- Drive automation platform strategy: evaluate, implement, and scale AI questionnaire and trust platforms to dramatically improve response times and automation rates.
- Create GTM enablement programs that drive self-service adoption across sales teams, so AEs and Solutions can confidently field first-pass security questions.
Customer & Revenue Enablement - Develop trust artifacts including security landing pages, whitepapers, industry-specific FAQs, data-flow and architecture overviews, and sales enablement materials.
- Lead live customer security meetings and customer audits with highly regulated customers: banks, financial institutions, and healthcare organizations navigating deep technical and regulatory diligence.
- Build and maintain a security knowledge base and questionnaire-automation workflows so common questions are answered once and reused across the sales org.
Requirements
ABOUT US At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI.
Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook.
Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens.
Before that, Clay led the product and design teams for Google Workspace.
AI, Automation & Scale - Identify broken or manual processes, design scalable solutions, and implement the right tools to maximize efficiency without sacrificing quality.
- Apply automation and AI including AI questionnaire and trust platforms to absorb the volume and depth of regulated-customer diligence, turning days of manual review into minutes.
You'll work day-to-day with: - Sales, GTM and Agent Development integrating Customer Trust workflows into the CRM, streamlining due-diligence processes, and keeping security from becoming a bottleneck in the deal cycle.
experience in compliance, security operations, or customer trust, with 3+ years building or scaling customer-facing security programs from early stage through high growth and seniority and judgment. - Have a proven track record managing enterprise security relationships at scale: you've personally led customer audits and security meetings, built trust with Fortune 500 CISOs, and know how to balance rigor with deal velocity. - Have hands-on
experience supporting global customers and navigating international data protection and AI regimes (e.g., GDPR, UK GDPR, EU AI Act, cross-border transfer and data-residency requirements). - Have strong technical acumen you can explain complex security architectures, compliance frameworks (NIST 800-53, SOC 2, ISO 27001, PCI DSS, HIPAA), and multi-cloud implementations (AWS, GCP) in customer-friendly language. - Have
experience implementing trust automation platforms or building scaled questionnaire-management processes. - Can identify broken processes, design scalable solutions, and implement the right tools to maximize efficiency without sacrificing quality. - Are comfortable presenting to C-level executives and translating technical security concepts for business audiences. - Have a proven track record of cross-functional influence without direct authority — you build partnerships that get things done. - Have
experience partnering with Revenue Operations, Deal Desk, or Sales teams to integrate security into go-to-market motions.
Strong candidates may also: - Have worked in AI/ML or high-growth SaaS companies navigating rapid compliance expansion. - Bring Field CISO or Customer Success Security
experience supporting enterprise deals. - Have familiarity with emerging AI standards (ISO 42001, NIST AI RMF). - Possess relevant certifications (CISA, CRISC, CISM, CISSP, ISO 27001 Lead Auditor). - Have
experience with AI safety or AI agent / model security considerations.
We build trust in AI by making it more accessible, safe, and useful.
BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world.
Experience
This is a role for someone with 10+ years
WHAT YOU'LL BRING You may be a good fit if you: - Have 10+ years of progressive
Benefits
- Build systematic customer intelligence loops that translate the regulatory drivers and recurring concerns across industries and regions healthcare, insurance, financial services, and global markets into prioritized inputs for the Product, Engineering, and Security GRC roadmaps.
experience selling into or supporting highly regulated buyers financial services, banks, healthcare, or insurance and can navigate the depth of their security and regulatory diligence with credibility.
benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision
benefits for you and your family - Life insurance and disability
benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building
benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These
benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans.
Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
Contact
Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/.
Additional details
We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Japan, and Sydney.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family.
These values are the foundation of our work, and we are committed to upholding them in everything we do.
Bret was also one of Google's earliest product managers and co-creator of Google Maps.
We're looking for a seasoned Customer Trust Enablement professional to join the Security Foundations and GRC team.
WHAT YOU'LL DO Program Strategy & Execution (Roadmap Ownership) - Own the Customer Trust roadmap end-to-end, evolving priorities based on company growth, customer needs, and the competitive landscape.
- Define metrics, SLAs, and escalation frameworks for the function, and report on cycle time, coverage, and deal impact to leadership.
- Establish team operating rhythms, metrics reporting, and escalation frameworks.
- Curate Sierra's Trust Center so customers can self-serve answers under NDA.
WHO YOU'LL WORK WITH This role sits in the Security function.