United States & Canada (Remote) — $500 per qualified meeting

this post was created on behalf of one of Glencoco’s clients.

Our client is a fast-growing B2B software company in the AI governance and security space. They provide a self-hosted, compliance-ready control plane that gives IT and security leaders centralized visibility, permissioning, audit logs, and policy enforcement over how employees use AI tools (e.g., ChatGPT, Copilot, Gemini) across the business—without disrupting end-user workflows.

They’re leaning into a massive, fast-emerging need: shadow AI. Mid-market organizations are adopting AI tools quickly, but leadership lacks a single source of truth or enforcement layer. Compliance pressure (SOC 2, HIPAA, ISO, board reviews) and data exposure concerns are turning this into a budgeted priority.

This is a fractional SDR role focused on generating top-of-funnel and booking short, “coffee-break style” discovery calls (14–15 minutes) with senior IT/security leaders.

Compensation: $500 commission per qualified meeting.

What you’ll do:

• Run targeted outbound to senior technical buyers via phone, email, and LinkedIn
• Qualify accounts against clear criteria (company size, persona, industry, and pain)
• Uncover and articulate pains around shadow AI, compliance pressure, and data exposure
• Book concise 14–15 minute discovery calls and manage handoffs to the closing team
• Personalize outreach using provided messaging, scripts, and objection loops
• Track activity, pipeline, and results in the client’s CRM/tools

What you’ll need to succeed:

• 3–5+ years of high-velocity B2B outbound experience; proven cold-calling chops
• Comfortable booking meetings with CISOs, CIOs, and VP/Director-level IT & Security leaders
• Familiarity with security/IT concepts (e.g., audit logs, permissioning, SSO/IdP, SIEM, DLP)
• Strong discovery skills; able to surface pain without over-selling
• Clarity, brevity, and confidence on the phone; non-supplicative tone with senior buyers
• Bonus: experience in AI tooling, data governance, or security SaaS

Who you’ll be calling:

• Titles: CISO, CIO, VP/Head of Security, Director of Information Security, VP/Head/Director of IT/Infrastructure/Enterprise Apps, IT Manager (at sub-500-employee companies)
• Company size: 200–2,000 employees
• Geography: U.S. and Canada
• Industries: Any non-software verticals (finance, healthcare, insurance, manufacturing, logistics, legal, professional services, retail, energy, education, government contractors, nonprofits)

What counts as a qualified meeting (and pays $500):

• Company size: U.S. or Canada; 200–2,000 employees
• Persona: CISO, VP/Head of Security, Director of InfoSec, CIO, VP/Head/Director of IT/Technology/Infrastructure/Enterprise Apps, IT Manager (only if company <500 employees), or equivalent decision-maker/influencer for IT/security/AI tooling
• Industry: Excludes software/SaaS vendors, IT services firms, and cybersecurity vendors
• Pain: Prospect acknowledges at least one of the following:
  • Shadow AI visibility gap (employees using AI tools without centralized visibility)
  • Data exposure or IP leakage concern (sensitive data potentially entering AI tools)
  • Compliance/policy/enforcement gap (e.g., SOC 2, HIPAA, ISO, board or auditor pressure where a paper policy isn’t enough)
  • AI tool request overload (teams asking for new AI tools without a clear approval framework)

Why reps like this campaign:

• Massive, timely problem with senior visibility and clear ROI drivers
• Short, low-commitment intro calls that resonate with technical buyers
• Strong talk track and objection-handling playbooks provided
• Opportunity to become a go-to expert in a fast-growing category

Logistics:

• Engagement: Fractional/1099 contractor; remote; flexible hours
• Pay: $500 per qualified meeting (per criteria above)
• Ramp: Training, ICP, call frameworks, and objection loops provided
• Tools: You’ll work within the client’s enablement stack and CRM

How to apply:

• Send a brief note highlighting relevant outbound experience (especially booking CISOs/CIOs), a recent cold-calling win, and your availability. Include a resume or LinkedIn profile link.

What you’ll do:

• Grow top of sales funnel through cold outbound campaigns
• Call into mobile-enriched leads who fit the target persona
• Pitch and qualify those leads
• Generate sales-ready meetings and opportunities for Account Executives using qualification criteria
• Utilize your active listening skills to understand and uncover customer needs and business problems to effectively communicate how the Client can solve them
• Develop strong sales and product knowledge

You’ll receive access to:

• An deep pool of highly targeted, mobile enriched leads
• Best-of-breed power dialer technology, which leverages smart algorithms to optimize the number of conversations you can have each hour
• Easy to use, personal CRM for tracking the accounts you work
• AI-assisted email tools

You should check out this role if:

• You’re excited to work as a freelance SDR, and have the autonomy to work flexible hours
• You’re based in the US and desire to work remotely
• You have a laptop or desktop computer and stable internet connection