Paid Expert Interview – CRO, CISO, GRC, Sales Engineer or SaaS Founder
Job Description
Company: Upwork
Description:
I’m conducting market research around enterprise vendor security reviews, customer security questionnaires, vendor assessments, customer trust workflows, and enterprise sales friction.
This is NOT a sales call.
I’m looking to speak with people who have direct experience with one or more of the following:
• Founder / CEO of a B2B SaaS company
• CRO / VP Sales / Revenue leader
• Sales Engineer / Solutions Engineer
• Customer Trust / Security Assurance
• GRC / Compliance
• CISO / vCISO
• Vendor Risk / Buyer-side Assessment Team
• Security Auditor
• Fractional advisor in any of the above areas
I’m specifically looking for perspectives from:
• Buyer side
• Seller side
• Practitioners operating inside the process
• Advisors who have seen multiple companies go through these reviews
The goal is to better understand:
• Where enterprise security reviews create friction
• Whether sellers usually know why reviews stall
• How much feedback buyers provide
• What buyers wish sellers understood better
• What sellers misunderstand about enterprise security reviews
• Whether trust, credibility, responsiveness, and perceived maturity influence outcomes
• Whether security-review-related sales friction is significant enough to justify outside help
Compensation:
• $50 for a 30-minute discussion
• Additional paid follow-up discussion may be offered if the conversation is particularly relevant
Preference will be given to people with recent experience selling to, assessing, supporting, or reviewing North American enterprise customers.
To apply, please answer:
1. What has your direct experience been with enterprise security reviews, vendor assessments, customer security questionnaires, customer trust workflows, or vendor risk reviews?
2. Which perspective best describes your experience?
• Buyer side
• Seller side
• Both
• Advisory / Consulting
3. What role(s) were you in when dealing with these processes?
4. How recent is your experience?
• Currently involved
• Within the last 12 months
• Within the last 3 years
• More than 3 years ago
5. Approximately how many vendor assessments / enterprise security reviews have you participated in during the last 12 months?
6. What types of companies and verticals have you seen this with?
(SaaS, healthcare, fintech, cybersecurity, AI/data, regulated industries, enterprise, mid-market, etc.)
7. What experience do you have with North American enterprise customers or North American enterprise security review processes?
8. Briefly describe one situation where a security review, assessment, or questionnaire process affected a deal, sales cycle, internal workload, customer relationship, or buying decision.
Please do not disclose confidential, proprietary, or customer-specific information.
I’m specifically looking for thoughtful practitioners with firsthand experience and strong opinions based on real-world exposure.
Source: Upwork
