Head of Product, Assurance

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.

We pair that high-velocity culture with a thoughtful hybrid model because we believe flexibility and collaboration both matter. That’s why in the Bay we come together in-office Tuesday through Thursday our high‑impact collaboration days where teams align, strategize, and innovate. Mondays and Fridays are flexible, giving you space for focused work, balance, and autonomy.

If you thrive when you’re empowered, energized, and working with smart, mission-driven people where 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:

Drata is looking for a Head of Product, Assurance to lead product strategy, execution, and team development for significant product lines at Drata – Trust Center & AI Questionnaire Assistance.

This is a high-impact leadership role with end-to-end ownership of product vision, roadmap, customer outcomes, and business performance for a core area of the company. You will partner closely with Engineering, Design, Marketing, Sales, Customer Success, and Finance to ensure the business line continues to expand its market position, deepen customer value, and drive durable growth.

The right leader for this role combines strong product judgment with operational rigor. You can set strategy, make hard tradeoffs, build high-performing teams, and turn customer and market insight into shipped customer outcomes. You know how to balance near-term execution with long-term platform thinking, and you are comfortable owning results in a fast-moving environment.

This is not a narrow feature management role. You will operate like the product leader for a business within the business—responsible for direction, prioritization, organizational effectiveness, and measurable outcomes.

What you’ll do:

Product strategy and business ownership

• Own the vision, strategy, and roadmap for a major product line, ensuring investments align with customer needs, market opportunity, and Drata’s broader company strategy

• Lead portfolio-level prioritization across growth, retention, platform, and innovation work—making deliberate tradeoffs that maximize business impact

• Define the long-term direction of the product line and translate that direction into a clear operating plan for the team and cross-functional partners

• Use customer insight, product data, competitive intelligence, and market trends to identify opportunities for expansion, differentiation, and improved product-market fit

• Act as the primary product leader for the business line, with clear accountability for adoption, retention, expansion, and overall product performance

Customer, market, and commercial leadership

• Be deeply customer-oriented—spend time with customers, prospects, internal stakeholders, and front-line teams to understand the most important problems to solve

• Partner with Sales, Marketing, and Customer Success to ensure product strategy is grounded in market reality and supports successful go-to-market execution

• Help shape positioning, packaging, launch strategy, and commercialization plans for major initiatives within the product line

• Anticipate changes in the market, competitive landscape, and regulatory environment, and adjust strategy with speed and clarity

• Serve as a strong internal and external advocate for the product line and its value to customers

Execution and cross-functional leadership

• Lead the product organization through the full lifecycle of strategy, discovery, roadmap planning, execution, launch, and iteration

• Partner closely with Engineering and Design leaders to deliver high-quality outcomes at a strong pace, without compromising strategic coherence

• Establish clear product goals, metrics, and operating rhythms that create visibility, accountability, and focus across teams

• Drive decision-making in ambiguous situations by bringing structure, clarity, and principled prioritization

• Ensure teams are solving the right problems, learning quickly, and maintaining a high bar for customer value and product quality

Team and organizational leadership

• Build, lead, and develop a strong team of product leaders and product managers, creating an environment of high standards, strong ownership, and continuous growth

• Coach leaders to think strategically, operate effectively, and raise the quality of decision-making across the organization

• Strengthen cross-functional collaboration across Product, Engineering, Design, GTM, and Operations by improving communication, planning, and organizational alignment

• Help shape how the broader product organization scales—its structure, talent density, decision rights, and operating model

• Model Drata’s leadership expectations through transparency, accountability, customer obsession, and a bias toward action

What you’ll bring:

• 10+ years of product management experience building and scaling B2B SaaS products, with meaningful time owning strategy and outcomes for complex product areas

• 5+ years of experience leading and developing high-performing product teams, including managing senior product managers or product leaders

• Proven experience owning a meaningful product business or product line with material revenue responsibility

• Strong track record of defining strategy, translating it into execution, and delivering measurable business results

• Deep customer empathy paired with strong analytical thinking and sound commercial judgment

• Ability to operate at both the strategic and operational levels—comfortable discussing market direction with executives and working through prioritization details with teams

• Strong communication and influence skills, with the ability to align executives and cross-functional leaders around difficult product decisions

• Experience working closely with Engineering, Design, Sales, Marketing, and Customer Success in a high-growth environment

• Demonstrated ability to build clarity and momentum in complex, fast-changing situations

Preferred experience

• Experience leading products in security, compliance, risk, governance, or other trust-critical software categories

• Experience owning both new product investment and scaling an established product line

• Experience in high-growth companies where speed, ambiguity, and organizational change are part of the operating environment

• Strong familiarity with product-led growth, enterprise go-to-market motions, or hybrid SaaS business models

• Experience shaping organizational design, operating cadence, and talent strategy within a product organization

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 their 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: $207,700 - $281,000, subject to change.

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