Technology strategy for the next stage of your business


Technology should support the business. Waypoint Business Solutions provides strategic guidance, technology planning, and executive advisory services that help organizations make informed decisions and execute with confidence in an ever-changing business environment.


Not sure where your next business technology waypoint is?

Let's talk!

The Waypoint Approach

A CLEAR PATH FORWARD


A waypoint marks progress on a journey.

A waypoint helps you understand where you are, where you are headed, and what comes next.


My role is to help organizations establish direction, evaluate options, and move forward with confidence through thoughtful planning, informed decision-making, and practical execution.

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Guiding Principles

Simplicity

The best solution is the one that people can actually maintain

Practicality

Recommendations should be realistic, actionable, and deliver value

Partnership

Success comes from working collaboratively and building trust over time

Continuous Improvement

Small, deliberate improvements compound into meaningful results

Services

Waypoint Business Solutions offers the following services to help organizations understand where they are, determine where they want to go, and build the path to get there.

Business & Technology Strategy

Strategic advisory services designed for organizations that need executive-level technology guidance.


Services include:

Business and technology assessments
Strategic planning
Technology roadmaps
Vendor and contract review
Budget and investment planning
Executive advisory
Quarterly business reviews


Expected Outcomes:

Clear technology direction
Improved visibility into risks
Better investment decisions
Reduced technical debt
Technology aligned to business priorities

Fractional CIO Services

Executive-level technology leadership on a part-time basis.


Ideal for organizations that:

Have internal IT staff
Work with an MSP
Are growing quickly
Need strategic technology leadership

Services include:

Technology planning
Executive reporting
Risk reviews
Governance guidance
Vendor management
Technology budgeting
Leadership support

Technology Initiatives & Projects

Supporting organizations through significant business and technology changes.

Examples:

Microsoft 365 initiatives
SharePoint solutions
System migrations
Process improvement efforts
Technology evaluations
Implementation oversight

About

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Dave Whalen

Founder
Business & Technology Strategist

Hey! I'm Dave


I started as a technical contributor, but repeatedly found myself drawn to the business problems surrounding the technical work. Over time, that took me from data analysis into business operations, finance, IT management, and cybersecurity. Along the way, I kept building and configuring systems to make those functions work better.

I’ve managed IT teams, worked closely with managed service providers, and led the development of a cybersecurity program that secured operations and passed a DIBCAC High Level Assessment.

Those experiences shaped how I approach problems today: I think like a business manager, but I still have the technical depth to understand how the systems underneath the business actually work. My approach is practical, risk-aware, and focused on business value.

Outside of work, you may find me enjoying a cup of coffee at a local café, playing disc golf, or spending time with my family.

Contact

A clear path forward starts with a conversation. Connect virtually or over coffee to discuss your business, technology, and opportunities for improvement.