Principal, Cloud Strategy & Advisory

Trustedtech; United States; On-site; USD 170,000 - 190,000; Full time

Benefits offered by this job

Medical coverage

401(k) match

Paid vacation

Job summary

TrustedTech is seeking a Principal, Cloud Strategy & Advisory, to lead high-impact enterprise engagements shaping cloud platform strategy, modernization, and governance. The role blends executive storytelling with technical depth to translate architecture choices into business value and actionable plans.

You will guide clients on Azure, hybrid-cloud, security, FinOps, and operating models, partnering with architecture and delivery teams to turn strategy into measurable outcomes and scaled

Qualifications

• 8+ years in cloud strategy or digital transformation with client-facing roles.
• Strong knowledge of Microsoft Azure platform and infrastructure strategy.
• Experience leading executive discovery and creating roadmaps and business cases.
• Excellent executive communication to explain technical/financial tradeoffs.

Responsibilities

• Lead cloud strategy and transformation engagements.
• Facilitate executive workshops and discovery sessions.
• Translate findings into executive narratives and roadmaps.
• Define actionable, sequenced plans with clear outcomes.
• Partner with Solutions Architecture and Delivery to enable implementation.

Skills

Cloud strategy

Executive advisory

Enterprise architect

Stakeholder management

Public speaking

Job description

TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Our robust team of in-house, U.S-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program.

Prioritizing a people-centric mission, TrustedTech has transformed the Microsoft software licensing experience, giving IT professionals complete confidence in the success of their Microsoft investment.

Overview:

TrustedTech is seeking a Principal, Cloud Strategy & Advisory, to help build and scale our Advisory function while leading high-impact strategy engagements for enterprise and mid-market clients. This is a senior client-facing role focused primarily on cloud platform and infrastructure strategy: helping customers determine how Azure, hybrid cloud, security, governance, operating models, and modernization investments should come together to support business outcomes.

The Principal will operate at the intersection of executive strategy, cloud architecture, organizational readiness, and transformation planning. They will bring enough technical depth to challenge assumptions and shape credible roadmaps, while translating complex infrastructure and platform decisions into business cases, investment priorities, operating model choices, and actionable programs that executive stakeholders can understand and support.

This role is platform-first but not platform-only. The successful candidate should understand how cloud foundations enable broader priorities across Data & AI, analytics, application modernization, security, and Copilot, and know when to bring deeper specialists into the conversation. This is not a primary delivery execution role; it is an advisory and practice-building role responsible for shaping what clients should do, why it matters, and how to sequence the path from strategy into execution.

Responsibilities:

Executive Strategy & Advisory Engagement Leadership

• Lead cloud strategy and transformation engagements that connect customer business priorities to platform, infrastructure, security, modernization, and operating-model decisions.
• Facilitate executive workshops, discovery sessions, current-state assessments, and value-mapping exercises with CIOs, CTOs, CISOs, infrastructure leaders, application leaders, and business stakeholders.
• Translate technical findings into clear executive narratives, business cases, investment priorities, and outcome-based roadmaps that address cost, risk, resiliency, agility, security, and growth.
• Establish clear decision frameworks and recommendations that help clients move from broad transformation ambition to an actionable, sequenced plan.

Cloud Platform & Infrastructure Strategy

• Advise clients on Azure and hybrid-cloud strategy, including cloud adoption and migration, platform modernization, landing zones, identity, networking, security, governance, resiliency, backup and disaster recovery, and cloud operating models.
• Assess current-state infrastructure and platform capabilities, identify strategic gaps and technical debt, and define pragmatic target-state architectures and modernization roadmaps.
• Apply Microsoft Cloud Adoption Framework, Well-Architected Framework, Zero Trust, FinOps, governance, and security-by-design principles to shape recommendations that are technically sound and operationally sustainable.
• Help clients evaluate cloud economics, consumption strategy, cost optimization, technical risk, operating-model impacts, and sequencing decisions before major transformation investments are made.
• Maintain working fluency across Data & AI, Microsoft Fabric, Azure AI, application modernization, and Copilot so platform recommendations account for the broader technology strategy and future workload needs.

Organizational Readiness & Transformation Planning

• Assess organizational and operational readiness for cloud transformation, including governance, skills, processes, ownership models, support structures, and change impacts.
• Develop cloud operating-model recommendations covering roles and responsibilities, platform ownership, governance forums, financial management, security accountability, and the interaction between internal teams and managed services.
• Identify transformation risks and adoption barriers and create practical mitigation plans that connect technology recommendations to the realities of the client organization.
• Partner with Solutions Architecture and Delivery to ensure advisory recommendations can translate into feasible implementation programs with clear phases, dependencies, outcomes, and handoffs.

Advisory Practice Building & Offer Development

• Help define and mature TrustedTech's Advisory methodology, positioning, engagement models, and repeatable offers with an initial emphasis on cloud platform, infrastructure, migration, modernization, governance, and operating-model strategy.
• Create reusable assets such as executive assessment frameworks, maturity models, workshop materials, strategy templates, business-case models, roadmap formats, executive readouts, and transformation playbooks.
• Establish quality standards for advisory deliverables so engagements consistently produce executive-ready outputs that lead naturally into actionable next steps.
• Capture lessons learned from client engagements and market feedback to continuously refine offerings and identify where additional advisory capabilities should be developed.
• Mentor architects, consultants, and emerging advisory talent on executive discovery, strategic framing, business-value articulation, and consultative engagement techniques.

Business Development & Strategic Pursuits

• Partner with Services Sales, Account Management, Acquisition Sales, Solutions Architecture, Delivery, and Microsoft field teams to identify and shape advisory opportunities early in the customer lifecycle.
• Support pursuit strategy, executive discovery, proposal development, scope definition, and statements of work for advisory and transformation engagements.
• Recognize opportunities to expand advisory engagements into broader Professional Services and Managed Services programs while maintaining a customer-outcome-first approach.
• Represent TrustedTech's advisory point of view in customer executive briefings, Microsoft engagements, workshops, webinars, and other market-facing forums.

Required Skills & Qualifications (must-haves):

• 8+ years of experience in cloud strategy, technology advisory, consulting, enterprise architecture, or digital transformation roles, with significant client-facing responsibility and a track record of shaping complex transformation programs.
• Strong knowledge of Microsoft Azure platform and infrastructure strategy, including migration and modernization, landing zones, networking, identity, security, governance, resiliency, backup, and disaster recovery, and cloud operating models.
• Demonstrated experience leading executive discovery and strategy engagements and translating technical findings into business cases, investment priorities, target-state roadmaps, operating-model recommendations, and measurable outcomes.
• Strong working knowledge of Microsoft Cloud Adoption Framework, Well-Architected Framework, Zero Trust, FinOps, governance, resiliency, backup, and disaster recovery, and cloud operating models.
• Working knowledge of Data & AI, Microsoft Fabric, Azure AI, application modernization, and related Microsoft capabilities, with the ability to connect platform strategy to broader technology priorities and engage specialists where deeper expertise is required.
• Exceptional executive presence and communication skills, including the ability to facilitate senior stakeholder conversations, challenge assumptions constructively, and explain complex technical and financial tradeoffs in clear business language.
• Experience developing executive presentations, strategic assessments, roadmaps, value frameworks, and other client-ready advisory deliverables.
• Strong consulting and project leadership skills; able to structure ambiguous problems, manage multiple stakeholders, drive decisions, and maintain accountability for engagement quality and outcomes.

Preferred Skills & Qualifications (nice-to-haves):

• Prior experience in a Microsoft partner, systems integrator, Big 4, management consulting, cloud advisory, or managed services organization.
• Relevant Microsoft certifications such as Azure Solutions Architect Expert, Cybersecurity Architect Expert, Azure Administrator, Fabric Analytics Engineer, Azure AI Engineer, or comparable role-aligned credentials.
• Experience with cloud economics, FinOps, business-case development, organizational readiness, operating-model design, or change-management frameworks.
• Experience advising customers across multiple industries and adapting cloud transformation priorities to different regulatory, operational, and business contexts.
• Experience shaping or launching consulting and advisory offerings, methodologies, intellectual property, or reusable client-delivery frameworks.
• Familiarity with Microsoft assessments, funding programs, partner-led workshops, and co-sell motions.

What Success Looks Like:

Performance in this role is evaluated against the advisory impact, practice-building contribution, commercial influence, and client outcomes expected of a Principal, Cloud Platform Strategy & Advisory at TrustedTech:

• Clients receive clear, executive-ready cloud strategies that connect platform and infrastructure investments to measurable business outcomes and an executable path forward.
• Advisory engagements consistently translate into well-sequenced transformation programs across Professional Services, Managed Services, and adjacent Microsoft solution areas where appropriate.
• TrustedTech develops a repeatable, differentiated cloud advisory motion with reusable assessments, frameworks, executive readouts, roadmaps, and playbooks that can scale across the organization.
• Solutions Architecture and Delivery teams receive clear strategic context, priorities, assumptions, and intended outcomes, reducing the gap between advisory recommendations and technical execution.
• Customer executives and Microsoft field teams increasingly view TrustedTech as a strategic transformation partner, not only a licensing or implementation provider.
• The Advisory function expands over time with clearer methodologies, stronger internal talent, and additional domain capabilities built on a consistent strategic foundation.
• Operating Hours: 6:00 am to 3:00 pm PT OR 7:00 am to 4:00 pm PT
• Estimated Salary Range: $170K - $190K + variable bonus (*DOE)

• 100% employer-paid base medical coverage: HMO (CA) | PPO (out-of-state)
• Dental and vision coverage
• 401(k) with 4% company match (fully vested)
• Paid vacation, sick leave, and holidays
• Paid parental leave
• Voluntary benefits (STD*, life/AD&D, accident, critical illness, hospital)
• Employee Assistance Program (EAP)
• (*Short-term Disability available for employees outside California)

*TrustedTech is an equal opportunity employer and does not discriminate on the basis of race, color, religion, sex, age, national origin, veteran status, disability, sexual orientation/gender identity, or any other characteristic protected by applicable law.*