Take your software into regulated markets. Then build the team that delivers it.

We help software vendors, carriers and banks turn AI, technology and growth choices into programs that ship. Short engagements. Senior people. Forty years in enterprise software, insurance and professional services.

Proof

$1M

First-year revenue for a 1.0 product at its first enterprise customer, a Canadian life insurer.

$2M+ ARR and 3 enterprise customers

For a Hong Kong software company entering the US and Canada.

$65M

Investor due diligence on an insurance brokerage acquisition.

What we do

Architecture is our largest practice. We connect business design, software, capital and market entry. Security, Finance and our pro bono Ethics practice support the work.

Design and build

Business and software architecture, AI strategy and governance, technology assessment and product planning. Make the important choices clear enough for people to build, test and operate the system.

Reach the market

Positioning, market selection, enterprise sales and go-to-market execution for vertical software. We connect the product, the buyer, the sales conversation and the delivery commitments.

Build the delivery organization

Professional services practice design: operating model, pricing, delivery methods, systems and hiring plans. Rob grew one practice from $1M to $15M and ran another at $20M.

Explore the services and starting engagements | Meet the four practices

Start small: Business Plan Assessment · Tech Stack in 2 Pages · IGNITE (Spark, Smart, Start) session

Recent work

2026

• AI strategy for a SaaS company serving legal operations.

• Professional services strategy for an organization-mapping SaaS company.

• Research on the tools of the frontier AI labs.

• A current program with Teleperformance, a global digital business services company that helps organizations improve customer experience and business processes.

2025

Continued advisory with the same partners under management.

2023-2024

• Two contracted proofs of concept with new technology at one of the largest banks in the world.

• Investor due diligence on software companies, including a $65M investment in an insurance brokerage and a $50M offer on another.

• Software sales lead for a 1.0 product and its first enterprise customer: $1M first-year revenue at a Canadian life insurer.

• Go-to-market and proxy GM for a Hong Kong company entering the US and Canada: three logos, $2MM+ ARR.

• Also: insurance product marketing for software companies, no-code data SaaS advisory, founder and funder matchmaking, pitch preparation, fashion-tech strategy and bootstrap consulting.

Explore selected work and case studies in preparation

Latest Weekly Signal

Ironstone Weekly. Three signals. Why they matter. What to watch next.

• The uncertain: AI risk is becoming a coverage argument

• The good: The semantic layer is becoming the product

• The hard problem: An agent needs an identity

Read the public issue | Explore Rob’s Substack

How we work

Two frameworks sit behind every engagement. TIE is why we work this way. SAFE is how we help.

TIE: why we work this way

Trust

We build trust through clear communication, empathy, transparency and the Chatham House Rule. Participants may use what they hear, but who said it is not shared. Our Security and Ethics practices turn those commitments into operating choices.

Innovation

Innovation combines people change, altered processes, new technology, recursive systems and idea creation. Our Architecture practice connects those pieces into systems people can understand and use.

Ability to Execute

Ideas matter when teams can finance, build, test and sustain them. Our Finance practice and Ironstone Methods connect futures thinking, resource development, financing, empowered ecosystems and durable infrastructure.

Trust maps to Security and Ethics. Innovation maps to Architecture. Ability to Execute maps to Finance and our Methods.

SAFE: how we help

Security

• Technical Security Stack Assessment

• Snap SOC review and assessment in 24 hours

• Security strategy summary for pitch support

Architecture

• Tech Stack Assessment and Design in 2 pages

• Interactive Innovation Tech Stack Workshops (2-6-2s)

• IGNITE (Spark, Smart, Start) Sessions

Finance

• 24 hour Business Plan Assessment

• Vertical TAM, SAM, SOM Assessment

• Financing Proposals and MOUs

Ethics

• 100-point Ethics Checklist for scale-ups

• Ethical Leaders Workshop

• AI governance advisory for software companies and enterprise companies

See how we work

Start a conversation

Book a 30-minute conversation with Rob about the decision, product or market you are working on.

Prefer email? rob@ironstoneadvisory.com.