Cybersecurity & Compliance Delivery Specialist (Gov Frameworks | Contract-to-Hire | Remote)Why This Role is Different
This is not a generic compliance role.
At eSilo, we work with regulated businesses that need to meet frameworks like CMMC, NIST 800-171, and HIPAA while still operating efficiently. Our clients are not textbook environments. They have constraints, legacy systems, competing priorities, and real business pressures.
This role requires much more than following a checklist.
You will be expected to interpret requirements, apply judgment, and make practical recommendations based on incomplete information. There is rarely a single “correct” answer. Instead, there are multiple viable approaches with tradeoffs, and you must be comfortable selecting a path and explaining why it makes sense for that specific client.
If you prefer rigid instructions, lots of structure, step-by-step playbooks, or environments where every decision is clearly laid out and predefined, this role will not be a good fit.
Success here requires:
- Solution orientation
- Comfort operating in ambiguity
- Strong critical thinking and problem-solving
- A risk-based mindset, not a checkbox mentality
- Willingness to balance “ideal” vs “practical” solutions
- Confidence in making and defending recommendations
You will design & implement solutions based on industry frameworks and best practices -- but your value comes from how you apply those principles to real-world environments.
If you take pride in producing clean, accurate work, can think beyond the frameworks, and want to grow into higher-impact advisory roles over time, this is a strong fit.
Position Overview
- Job Type: Contract-to-Hire (within 6 months or less), Full-Time upon conversion
- Location: Remote
- Hours: 20–40 hours/week during contract phase. The specifics can be negotiated.
- Reporting: CEO / Senior Advisor
Role Summary
The Cybersecurity & Compliance Delivery Specialist is a hands-on execution role responsible for delivering compliance and security engagements for regulated clients.
You will focus on assessments, remediation, policy development, and audit readiness. This role is execution-first and operates within a structured delivery model designed for efficiency and quality.
Client Interaction Model
You are the primary day-to-day owner of the client engagement.
You will lead working sessions, drive to agreed upon timelines, and serve as the main point of contact across most interactions, including routine executive updates to clients.
Your responsibilities include:
- Leading working sessions and status updates
- Identifying emerging risks and opportunities to improve processes
- Gathering information and validating control implementation
- Requesting, reviewing, and critiquing evidence
- Translating requirements into an actionable roadmap and clear next steps
- Driving follow-ups and maintaining momentum
You will primarily work with the clients’ IT managers, process owners, and compliance staff, with occasional interaction with C-suite client stakeholders such as CFO, COO, or CIO for straightforward updates.
An eSilo Senior Advisor (Fractional CIO/CISO) and/or Subject Matter Expert (SME) will be engaged on your projects part-time to provide:
- Strategic direction and prioritization
- Input on complex or high-risk decisions
- Expertise on the subject industry, framework, or technology
- Support for sensitive executive discussions
- Act as a “thought partner” for you on the engagement
In practice:
- You own day-to-day execution and client communication
- You form initial recommendations and align with the Senior Advisor as needed
- You escalate only when tradeoffs are material or unclear
This role requires comfort operating independently, even in areas that are new to you, while using senior leadership as a strategic partner.
Responsibilities
- Perform gap assessments against CMMC, NIST 800-171, HIPAA, and other frameworks
- Identify ‘hidden’ risks in current practices and explain the impact in business terms
- Translate requirements into practical, implementable controls that fit business context
- Develop remediation plans with clear prioritization
- Draft and refine security policies and procedures
- Identify, collect, and validate audit evidence
- Support clients through audit readiness
- Manage assigned tasks across multiple client engagements
- Track deliverables, timelines, and dependencies
- Escalate risks and blockers early
- Contribute to improving templates, processes, and delivery efficiency
Contract-to-Hire Conversion Milestones (within 6 months)
You will be evaluated on the following “Top 10 List” to determine readiness for conversion:
- Complete at least 2 client assessments.
- Demonstrate identification of risks that fall outside of standard frameworks
- Deliver clear findings, control mapping, and remediation plans
- Demonstrate ability to defend your recommendations in business terms, i.e. why doing this is good for the business, not just because it’s required in the framework.
- Demonstrate effective communication across 3 modalities: written word, visual presentation, and verbal delivery
- Draft 3–6 policies aligned to frameworks
- Drive your projects independently to deliver on time and under budget
- Deliver high quality work with minimal rework
- Manage multiple high pressure workstreams effectively
- Demonstrated use of AI to accelerate workflows without impacting privacy or security
What Success Looks Like
- Produces accurate, complete work with minimal revision
- Operates reliably within structured processes
- Demonstrates working knowledge of a range of compliance frameworks
- Provides practical, environment-aware recommendations
- Communicates clearly and follows through consistently
QualificationsRequired
- 3–7+ years in cybersecurity, compliance, or IT audit
- Hands-on experience with CMMC, NIST 800-171, HIPAA, or similar
- Experience supporting government contractors or regulated organizations
- Strong documentation and execution skills
Preferred
- Background in SaaS or technical environments
- Demonstrated interest in automation or AI-assisted workflows
- Experience with AWS or Azure environments
- Exposure to FedRAMP
CompensationContract Phase
- $60–$85/hour
- 20–40 hours/week
Full-Time Conversion
- $95K – $110K base
- 5–10% performance bonus (utilization and delivery quality)
- Opportunity to earn additional compensation on new clients introduced to eSilo
Growth Path
This role can evolve into:
- Fractional CISO / advisory roles
- Subject Matter Expert (SME) roles
- Government compliance specialist (CMMC/FedRAMP)
- AI and automation-driven delivery roles
Who This Role Fits Best
- You prefer execution over strategy (for now)
- You like to plan and execute work independently, with escalation support where needed
- You are comfortable with ambiguity and enjoy exercising judgment in your work
- You take ownership of deadlines and quality
- You want exposure to higher-level advisory work over time
Who This Role Is Not For
- Candidates looking for a pure advisory role without hands-on detailed work
- Candidates looking for a traditional compliance or GRC role
- Candidates who prefer formal checklists or who dislike uncertainty or unstructured work
- Candidates who dislike forward-facing client work (presentations, meeting facilitator, etc)
About eSilo
We are a cybersecurity and compliance advisory firm focused on regulated industries. Our clients rely on us to deliver practical, high-quality solutions that stand up to audit and support real business operations.
We are building a scalable consulting model and looking for people who want to grow with it.
Pay: $60.00 - $85.00 per hour
Work Location: Remote