Jobs in Pebble Creek Florida Remote

Redress Compliance is an independent software licensing and cloud advisory firm. We help global enterprises reduce costs, mitigate compliance risks, and negotiate better outcomes with vendors including Oracle, Microsoft, IBM, SAP, Salesforce, ServiceNow, and Workday. We are Gartner recommended, vendor independent, and have delivered 500+ client engagements across North America, EMEA, APAC, and Latin America. We are scaling our delivery team and building out the analytical backbone that supports every client engagement.

Role Description

This is a hands on licensing analysis role. You will be responsible for conducting software baselines, effective licence positions (ELPs), compliance assessments, and deployment analyses across multiple vendor estates. Your core vendors will be Microsoft, VMware (Broadcom), Autodesk, and Adobe. Experience with Oracle, IBM, SAP, or ServiceNow is a strong plus and will expand the engagements you work on.

You will work alongside our senior consultants and founders, providing the detailed data work and analysis that underpins our advisory, negotiation, and audit defence engagements. This is not a strategy or sales role. It is the analytical engine room where accuracy, thoroughness, and speed directly drive client outcomes.

Day to day, you will:

• Build and maintain software baselines and ELPs across Microsoft, VMware, Autodesk, and Adobe estates
• Collect, normalise, and reconcile deployment data from client environments (SCCM, MECM, vCenter, Adobe Admin Console, Autodesk Account, and similar tools)
• Map deployed software against entitlements, contracts, and licence agreements to identify compliance gaps and optimisation opportunities
• Produce client ready reports that clearly present licensing positions, risks, and recommendations
• Support audit defence engagements by preparing detailed compliance documentation and counter positions
• Assist with Vendor Shield subscriber quarterly reviews by maintaining up to date licensing positions across covered vendors
• Track vendor programme changes, metric updates, and licensing model shifts for your covered vendors
• Collaborate with senior consultants on multi vendor engagements, contributing analysis across the full vendor estate

Qualifications

• 3+ years of experience in software licensing analysis, software asset management (SAM), or licence compliance
• Demonstrated ability to build ELPs and software baselines for at least two of the following: Microsoft, VMware/Broadcom, Autodesk, Adobe
• Hands on experience with deployment discovery tools (SCCM/MECM, vCenter, Snow, Flexera, ServiceNow SAM, or similar)
• Strong Excel and data manipulation skills. You will be working with large datasets daily
• Understanding of common licensing models (per user, per device, per core, subscription, named user, concurrent)
• Detail oriented and methodical. Errors in baselines create real compliance risk for clients
• Comfortable working remotely and managing multiple concurrent deliverables with clear deadlines
• Good written communication. You will need to explain technical findings in plain language for client audiences
• Experience with Oracle, IBM, SAP, or ServiceNow licensing is a valuable plus
• SAM related certifications (CSAM, ITIL, or vendor specific) are welcome but not required

What makes this role different

At most SAM practices you run the same tool report on repeat. Here you are working on live advisory and negotiation engagements where your analysis directly shapes multi million dollar licensing decisions. You will see the commercial impact of your work, not just file reports into a queue. You are joining a small, high calibre team with direct access to the founders and senior consultants, and you will build deep expertise across multiple vendors rather than being siloed into one.

Redress Compliance is an independent software licensing and cloud advisory firm. We help global enterprises reduce costs, mitigate compliance risks, and negotiate better outcomes with vendors including Oracle, Microsoft, IBM, SAP, Salesforce, ServiceNow, and Workday. We are Gartner recommended, vendor independent, and have delivered 500+ client engagements across North America, EMEA, APAC, and Latin America. We are scaling fast and building out our in house delivery capability across all major vendors.

Role Description

This is our first in house Microsoft specialist hire. You will lead client engagements across the full Microsoft licensing estate, including Enterprise Agreements, Microsoft 365, Azure, Copilot, and Server/CAL. You will work directly with the founders to deliver advisory, negotiation support, and compliance analysis for enterprise clients with Microsoft spend ranging from $2M to $50M+.

Today we subcontract Microsoft work at an 80/20 split. This hire brings delivery in house and is one of the highest impact moves on our margin roadmap. You will own the Microsoft practice and help us build it into a core revenue line alongside Oracle.

Day to day, you will:

• Lead Microsoft EA and SCE renewal negotiations on behalf of enterprise clients
• Conduct licensing position assessments across Microsoft 365, Azure, Dynamics, and Server/CAL environments
• Advise clients on cost optimisation strategies including licence harvesting, subscription right sizing, and Azure commitment planning
• Deliver compliance risk assessments and audit defence support for Microsoft engagements
• Support Vendor Shield subscription clients with ongoing Microsoft advisory as part of their quarterly reviews
• Brief clients on Microsoft programme changes, pricing shifts, and licensing policy updates
• Collaborate with the founders and other vendor specialists (Oracle, SAP, IBM) on multi vendor engagements
• Contribute to thought leadership content (articles, webinars, client briefings) to build the Redress Microsoft brand

Qualifications

• 7+ years of hands on experience in Microsoft enterprise licensing (EA, SCE, CSP, MPSA, or equivalent)
• Deep knowledge of Microsoft 365, Azure, Dynamics 365, and Server/CAL licensing models
• Direct experience negotiating Microsoft Enterprise Agreements or Cloud Solution renewals with Microsoft or through LSPs
• Ability to conduct independent licensing assessments and produce client ready deliverables
• Familiarity with Microsoft compliance and audit processes
• Strong commercial instincts. You understand how licensing decisions connect to cost, risk, and vendor strategy
• Comfortable working remotely and managing multiple concurrent client engagements
• Excellent written and verbal communication skills. You will be client facing from day one
• Experience at a licensing advisory firm, SAM practice, or vendor side licensing team is strongly preferred

What makes this role different

You are not joining a large consultancy where you will be one of fifty Microsoft people. You are the Microsoft practice. You will have direct client relationships, work alongside the founders, and shape how we deliver Microsoft advisory at scale. We are building toward a significant exit within 24 months and this role is a key part of the growth engine. Compensation reflects the seniority and impact of the role.

We are seeking an experienced Risk Manager to join our Portfolio Operations team. This role will have firmwide responsibility for insurance and risk management across 15+ portfolio companies spanning multiple industries. This role will partner closely with portfolio company leadership to optimize insurance and benefit programs across the portfolio. The Risk Manager will drive cost savings while balancing appropriate coverage levels.

This is a highly visible, hands-on role suited for a professional who thrives in a fast-paced environment and can balance strategic oversight with execution.

Portfolio-Wide Insurance Oversight

• Manage renewal process for commercial insurance programs across multiple portfolio companies, including Property; General & Excess Liability; Auto & Workers’ Compensation; Cyber; and Management Liability (D&O, EPLI, E&O, Fiduciary).
• Establish portfolio-wide insurance standards, minimum limits, and coverage guidelines.
• Ownership of the renewal process to ensure competitive quoting well in advance of renewal timelines
• Review policies for coverage consistency, evaluating deductibles and limits, as well as benchmarking coverage against industry norms and operational risk profiles.
• Maintain policy documentation, certificates of insurance, and renewal timelines to prevent gaps and lapses.
• Support insurance diligence on acquisitions of new investments
• Prepare risk reports and review with company leadership as well as with Hidden Harbor leadership on a routine basis to develop transparency of insurance spend and claims trends.

Risk Mitigation & Program Optimization

• Assess enterprise and operational risks at multiple portfolio companies and recommend best practices to mitigate future risk.
• Track loss runs and claims trends; coordinate mitigation efforts with brokers, TPAs, and portfolio companies
• Lead escalation and resolution for high-severity or complex claims

Health Benefit Program Optimization

• Overseeing benefit programs to include analysis and acts as contact with providers (including group health, dental, vision, LTD, Life, etc.), workers' compensation, and retirement plans
• Partner with brokers, carriers, and portfolio company executives to manage plan performance, costs, renewals, and employee experience
• Analyzes aggregate health claims data to recommend and implement employee wellness initiatives based on claims to drive lifestyle and behavior changes which will lower claims and premiums for the future
• Partner with portfolio company executives to ensure success with the annual open enrollment planning, execution, and communications.

Broker & Carrier Governance

• Maintain relationships with various brokers and carriers to ensure consistent underwriting standards and service quality.
• Evaluate broker responsiveness, execution, and performance against risk mitigation objectives.
• Coordinate information flow between companies, brokers, and internal teams.

Qualifications

• 10+ years of experience in:
• Corporate risk management or
• Senior-level insurance brokerage or
• Risk advisory with direct program ownership
• Demonstrated experience managing multi-entity, multi-industry insurance programs
• Strong working knowledge of US commercial insurance markets
• Exposure to M&A transactions and insurance diligence preferred
• Comfortable operating in a hands-on, execution-focused role
• Experience in negotiating renewals and running competitive bid processes
• Proven ability to influence without direct authority
• Bachelor’s degree required; risk management or insurance designations (ARM, CPCU, etc.) a plus