Field CISO

Cacheflow; United States; On-site; USD 210,000 - 350,000; Full time

Benefits offered by this job

Stock equity

Health & Wellness

Financial well-being

Family support

Growth & development

Time off & flexibility

Job summary

Drata seeks a Field Chief Information Security Officer to lead security and GRC in a senior, remote, U.S.-based role. You will be the credible security voice in customer conversations, industry events, and strategic initiatives across Americas and EMEA.

This role requires 15+ years in security/GRC, 10+ years leading teams, and 5+ years in a CISO capacity, with deep SaaS/cloud-native risk and regulatory expertise. Expect cross-functional collaboration and regular travel.

Qualifications

• 15+ years in security and GRC with leadership experience.
• Strong understanding of ISO27001, SOC 2, HIPAA, GDPR and NIST CSF.
• Excellent communication across boardroom and technical teams.
• Willingness to travel 50–75% and represent Drata publicly.

Responsibilities

• Partner with Sales, CS and Marketing on strategic enterprise opportunities.
• Lead executive briefings and CISO-to-CISO discussions to build trust.
• Represent Drata at industry conferences and regional roundtables.
• Share field insights via webinars, bylines and press opportunities.
• Advise leadership on regulatory shifts and security strategy direction.
• Shape product roadmap and GTM strategies based on field feedback.
• Provide strategic guidance to resolve high-stakes security questions.

Skills

Security leadership

Executive communication

Customer-facing collaboration

Strategic thinking

Education

CISSP / CISM / CRISC / CCSP (certs a plus)

Tools

Drata platform knowledge

Job description

Our Mission & Values:

At Drata, we help companies earn and keep the trust of their users, customers, partners, and prospects. We’re the proof layer that shows great companies deserve the trust they aim to build.

We live our values every day. Built on Trust means consistency is everything. Act with Integrity by always doing the right thing. Being Customer-Obsessed keeps the people we serve at the center of our work. Competitive Fire drives us to push ourselves harder than anyone else. Diversity brings unique perspectives that lead to better solutions. Automation First ensures we save time and money by making efficiency a priority.

Our Culture & Work Style

At Drata, we’re not just building software - we’re building a mindset. Everything we do springs from:

• Be a Driver (Owner‑Operator Mentality): Own your work. Improve relentlessly. Deliver results.

• Move at Drata Speed (Precision & Velocity): Fast decisions. Quick learning. Immediate impact.

• Stay Mission-Driven (Customer‑Obsessed): Challenge assumptions. Deliver value. Stay hungry.

If you thrive when you’re empowered, energized, and working with smart, mission-driven people, you’ll feel at home here.

Why Join The Drata Team?

The best way to understand the Driver’s Mindset is to see it in action. We’re an award-winning, mission-driven team of 600+ people worldwide, united by a culture that values trust, speed, and continuous growth.

• See the Speed: Watch our CEO, Adam Markowitz, discuss the hyper-growth journey, from $0 to $100M ARR in just four years

• Hear the Voice of the Team: Explore our "Life at Drata" page for employee testimonials on our collaborative and the growth opportunities available.

• Experience the Impact: See why we are consistently recognized on Fortune's Best Workplaces lists.

• Connect with Us on Socials: LinkedIn - follow us for company updates, employee stories, and career news.

Job Summary:

As Drata scales, we want our security and GRC leadership to be able to meet our customers’ needs in more places at once—in strategic customer conversations, on stage at industry events, and in the broader conversations happening across our security and GRC communities. We’re looking for a Field Chief Information Security Officer to join Drata’s Security & GRC organization, reporting directly to our SVP, Security & CISO, to help carry our vision to a wider audience. Your primary mission: be Drata's credible, practitioner-level security and GRC voice in the field.

This role is a senior, remote, U.S.-based security and GRC leadership role, ideally based on the East Coast to cover both the Americas and EMEA regions. As one of the most senior individual contributor roles in Drata's Security & Trust organization, this role shapes how Drata responds to the industry, informs the product experience, and aids in the strategic positioning of Drata’s future to acutely meet industry needs. This position is built for someone who has led security and GRC programs before and is excited to bring that experience directly to our customers, prospects, and industry peers. You’ll work closely with our go-to-market, customer success, and marketing teams, but your foundations are still rooted in technical security and GRC leadership—that is what will make you credible in the room among peers and is critical to the success of this role. Given the nature of our platform, this person will spend as much time in GRC conversations as in traditional security conversations due the complementary nature and inseparability of these functions.

What you’ll do:

• Partner with our amazing Sales, Customer Success, and Marketing teams on our most strategic enterprise and F500/G2000 opportunities—bringing tried‑and‑true security and GRC expertise into the conversation when customers need it most.

• Lead executive briefings and CISO-to-CISO conversations that build trust and help prospective customers feel confident in their decision.

• Represent Drata at industry conferences, CISO dinners, and regional roundtables across the Americas, EMEA, and APAC regions, building genuine relationships across the security and GRC community.

• Share what you’re hearing in the field through webinars, panels, bylines, and press opportunities that build Drata’s voice and credibility in the security and GRC market.

• Advise our CISO, CMO, CRO, and executive leadership team members directly on emerging regulatory shifts, systemic industry risk, and where Drata's security and GRC strategy needs to head next.

• Provide strategy and direction to company-wide responses to major shifts in our industry, such as new regulatory regimes, major certifications, systemic risk events surfaced by our customers, reaffirming the direction set has a lasting effect on Drata's market position.

• Raise the overall security and GRC bar across Drata and industry-wide through knowledge sharing, internal and external forums, and pattern-setting.

• Equip our sales teams with the security and GRC context and talking points they need to navigate technical conversations with confidence.

• Draw on your own relationships and reputation in the security and GRC community to open doors and build trust for Drata.

• Partner with Marketing and GTM leadership to help plan executive events, speaking engagements, dinners, and roundtables throughout the year.

• Act as a real, ongoing influence on our product roadmap and go-to-market growth strategy — not just relaying field feedback, but helping shape the decisions themselves based on hands on experience corroborated with customer needs.

• Step in on the highest-stakes, least-defined security and GRC questions facing the business—the ones without an existing playbook—and provide the strategic direction to resolve them.

• Approach every external conversation as an extension of Drata’s security and GRC program, with the same care and integrity you’d bring internally.

• Work alongside our own internal security and GRC team members to support any critical company initiatives as deemed necessary.

What you’ll bring:

• 15+ years of progressive experience in security and GRC, including 10+ years leading and managing teams and 5+ years in the CISO seat (as a CISO, Deputy CISO, or equivalent senior security and GRC leader).

• A strong grasp of the compliance frameworks our customers care about — including ISO 27001, SOC 2, HIPAA, FedRAMP, GDPR, NIST CSF, PCI DSS, and CCPA — and the practical experience to speak to them with real depth.

• Excellent communication skills, with the ability to move comfortably between boardroom conversations and technical deep-dives.

• A genuine reputation and network within the security and GRC community, built through your own experience leading programs and engaging with peers.

• A track record of operating at the most senior individual contributor level of a security or GRC organization, where leadership and peers already come to you for strategic direction, not just execution.

• Comfort working with ambiguity — turning undefined, fast-moving problems like regulatory direction, market shifts, or systemic risk into clear strategy, not just talking points.

• Experience partnering with go-to-market teams in customer-facing conversations, and comfort with the pace and cadence of enterprise sales cycles.

• A track record of thought leadership—speaking, writing, or other public and social engagement that reflects your experience and perspective.

• Familiarity with SaaS and cloud-native environments, along with a thoughtful perspective on how AI is shaping both security and GRC risk and practice.

• Familiarity with compliance automation platforms like Drata, so you can speak to our own product with the same credibility you bring to security and GRC itself.

• Openness to travel regularly and represent Drata’s security and GRC program in a public-facing capacity.

• A curious, thoughtful approach to using AI in your own work, with the judgment to apply it responsibly.

Requirements:

• 15+ years in security and GRC, including 10+ years leading and managing security and GRC teams and 5+ years in the CISO seat (as a CISO, Deputy CISO, or equivalent senior security and GRC leader).

• Ideally either based on the East Coast of the U.S. or willing to work EST hours to support coverage across the Americas and EMEA time zones.

• Willingness to travel regularly - 50-75% (including international travel) for customer meetings, conferences, and field events.

• Professional certifications such as CISSP, CISM, CRISC, or CCSP are a plus (though real, tenured experience carries more weight).

How we support you:

At Drata, our people are our strongest advantage—and we prove it with support that exceeds industry standards. Our total rewards package is designed to power your well-being, accelerate your growth, and keep your work-life balance thriving.

Explore how we invest in your Life at Drata.

• Shared Success: We provide stock equity to ensure that as the company grows, you share directly in that success. Equity gives every employee a sense of ownership and the opportunity to celebrate our wins together—because your contributions don’t just support our progress; they help drive our collective success.

• Health & Wellness: Up to 100% employer-paid premiums for medical, dental, and vision coverage for employees and dependents, along with comprehensive wellness benefits and healthcare concierge services designed to support your needs beyond traditional insurance.

• Financial Well-being: A comprehensive suite of financial benefits, including a 401(k) plan, company-paid life and disability insurance, tax-advantaged spending accounts, and a range of discounted voluntary offerings to help you customize and strengthen your overall financial position.

• Family Support: We want to support you in life's most important moments, so we offer a paid Parental Leave policy, after six months of employment. Employees also receive access to Kindbody fertility and family-building benefits and dedicated leave specialists who help guide you through the entire process.

• Growth & Development: Generous annual stipends for both professional and personal development, empowering you to invest in your continued growth. You’ll also have access to a wide range of internal learning opportunities, ensuring you can build new skills, deepen your expertise, and advance your career with confidence.

• Time Off & Flexibility: We believe that to do your best work, you should get the time you need for rest, rejuvenation and recovery. Drata offers a flexible vacation policy, paid holidays, and other perks to recharge.

This role will receive a competitive base salary, benefits, and stock, typically in the form of Restricted Stock Units (RSUs). The applicable salary range for this role is: $210,000 - $350,000.

A variety of factors are considered when determining someone’s leveling and compensation–including a candidate’s professional background and experience. These ranges may be modified in the future and final offer amounts may vary from the amounts listed above.