Technology Strategy

Invest in the right solutions, in the right order.

Your projects are multiplying, and so are your technology options. We help you decide what to improve, what to buy or build, and how to move forward with your budget, teams, and business priorities.

An initial conversation to understand the decisions ahead and your business context.

  • Priorities tied to your goals
  • Options compared and choices explained
  • A roadmap for taking action

Practical decisions

Move forward when several paths are possible.

A new ERP, an AI initiative, a product launch, or tools to modernize: every choice commits time, money, and your team. We make the options and their implications clearer.

Prioritize technology investments

Every department has requests: CRM, automation, AI, data, new tools. Your budget and delivery capacity cannot support launching everything at once.

How we help

We compare initiatives by expected value, effort, risk, and dependencies. You get a delivery sequence, the reasoning behind it, and criteria for measuring progress.

Choose between buying, adapting, and building

Several vendors promise to meet your needs. You need to compare licenses, integrations, product limitations, and the cost of custom development.

How we help

We clarify requirements and assess options by total cost, fit with your processes, and ability to evolve. A demonstration or pilot can validate uncertainties before you commit.

Plan how your systems will evolve

Aging tools, scattered data, or fragile integrations slow the business down. You need to decide what to keep, improve, or replace.

How we help

We map applications and data exchanges, identify constraints, and propose a target architecture. The transition is broken into stages that account for business continuity.

Align your team and partners

Technical decisions depend on a few people, responsibilities are unclear, or several vendors are working toward different priorities.

How we help

We clarify roles, decisions to resolve, and delivery criteria. Part-time technology leadership, or fractional CTO support, can help your team within an agreed engagement.

Business, processes, and technology

Business and technology expertise to guide your decisions.

With a BTech in software engineering, Orléando combines experience in solutions architecture and technical leadership with studies in management and process improvement. This combination helps connect your business priorities with technology decisions.

Automathing’s two founders work with consultants, partners, and your teams according to the engagement’s needs. The analysis accounts for the people who will put the decisions into practice.

Meet our team

Orléando Dassi’s background

BTech · MBA ’27 · Six Sigma Green Belt

BTech · Software Engineering

A Bachelor of Technology in software engineering that underpins his work in development, systems integration, and solutions architecture.

MBA · Université de Sherbrooke

In progress · expected completion in 2027

Studies focused on strategic thinking, innovation leadership and organizational management, pursued alongside his professional work.

Six Sigma Green Belt

Training in process improvement that complements his approach: understand how work happens today, investigate the causes of problems and define how to measure progress.

Architecture and leadership in large organizations

Before Automathing, Orléando contributed to projects for BRP, VIA Rail, and WADA in his roles at CGI. These contributions are part of his prior professional experience and were not Automathing engagements.

CGI · 2024–2025

BRP

Participation in the architecture design committee and coordination across delivery teams.

Explore the contributions

CGI · 2022–2023

VIA Rail

Day-to-day leadership of 15 consultants, technical coaching and code reviews.

Explore the contributions

What you get

Documented decisions and a usable plan.

Deliverables are defined at the outset around the decision you need to make. They give leadership a basis for choosing and your team a basis for preparing the next steps.

A decision brief

The need, options considered, assumptions, estimated costs, and risks. The recommendation explains trade-offs and what still needs to be validated.

A prioritized roadmap

Sequenced initiatives, dependencies, milestones, and effort or budget ranges. Immediate actions are distinguished from investments that need preparation.

An execution and review framework

Responsibilities, success criteria, and decision points. Your team gets a basis for consulting vendors, launching a pilot, or planning delivery.

Methods that inform your choices

We use the analysis tools relevant to your decision. Platforms and technologies are assessed for their value to your business.

Value and prioritization

Compare expected benefits with effort and capacity for change.

  • Impact · effort
  • Process mapping
  • Success measures
  • ROI assumptions

Options and total cost

Evaluate a solution beyond its purchase price.

  • Buy · adapt · build
  • Selection scorecard
  • Total cost of ownership
  • Vendor assessment

Architecture and risk

Understand dependencies and prepare a realistic transition.

  • Application mapping
  • Data flows
  • Risk register
  • Architecture decisions

Planning and governance

Turn choices into steps and responsibilities.

  • Roadmap
  • Milestones and dependencies
  • Roles and responsibilities
  • Decision reviews

We distinguish observed facts, estimates, and assumptions to test. Expected benefits are reassessed against results in practice.

Your questions about technology strategy

Who is this service for?

Business leaders, operations managers, IT teams, and product leaders facing a significant technology decision. You may have an internal team, work with vendors, or be preparing your first project. We adapt the engagement to the people and decisions involved.

How does this differ from a business diagnostic?

A diagnostic helps surface problems and opportunities for improvement across your organization. Technology strategy defines system choices, investments, priorities, and the delivery plan. A diagnostic can provide the starting point, but we can also work from an existing assessment.

Can you help us decide where to use AI?

Yes. We start with an operational need and evaluate available data, expected benefits, costs, risks, and adoption. We compare AI with other options, such as an integration or conventional automation, then define what a pilot needs to validate.

Do we have to hire you for development afterward?

No. The engagement can end with recommendations and a roadmap. Your team or another partner can implement them. If Automathing participates in delivery, its scope and terms are covered by a separate agreement.

How do you work with our IT team or technology lead?

We involve them in assessing constraints and options. Roles and decisions are clarified together. Fractional CTO support can complement your leadership capacity on specific issues, with availability and responsibilities defined in the engagement.

How long does an engagement take, and what budget should we expect?

It depends on the number of decisions, systems, and people to consult, as well as the quality of available information. We clarify deliverables, required access, timing, and budget before starting. You can begin with a focused decision and expand the engagement if needed.

Your next decision

Which technology choice is blocking your next step?

Tell us about your goal, the options you are considering, and your constraints. We can define the analysis you need to decide and move forward.

An initial conversation to understand the decisions ahead and your business context.

Based in Sherbrooke, we support teams in Quebec and beyond, in French and English.