Build the business. Win the work. Deliver.

I help founders and leaders build companies that work. At Ironstone Advisory, that means designing the business, building the software and the organization around it, and getting what you've built into a market that will pay for it. I work with CEOs and CTOs who need someone able to connect the commercial decision to the technical work. Sometimes we are building the next professional services organization. Sometimes we are sharpening an offer, growing a sales funnel and doing the work to win customers. Increasingly, we are putting agentic systems into professional services, sales and marketing. I founded the firm in 2019, based in Toronto and working across Canada and the United States. What will make the business work better, and how do we get it done? That is where we start.

I have helped start or scale more than a dozen companies, including companies I founded. My degree is in computer science and statistics, and I've been doing professional IT work since 1982. That background shapes how I work as a designer and business architect. At NexJ Systems, I grew professional services from $1 million to $15 million. I've run organizations of developers and consultants delivering client projects, effectively software companies inside software companies, with their own customers, delivery obligations and economics. Ironstone has also helped a Hong Kong software company enter Canada and the US, reaching three enterprise customers and more than $2 million in annual recurring revenue. Founding a company means bringing a product to market, giving customers a reason to buy it and building an organization that can deliver. All of it has to work together.

My philosophy of business is Energy, Principles, Intellect and Courage. Bring the energy to get moving, the principles to handle people's trust and information properly, the intellect to question your own assumptions, and the courage to make a decision and take responsibility for it. Execution is everything. I see it as the ultimate test of governance, along with profitable revenue: what actually gets done, what customers receive and whether the business can sustain it. You work directly with me, and I bring in the capabilities the assignment needs. We agree what needs to change, build and test, and judge the result against the business we are trying to create. Bring me the problem while it is still untidy. We can work out where to begin.

Book a conversation

Three ways we can work together

Building Your Next Professional Services Organization

Build a services business that customers want to buy from and your people can deliver.

Whether you are launching a practice or changing an established one, we work on the offers, economics, delivery methods, roles and systems together. Agentic systems belong where they improve the work, with clear responsibilities for the people using them.

Start with a practical design for the organization and the first changes needed to make it work.

Explore professional services practice design

GTM: Grow Your Funnel and Execute Lab

A larger contact list is not the same as a better sales funnel.

We help you understand the market, choose the accounts that matter and give buyers a reason to act. Then we work with you on campaigns, sales conversations and follow-through. Our Market Map Method and the Marketing Mapper concept connect market research to practical decisions about where and how to compete.

Start with one offer, one target market and a focused set of tests.

Explore the Market Map Method · Discuss a GTM Lab

Making Your Operation Agentic

Put agentic systems inside useful work, with people accountable for the result.

We help you choose a workflow, connect the information it needs and define what an agent may do. Then we build and test a bounded implementation against the way the work happens today. The model matters. So do the architecture, permissions, exceptions and person who owns the outcome.

Start with a workflow worth improving and evidence of what would count as an improvement.

Explore agentic systems

Experience behind the work

Professional services leadership

At NexJ Systems, Rob grew professional services from $1M to $15M. He also led professional services at BOLT Systems and global insurance business development at Salesforce.

Market entry and enterprise sales

Ironstone's work includes helping a Hong Kong software company enter the US and Canada, reaching three enterprise customers and $2M+ ARR. A separate engagement brought a 1.0 software product to its first enterprise customer, a Canadian life insurer, with $1M in first-year revenue.

Systems we are building

Our current development work includes NeoLibrary, the Ironstone Brain Library and NeoCRM. These projects inform how we design business memory, relationship intelligence and governed agentic systems. They are works in progress, not finished products presented as client results.

Explore our work · About Rob

Our investment work also includes investor due diligence on a $65M insurance brokerage acquisition. This is the transaction value, not Ironstone revenue.

Recent engagements and history · Insurance software market entry

Thinking from the work

Field Notes & Essays explores what we are learning from software, markets and building things. Weekly Signal connects developments in technology, politics and economics, because the interesting questions rarely stay inside one category.

Field Notes & Essays · Latest Weekly Signal

Latest Weekly Signal

October 30, 2026: Who carries the risk? Five connected articles at the intersections of technology, politics and economics, plus two further readings added November 1.

• Read the risk factors before the valuation

• The cost of capital is back in the room

• Identity becomes an implementation problem

• A useful boundary in insurance claims

• More agents can mean more agreement, not more evidence

Also: Ray Kurzweil's digital twin and Codex Micro, the custom keypad from OpenAI and Work Louder for agentic work.

Read the public issue | Explore Rob's Substack

How we develop the work

The Creation Model guides how we develop the work. Thinking, making, testing and judging feed back into one another. We keep the evidence and learning so the next decision has something better to stand on.

Architecture is our largest practice, supported by Security, Finance and our pro bono Ethics practice.

The Creation Model · Ironstone Methods

Architecture · Meet the four practices · Services and starting engagements

Our starting offers include the Snap SOC review and assessment in 24 hours, the 24 hour Business Plan Assessment, Tech Stack in Two Pages and IGNITE (Spark, Smart, Start) sessions.

Explore what we do · Complete site index

What are you trying to build or change?

Bring the problem, even if the brief is not finished. Book 30 minutes with Rob to discuss where the work could start.

Book a conversation · rob@ironstoneadvisory.com