Software built for the way you operate.

We design, build, and deploy custom solutions for mid-market companies — with the precision of a firm ten times our size, and none of the overhead.


Our approach

Mid-market companies deserve enterprise-grade software — without the enterprise price tag.

Better solutions

We don't sell templates. Every engagement starts with a deep understanding of how you actually operate — and ends with software built precisely for it.

Shorter timelines

We move fast without cutting corners. Our process is lean by design — no unnecessary layers, no bloated teams, no six-month discovery phases.

Lower costs

We are not a big firm. That's intentional. Our structure keeps costs lean and ensures the people selling you are the people building for you.

Not sure where to start? Neither are most of our clients.

We offer free, no-strings assessments for companies that have an operational problem but aren't sure what the right solution looks like. We'll listen, ask the right questions, and give you an honest read — whether we're the right fit or not.

Learn more

Free assessments

We come to you. We observe. We document. You keep everything.

Before any engagement, we offer a free operational assessment — no pitch, no obligation. We spend time understanding how your business actually runs, identify where software could make a meaningful difference, and hand you a clear-eyed report of our findings. The documentation is yours regardless of what you decide to do next.

01

Observe

We embed ourselves in your operation — in the weeds or as a fly on the wall, depending on what works for you. We learn how your team works, where time is lost, and where friction lives.

02

Identify

We map the operational inefficiencies we find — manual processes, disconnected systems, workflow gaps — and prioritize them by impact. No jargon, no filler. Just an honest picture of what's slowing you down.

03

Architect

We design potential solutions and document them in plain language. What it would take, what it would cost, what it would change. You walk away with a roadmap you can act on — with us or anyone else.

Always free

The assessment costs you nothing. No retainer, no hidden kickoff fee. We believe the right way to start a relationship is by providing value first.

You keep the documentation

Everything we produce during the assessment is yours. The findings, the architecture, the recommendations — no strings attached, regardless of what you decide.

On your terms

We adapt to how you operate. Some clients want us in every meeting. Others prefer we observe quietly and report back. Either way, we work around you — not the other way around.

Request your free assessment

Who we are

A small team that builds things that work.

Oakdale Solutions is a Chicago-based software consultancy founded on a straightforward premise: mid-market companies are underserved by the existing market. The big firms are too slow, too expensive, and too generic. The cheap options cut corners.

We sit in the gap — bringing enterprise-level thinking and execution to companies that have real operational problems and no interest in paying for overhead that doesn't benefit them.

Every solution we build is designed to be owned, understood, and extended by the people using it. We don't create dependencies. We create capability.

Theodore Iaccino
Co-Founder

Focused on business development, client strategy, and the operational vision behind Oakdale's engagements. Responsible for translating real business problems into technical solutions that actually get used.

Will Vesevick
Co-Founder

Lead architect and engineer. Designed and built Vesforce from the ground up, including its cloud infrastructure, CRM integration layer, and frontend. Responsible for technical execution across all Oakdale products and engagements.


Our services
01

Custom Software Development

From internal tools to client-facing platforms, we build software tailored to your workflows — not the other way around. Stack-agnostic, scalable, and built to last.

02

Systems Architecture & Design

We design the infrastructure behind the software — cloud, data, and integration architecture that performs under real-world conditions without unnecessary complexity.

03

Technical Strategy & Advisory

Not every problem requires a build. We advise on technology decisions, vendor selection, and roadmap planning — helping leadership make confident, informed calls.

04

CRM Integration & Workflow Automation

We connect your existing systems, eliminate manual processes, and build the workflow layer that sits between your tools and your team.


Our products
Sales Workflow Platform

Vesforce

A sales workflow platform purpose-built for mid-market teams. Vesforce sits on top of your existing CRM — or operates as your CRM — giving your team a cleaner, faster, more intuitive way to manage pipeline. Tailored to fit your process, not the other way around.

Category
Sales Operations
Deployment
Cloud · Self-hosted
Target market
Mid-market, $5M–$250M revenue
Status
Live in production
Coming soon

More in development

Every consulting engagement we take on is an opportunity to build something reusable. Additional products are in active development. Inquire for details.

Status
In development

Let's talk about what you're building.

Whether you have a defined project or an operational problem looking for a solution, we're happy to have an honest conversation about whether we're the right fit.

Location
Chicago, Illinois
Inquiries
hello@oakdalesolutions.io