerful peer community.Our Enterprise Premium Membership gives companies scalable access to our entire platform—helping them upskill cybersecurity, technology, risk teams etc, and embed cyber resilience culture across the business.
Now, we're scaling rapidly and need a commercially minded partner to help us grow.What You'll Be DoingSell Enterprise Premium Memberships: Own the got to market strategy for our latest flagship offering, targeting CISOs, CIOs, HRDs, and other senior stakeholders in large enterprises.Build Strategic Pipelines: Identify ideal clients, qualify leads, and monitor sales funnels metrics that drive long-term recurring revenue.Lead Outreach and Follow-Through: Conduct outreach, deliver tailored pitches and demos, and manage the full sales cycle through to signed agreements.Refine and Scale the Sales Model: Work closely with a co-founder and sales/marketing operations team to evolve our sales playbook, messaging, and go-to-market strategies.Collaborate Across Teams: Align with marketing and operations to ensure messaging consistency, pipeline health, and seamless onboarding of new enterprise members.What We're Looking ForB2B Enterprise Sales Experience: Minimum 5 years selling to mid-to-large enterprises, ideally within learning platforms, or cybersecurity services.Fractional Sales Leadership: Part-time employment, ideally two and half days a week, who will be a results-driven operator looking to make an outsized impact in a flexible roleC-Level Confidence: You can speak the language of CISOs, CIOs, and Senior People Leaders, and know how to communicate the ROI of leadership development and digital platform adoption.Commercial Acumen: You have a track record of closing multi-stakeholder enterprise deals and enjoy the challenge of B2B consultative sales.Proactive and Collaborative: You operate independently, but love being part of a mission-driven team with big growth ambitions.Why CLI is DifferentFounder-Led Sales Advantage: You'll work alongside CLI's founders, who already have deep, trusted relationships with CISOs, CIOs, CROs, etc.
across the globe—giving you a warm-entry advantage into enterprise deals.World-Class Product: Our platform and programs are trusted by cybersecurity leaders at some of the world's most iconic brands—making your sales conversations credible from the first pitch.Mission With Impact: Every sale you close helps accelerate the careers of cyber leaders and directly strengthens global cyber resilience.High-Leverage, Flexible Role: Enjoy the freedom of fractional work with the earning potential and impact of a core team member.Ready to help take a world-class cyber leadership platform global?Apply now and let's build the next chapter—together.
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