Elevate your IT and finally get freedom to focus.

Are you constantly bogged down by the same IT issues, unable to focus due to endless interruptions? It’s time to break free from the cycle of mediocre IT. 

Discover how to get your IT from mediocre to great. 

No BS. Just Proper IT. That’s the Proper Way. Only from Proper Sky.


Proper Sky is a managed IT services provider (MSP) delivering IT solutions and IT support services to businesses across the Greater Philadelphia Area since 2006. Our ideal customers have real day to day technology needs and believe that maximizing worker and system uptime is the ideal way to drive down system costs.

Are you a small business (SMB) with 20 to 300 employees? Do you see technology as a competitive advantage and a way to differentiate your organization? Contact us to see if our services are a good fit for your business needs. We're here to help!

- 24x7 IT helpdesk support
- IT system management
- Cloud services (Microsoft 365 and Azure)
- Digital Transformation
- Cybersecurity management
- Compliance
- IT strategy and consulting
- Backup and disaster recovery (BDR)
- unified voice, telephony
- and more!

Industry: IT Services and IT Consulting
Company Size: 11-50 employees

Proper Sky - Managed IT Services

Savvy Admin PROD

**Why Work for Proper Sky?**

At Proper Sky, your work will make an impact from day one. As a small and agile team, we offer meaningful responsibility early on and continuous opportunities to grow, no matter your role. Every day brings fresh challenges and the chance to build new skills in a collaborative, fast-paced environment.

You’ll work closely with leadership and key stakeholders, gaining visibility and influence across the organization. Our team is made up of dedicated, mission-driven professionals who care deeply about delivering exceptional results for our clients and supporting one another.

We’re committed to your development and success. We provide leadership and professional growth opportunities through industry-leading programs like IT Nation, along with other third-party training and support. At Proper Sky, you’ll learn our systems, improve them, and bring value every day.

**About The Role**

The Virtual Chief Information Officer (vCIO) serves as the strategic technology advisor and executive partner to Proper Sky clients. This role owns the client-facing transformation process, translating business objectives into actionable technology strategies that reduce risk, improve operational maturity, and drive measurable outcomes. The vCIO operates with a seat at the table, leading C-level conversations and providing clear, forward-looking guidance on how technology investments align to each client’s strategic goals. This role partners closely with the Account Management Team, Alignment Team, Support Team, and Professional Services Teams to ensure that strategy is executable, measurable, and consistently delivered.

**What You'll Do**

**Strategic Advisory & Client Leadership:**

- Lead executive-level technology conversations with client stakeholders, including C-suite and senior leadership

- Translate client business objectives into structured, actionable technology strategies and multi-year roadmaps

- Provide ongoing technical thought leadership on emerging technologies, cybersecurity, compliance, and operational maturity

- Establish and maintain a strong understanding of each client’s business model, risks, constraints, and growth initiatives

**Technology Roadmap Ownership**

- Own the development, maintenance, and execution oversight of client technology roadmaps

- Ensure roadmaps are prioritized based on business impact and risk reduction

- Ensure roadmaps are financially aligned with client budgets and planning cycles

- Ensure roadmaps are structured for execution by internal teams

- Continuously refine roadmaps based on changing client needs, risks, and business direction

**Risk Management & Governance**

- Identify, assess, and communicate technical, operational, and cybersecurity risks with internal teams and strategic partners

- Provide clear remediation strategies with defined timelines and business impact

- Ensure clients have visibility into current risk posture

- Ensure clients understand progress toward remediation

- Ensure clients understand residual risk and trade-offs

- Drive accountability across internal teams to ensure risk-related initiatives are executed

**Quarterly Business Reviews (QBRs) & Client Governance**

- Own and lead all QBRs, ensuring they are structured, data-driven, and executive-relevant

- Present progress against strategic initiatives and roadmap execution

- Present risk posture and remediation progress

- Present service performance trends and key metrics

- Present alignment to business goals and upcoming priorities

- Present budget alignment and forward planning

- Ensure QBRs clearly communicate where the client is today, what has improved, what risks remain, and what actions are required next

- Facilitate occasional monthly governance touchpoints for high-complexity or high-priority clients

**Cross-Functional Alignment**

- Collaborate with the Alignment Team to ensure standards, configurations, and environments support the roadmap

- Work with the Support Team to identify trends, recurring issues, and opportunities for improvement

- Coordinate with the Professional Services Team to ensure successful execution of roadmap initiatives

- Engage the Finance Team to align budgeting, forecasting, and investment planning with client strategy

**Qualifications**

**Education & Experience:**

- 7+ years in IT leadership, consulting, or advisory roles within an MSP or similar environment

- Proven experience leading C-level and executive client conversations

- Strong technical foundation across infrastructure, cloud platforms, cybersecurity, and modern workplace technologies

- Demonstrated experience building and managing technology roadmaps and strategic plans

- Experience in risk identification, communication, and remediation planning

- Ability to translate complex technical concepts into clear business language

- Experience serving clients in Healthcare, Manufacturing, and/or Non-Profit industries is preferred.

- Familiarity with compliance and regulatory frameworks such as HIPAA and cybersecurity frameworks,, is preferred

- Experience operating within or alongside MSP service delivery models

**Soft Skills**

- Strong problem-solving and analytical thinking skills.

- Excellent written and verbal communication abilities.

- Ability to translate business needs into technical requirements.

- Highly organized, detail-oriented, and documentation-focused.

- Self-starter with a passion for continuous learning and process improvement.

- Collaborative mindset with the ability to work across multiple teams and priorities.

Virtual Chief Information Officer

The law firm of Kalikhman & Rayz, LLC is a legal practice focused on serving individuals and businesses in need of expert advice in southeastern Pennsylvania and the neighboring State of New Jersey. Dedicated to producing results, we pride ourselves on listening to our clients and providing creative legal guidance consistent with their goals and needs. Experienced in defending global insurance companies, large retailers, and manufacturers, our attorneys handle matters as varied as our clients, ranging from relatively simple issues to the most sensitive and complex commercial and insurance disputes. We are available for consultation whenever our clients call for assistance and are especially attentive to their needs in times of emergency.

Industry: Law Practice
Company Size: 11-50 employees

Kalikhman & Rayz, LLC

**About Us **

Kalikhman & Rayz is a growing personal injury firm in the Philadelphia region built on a simple mission: ~~be the injury firm where people are proud to refer their family members. ~~ We invest in our systems, technology, and people — and we need someone who can bring the same energy to our financial operations.

**The Role **

We are looking for a **financial controller ** with personal injury law firm experience to own our day-to-day financial operations and reporting. This is a hands-on, data-focused role. You will be the person working with financial data, building reports, and giving the firm's leadership a clear picture of the firm's financial health.

**What You'll Do **

**Financial Reporting & Analysis: **

- Build and maintain internal financial reports and metrics**.**

- Analyze financial data to identify trends, flag issues, and recommend next steps on financial projects.

- Provide the firm’s leadership with a clear view of financial health.

**Day-to-Day Financial Operations: **

- Own the firm's QuickBooks Online environment — create, maintain, and reconcile data daily, including maintaining the chart of accounts.

- Manage full accounts payable and accounts receivable functions, including invoice approval, vendor payments, collections, and aging reports.

- Develop, document, and enforce internal financial controls and policies to safeguard firm assets.

- Handle bank deposits and account reconciliation.

**Bookkeeping & External Coordination: **

- Perform hands-on, day-to-day bookkeeping with the long-term goal of bringing all bookkeeping functions fully in-house.

- Serve as the in-house conduit to our external accounting firm, progressively reducing the firm's reliance on outside bookkeeping while maintaining the relationship for tax prep and compliance functions.

**Payroll, Time Tracking & HR Administration: **

- Oversee payroll processing — ensure accurate, on-time payroll runs in coordination with our payroll vendor.

- Manage time tracking and PTO administration, ensuring data flows correctly to payroll.

- Handle employee reimbursements and expense reports.

- Support basic HR administration tasks as needed (benefits enrollment, onboarding paperwork, etc.) with our benefits administration vendor.

**Systems & Integrations: **

- Pull and reconcile data between Clio Manage (case data) and QuickBooks Online (financial data).

- Maintain and troubleshoot integrations between systems to ensure case-related financial data stays in sync.

- Work with the Operations Team to build and improve financial dashboards, reporting workflows, and recommendations for growth.

**Cash Flow & Budget Oversight: **

- Support cash flow forecasting and monitoring to ensure the firm can meet its financial obligations.

- Perform actual vs. budget variance analysis and present findings to leadership on a regular cadence.

**Financial Projects & Growth: **

- Take point on ad hoc financial projects: vendor cost analyses, compensation modeling, budget forecasting, and more.

- Identify process gaps and propose improvements — you are not just maintaining the status quo; you are building better systems.

- Help leadership understand the financial story behind the data so decisions are grounded in real numbers.

**What We're Looking For **

**Must-haves: **

- Strong familiarity with QuickBooks Online.

- Bachelor’s degree (accounting, finance, or similar program preferred).

- Intellectual curiosity and an inherent motivation to add value in a growing organization.

- Strong attention to detail and comfort with expertise with finance and accounting principles.

- Ability to independently identify data errors, trace them to their source, and fix them — not just flag issues for someone else to resolve.

- Experience working at a law firm (personal injury preferred).

- Ability to independently input, organize, and analyze financial data using a variety of tools.

- Comfortable with cloud-based tools, dashboards, and modern workflows.

**Nice-to-haves: **

- Certified Public Accountant (CPA) license.

- Certified Management Accountant (CMA) certification.

- Experience developing or improving internal financial controls.

- Experience coordinating with external auditors or accounting firms.

- Familiarity with IOLTA procedures and personal injury distributions.

- Exposure to payroll, HR admin, or operational finance.

- Familiarity with Clio Manage.

**You do NOT need to be: **

- A senior executive or seasoned CFO.

- Someone who has already "done it all" — we value learning speed and cultural fit over a perfect resume.

**Who Thrives Here **

The ideal candidate has worked at another injury firm, understands how finances work at the individual case level and can translate that to firm-wide outcomes, and is ready to own and grow this role. You are organized, curious, self-directed, and comfortable working through complex issues. You care more about getting things right than looking impressive. You are the kind of person who, when a report doesn't look right, digs into the data instead of ignoring it or forwarding it to someone else.

**Our Values **

- **Team over ego ** — we build each other up.

- **Own it from start to finish ** — we are accountable for everything we do.

- **We win for clients ** — everything we do serves the people we represent.

- **Honest and direct ** — good or bad, we acknowledge every situation and address it head-on.

**Compensation & Details **

- **Schedule: ** 20 hours/week (flexible scheduling available)

- **Location: ** Huntingdon Valley, PA (in-office preferred, hybrid considered)

- **Compensation: ** Hourly

- **Start date: ** Negotiable

Financial Controller

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