Aaron Vidas

Safe AI for more customers, profits + time

I’m an AI + ML entrepreneur who’s spent 15+ years founding and scaling 4 big data, strategy, and AI companies; including a VC-backed global data platform. In 2024 my Life split in two: one week I was marathon training; the next I was told “Prepare not to see the end of the month” because of a brain tumour.

What followed was a chain of miracles, a full recovery and level of clarity that changed how I lead.

Today, I helm DASS Services, the world’s fastest-growing AI consultancy. And DASS Group an AI-enabled holding company acquiring extraordinary businesses across the world.

I build companies that create outsized impact, and a lot of joy, along the way.

HOW I HELP

I work with luxury travel groups, building-supply companies, wellness brands, and professional service firms generating $5M–$2B+ in annual revenue to:

• Unlock their first “AI Win” in 90 days so they build belief in AI's actual capabilities 
• Help Founders, Boards, and CxO’s deploy capital, hire, lead, and succeed in the AI Age
• Build enduring companies whose value grows exponentially as ai-enabled systems take over
• Acquire exceptional businesses and elevate them through AI, process intelligence and elevated consciousness

If you want clarity, speed, and ROI in this new era, happy to talk.

WHAT I SHARE HERE

• The AI playbooks behind our average 787% ROI in 1–8 months on AI projects
• What’s real vs. hype in the AI Age
• How-to lead confidently while the world shifts beneath our feet
• How-to build extraordinary companies while staying vibrantly, fiercely alive through the highs and lows of Life

YOUR NEXT STEPS

Want your first AI Win in the next 90 days?

Grab the 90-Day AI Win Playbooks for your industry below and see how companies are unlocking profit, time, and joy through AI-enabled systems.

Then take a visit to dass-services.com 

Want an AI Workshop for your Board or C-suite?
Want me to speak at your event?
Want to explore a partnership or acquisition?

Visit aaronvidas.com

Founder

The first question I ask AI Strategists and AI Engineers I'm hiring? "Walk me through what you've built." 

I'm looking for: 

- How they discovered where AI would be leveraged best in a work process. Usually by it doing the 'boring and tedious' (like downloading info from one software platform, massaging it in Excel and uploading it to another) or providing insights, and information, that would normally take hours/days of analysis so better actions can be taken, creating better outcomes. 

- How they trained staff doing the work daily and overcame objections like "well, the way we've already been doing works for me." 

- How they chose the tools they did to maximize performance, minimize cost or minimize time to value. 

- How they set up monitoring, maintenance and how the AI workflow will live on without them.

If they show a beginners mind to spot bottlenecks, empathy in training and technical acumen to do the above you know you've got a successful AI expert on your hands. 

Courses, credentials, college degrees and "20 years in machine learning" doesn't matter in 99% of generative AI use in business today. The technology's curves are too new for institutions to have caught up and translated that into formal, credentialed learning. 

What you're looking for is passionate people who have learned on their own and translated that into their every day and served others. 


#ai #privateequity #vc #aijobs #singapore

Notion isn't working for me and my team any more. What's everyone using to store ideas, SOP's, content, client work and finance data?

My vision is a flexible database I can stick Lyzr AI, Glean and Vertex Inc. on top of for search to agents doing marketing to financial analysis with a decent UI/UX a non-technical person can input data and find info they need from my content rants in WisprFlow to client's Service Agreements. 

Sara, Reuven, Allie, Wayne what are you using these days? 

#ai #aiengineering #singapore #aijobs

Amazing at surfacing processes, and decisions, and designing #AI-enabled systems that do the boring and tedious? 

Also, a wiz with ClickUp? 

Trolley AI hiring for your dream job. 

Surfaced by the awesome DASS Services NA Job Monitor 

#yvrjobs #aijobs #remotejobs

Open article: Senior AI & Systems Lead | Trolley by trolley-2.careers-page.com

My friend Steve Krueger has created some special for mid-size retail brands. We know AI provides the ability for people to have vastly different interactions with their favourite brand. New forms of content, shopping experiences, one-off sites and communities. But how do you actually manage that, no less build it? 

That's what Compass Commerce has done. From making content to storefronts for 2026 and beyond. All in one spot. 

Good people doing great work. Congrats Steve!


#ai #ecommerce #privateequity #vc

Crafting beautiful ecommerce experiences for better-life brands. | 7x founder | Investor | CEO/Founder @ JIBE 🚀 ECOMsquare 🏠

25 years into my career, 17 years of JIBE, and 6 years building toward this. The world is entering a period of massive change. With that comes volatility. And with volatility comes opportunity. That’s what has me fired up for what’s ahead.

Six years ago we had a theory that consumers would transact in completely different ways than they do today. At the time, we started seeing glimpses of it as companies, like Amazon, experimented with new commerce experiences that felt incredibly future forward, but completely out of reach for most brands to actually build.

That curiosity pushed us to look deeper. We realized the current technical landscape wasn’t built for the pace of change coming, so we leaned into composability. The belief was simple: systems that are modular and flexible give brands the best chance to adapt quickly as the world accelerates.

Fast forward to today, and that acceleration is everywhere. AI, new channels, new expectations. Leaders are trying to make sense of it, and teams are feeling the pressure. 

The gap between the people who understand the systems and the people who don’t is also widening quickly.

The biggest challenge businesses face today isn’t access to tools. It’s making sure the ability to use them is available to everyone on the team. 

That’s what Compass Commerce is about.

What feels like the culmination of the last six years, and honestly much of my career, has been built into what our team at JIBE – building composable ecommerce experiences has been building.

Compass connects the messy reality of a modern commerce stack and turns insight into action so teams can ship faster and adapt with confidence.

At its core, Compass helps teams move from signal to execution.

📈 Signals pull insights from across your commerce stack including ERP, CMS, storefront, marketing and analytics.

🧠 Knowledge brings your personas, brand guidelines, and your durable business context to keep your brand, segmentation, business rules, and KPIs in check.

🛠️ Skills are modular agents that turn those insights into reviewable outputs.

🕸️ Surfaces ship updates directly to the places customers interact with your brand such as storefronts, content, and marketplaces.

The goal is simple. Help teams ship weekly instead of quarterly, adopt new technology safely, and bring everyone along for the ride.

The waters ahead are moving fast. None of us have a perfect map, but we believe the best way forward is to sail it together. The crew is assembled, the sails are up, and the voyage has just begun. We are proudly crafted in 🇨🇦 

Follow along at Compass Commerce.

https://lnkd.in/gv5GtA_F

#futureofcommerce #commerce #commerceai #compasscommerce

Shoutout to Alex Chee with their ForceMultiple GTM credit product. A way for Founders, and the lender, to shoulder risk of acquiring cohorts of customers without the fixed burden of a more traditional ARR-based lending agreement. 

#founder. #ai #saas

CEO at Termina, Co-founding Partner at Tribe Capital

Friends, excited to share ForceMultiple, our GTM financing product at Tribe Capital is LIVE! If you're a founder, we're OPEN!

Over the last few years, Jake Ellowitz and I have seen a consistent pattern across the thousands of companies analyzed through Termina Systems, Inc.: when unit economics work, the bottleneck is working capital. GTM creates a terrible TROUGH — cash goes out today, collections arrive months later. In a tighter equity market, that trough constrains growth, forces trade-offs with R&D or forces dilution.

I've seen this tragedy unfold at EVERY company, and each time, the result is a journey filled with blood sweat and tears. From Lolapps with Kavin Stewart and Kamo Asatryan, to MessageMe with Arjun Sethi, to Joist with Justin Kathan and Brendon Sedo.

As promised, we're here to help folks ELIMINATE that trade-off. We'll work with you to fund your cohorts, so you can focus on growing your business, without all the downsides we've all had to go through.

Interesting? I think so. If you think so too, shoot me a message and we can dig in together.

Open article: Introducing ForceMultiple - Tribe Capital by tribecap.co

Introducing ForceMultiple - Tribe Capital

Event experts in AI get gobsmacked by its abilities daily. We're rebranding DASS Services NA and the team was able to build a new brand identity, standards and component library in a workday. 

While working around the Olympics I built dozens of brands from scratch. #ClaudeCode built what would take dozens of people 8-12 weeks, and hundreds of meetings collectively, just by us giving the LLM's feedback along the way.

This foundation will allow our agents to build 100K's pieces of content, 10K's of microsites, 1K's of ad variations, for us (all while remaining 'on-brand') over the coming months. Because everything is designed for an ai agent to read. 

What I loved most about the project? We could exercise our judgement, and experience, concisely and get something that resonates while we focused on the fun stuff: talking to customers and thinking about weird, valuable ways to leverage AI at work for more time, profit and energy. 

#ai #privateequity #familyoffice

If you want to be hiring great people to implement AI within your company, fund or family office, copy Wealthsimple’s approach. 

Ask people what they’ve built that has AI ‘think’ on its own and produce an outcome in a business process. Ask them to show you how it traces producing that outcome and how it protects customer and company information. 

In 2026 you can’t rely on degrees, certificates or programs to be markers of competence with AI. The bottlenecks are not knowledge. It’s people putting their hands on the tools and having the emotional intelligence, and business acumen, to make something work well. That’s the sign they’ll thrive in your businesses.  

#privateequity #ai #singapore #yvrjobs #familyoffice

We're trying something new at Wealthsimple.

Today we're launching AI Builders — a non-traditional hiring process for a small group of cross-functional builders who want to rethink how work gets done.
No resumes. No minimum experience.

Instead: build and demo a working AI system that meaningfully expands what a human can do. Not AI layered onto old workflows — AI-native systems designed from scratch, with sound judgment about where AI should own the work and where humans need to stay in control.

We'll review every submission within 48 hours of close. Interviews and offers happen the same week.

If you look at legacy systems and think, "This wouldn't exist like this if we built it today" we want to hear from you.

Open article: Wealthsimple AI Builders by wealthsimple.com

A genuinely fascinating looking job if you're passionate about #ai and #health in Ontario. 

#aijobs #aistrategy

Executive Vice President, Performance and Planning & Chief Information and Analytics Officer | Driving Strategy, Digital Transformation & Data-Driven Health System Innovation

The potential of AI is extraordinary. But the real challenge — the hard, meaningful challenge — is figuring out how to deploy it in ways that actually matter. Especially in an environment as complex, high-stakes, and deeply human as healthcare. 

That is the problem our team at Trillium Health Partners is focused on. Not AI for its own sake, but AI designed for human-centred impact — the kind that helps someone living with a chronic disease stay well and out of hospital, that removes friction from the work of a care team, that makes a complex system feel more connected and responsive to the people it serves.

To do this well, we need to bring together the right skills and experience alongside our incredible teams. With that in mind, I am recruiting for a Chief AI and Digital Planning Officer — a newly created role with a mandate to close the gap between what AI promises and what it actually delivers.

What I can offer the right person is an organization that is genuinely ready. Executive commitment, a community that wants to solve these problems, a landmark infrastructure renewal underway, and a team already doing serious work. You won’t be starting from zero. You’ll be accelerating something that has real momentum.

If you are driven not just by building powerful technology, but by the harder and more important question of how we make it work for real people in real systems — this role is for you.

Less “Here are the four things I learned after a small flight delay” and more plunge into a cold ocean and contemplate how amazing it is to be alive right now.

#leadership #ai #familyoffice #privateequity #consciousai

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The ‘jagged edge’ of AI is exactly that. It will astound you and utterly frustrate you in the same hour. You discover the limits by doing. 

For example last night several agents created 78 markdown files, and few thousand lines of code, all for my CEO OS system (a process, and app to organize my businesses and Life so I can stay in flow states) all while I stretched before bed. That would normally be ~3 weeks of an FTE software developer's time designing and building. 

This morning I asked Claude Cowork to rename a couple dozen folders on a Google Drive and my laptop. And move them around so the CEO OS knows where to look for certain information and set about my morning meetings. 

4 hours later Claude was still banging away at trying to create the folders. Manually, a 10 minute job. 

It’s a reminder that we’re very much in the infancy of AI and it’s okay for the technology to certain tasks extremely well and others less so. 

That doesn’t mean it’s ‘all bad’ or ‘all good.’ And it doesn’t mean that AI’s capabilities are fixed. 

Quite the opposite, who could have predicted 18 months ago I, a non-coder, could create apps, and systems, that would normally take $1M’s in overhead to create and manage? 

It just means you explore, experiment and double-down on uses where it creates a lot of leverage today. 

Accepting what isn’t working today and checking back periodically to see if AI can now do the task. 

Because that’s where incredible growth happens.  


#ai #privateequity #vc #familyoffice  #singapore

I'm using Claude Skills, and markdown file-based instructions, a lot more than I thought I would to run my business. It's how I see a lot more businesses getting started with AI inexpensively and quickly. 

If you didn't know, Claude has created an elegant way to store explicit instructions on what the AI is to do, what it 'looks' at and the actions it then takes. They call it 'Skills.' You type a specific command in the chat and it starts the process stored in the skill to give you an outcome.

For example, on Fridays I do a Weekly Review of myself and business. It's 20 questions and reviewing of KPI's and financials. I type "Let's do my Weekly Review" and it knows what all the questions are, where to find the appropriate financial info and links to it. Plus, my answers are stored in a database. 

What would be a 1.5 hr process of seeing where I, and my company, is at takes 20 mins. More importantly, an 'AI Aaron' spots patterns repeating over time in my behaviour, and limiting beliefs, and points them out so I can maximize my impact.

I now have 'skills' for creating content; onboarding clients and employees; performing analysis; and managing projects. 

I thought this was all going to require an elaborate agentic management infrastructure. Turns out you just require a Claude Pro subscription and the decision to write down how stuff gets done in your business. 

You're first step in building skills? 

Just pick a boring and tedious task you have to do to keep the lights on and write down how it gets done. Then ask Claude to help you build a skill to do the boring and tedious parts (look up information, put together a presentation, fill out a financial model, etc.) and you're on your way.


#ai #familyoffice #privateequity #aijobs

Are you a full stack AI dev looking to have a lot of fun in the last decade of software development? Stuart Bowness and his team are cooking up something cool.

#yvrjobs #ai

Co-Founder | Building Toyo - AI agents for Founders

We're hiring a founding AI engineer at Toyo.

Toyo is the agent platform for small business. Founders and their teams describe the work that needs to happen (sales, marketing, operations, finance) and agents do it, reaching out via WhatsApp, SMS, iMessage, or voice when something needs a human call. We run it ourselves in production. A team of seven operating at the output of a company three times our size.

We announced CAD $4.3M USD in seed funding this week from Frontline Ventures and iNovia Capital. The founding team has previously built and sold companies to Workday, MessageBird, and Fox.

The role is for a senior AI engineer who has restructured how they work around AI. Claude Code as primary development environment, production agent systems with real scars from it, and strong opinions about what works versus what demos well. The work covers agent reliability, session infrastructure, secure VM environments, and the AI-native development practices we use to build the product itself.

Open article: Senior Full-stack AI Engineer - Toyo AI by apply.workable.com

What 'makes' the AI data stack? How do you architect it well? When do you start using Snowflake vs. DuckDB?

Here's what hit for me at tonight's Vancouver Agentics Foundation Meetup (thanks Robert Ranson and Bill McGraw for hosting):

3 things that'll save backend and AI engineers hours of bad architecture decisions:

1. DuckDB vs Snowflake isn't about preference, it's about thresholds. 

Stay local-first until your pipelines regularly exceed 20-30 minutes, modeled data crosses 50-100GB, or you hit 3+ concurrent contributors. Before that? 

Snowflake is just wasted resources.

2. Business logic belongs in dbt models, not orchestration code. Dagster owns the run order. dbt owns the logic. Mixing them is how "temporary" models become production dependencies nobody can touch.

3. The real "modern" in modern data stack isn't the tools. It's the operating model: code-defined pipelines, automated validation before consumption, and modular components you can swap as scale changes.

We built a game to make this stick: https://lnkd.in/g3vgh6XJ

6 zones. 18 lessons. 15 questions. If you're onboarding data engineers or just want to test yourself, try it.

#ai #dataengineering #analyticsengineering #snowflake #duckdb #dbt  #aiengineering #yvr #aijobs #fde

Nobody is teaching senior developers how to think about the modern ai data stack.

There are docs. There are tutorials. There are courses.

None of them answer the question that actually matters:

Why does this layer exist, and what breaks when you blur the boundaries?

So we built a game at DASS Services NA that does.

It covers the decisions teams get wrong before they open a terminal:

When to upgrade from DuckDB to Snowflake. What order to build a pipeline. 

Where logic belongs and where it doesn't.

Play it here: https://lnkd.in/g3vgh6XJ

#aijobs #aiengineering #vc #fullstack #yvr #singapore #london #switzerland #ai #aws

I love building high performing teams and cultures. 

I am a go-to-market executive with 15+ years of experience in helping technology companies grow rapidly through data-driven marketing. Most my experience is in B2B SaaS, but I have worked with startups and scaleups in Ecommerce, Mobile, SMB, Enterprise, and Non-Profits ranging from $0-$400M+ in annual revenue.

As VP of Growth Marketing at Clio, I lead our global growth team across Canada, the United States, Ireland, UK, and Australia. In my role, I partner with the rest of Clio's executive team to accelerate Clio’s industry-leading customer acquisition strategy.

I am also a frequent speaker primarily on topics related to marketing, startups, and legal tech. If you are interested in having me speak at your next event or on your podcast, please send me a message.

Alex Shipillo

Over the last few weeks, my timeline has been filled with commentary and articles on the "Death of SaaS". Technology is changing so fast, but what gets me excited is that this new wave of disruption will enable a small handful of companies to truly accelerate their growth and impact through AI. 

Clio is one of those companies. The legal industry that we serve is going through a massive transformation, and Clio has all the scale, resources, and trust to help legal professionals figure out AI. Our product team has been innovating at an incredible pace and delivering massive value to customers.

I'm looking for a new key leadership role on my team - Director of Demand Generation - to tell this story to the legal market and help us bring more law firms into the Clio ecosystem. This is a role with a lot of resources, a lot of visibility, and a lot of impact. You'll lead a high performing SMB-focused Demand Gen team that drives meaningful scale ($X00Ms of Revenue).

I'm open to hiring the right candidate anywhere in Canada/US. Thanks in advance for sharing this posting and sending your referrals.

I'm looking forward to joining the Clio team in Chicago next week for ABA TECHSHOW. If you're going to be there and would like to meet up in-person or would like to be added to the guest list for Clio's Thursday night party, please drop me a message!

Toronto legal friends! Join me and Luke Slan on March 31st as we celebrate the new chapter of Clio in Canada! Hope to see you there.

🇨🇦  GTA legal community- Clio is bringing Draft on tap to Toronto!

Join us March 31st at the Walrus Pub to celebrate the next chapter of Clio in Canada.

With the launch of AI-powered document drafting, we’re marking a major evolution in how our platform serves Canadian legal professionals. Beyond Clio Draft, I’m looking forward to hearing Clio CEO and Founder Jack Newton share our vision for where the Canadian legal industry is headed and how we are evolving the platform to get there.

Come to catch up with GTA peers, connect with Jack and our leadership team, and be a part of what’s next for the Canadian legal industry.

The Details:
Walrus Pub & Beer Hall (Lower Level)
Tuesday, March 31 | 5:00 p.m. – 7:30 p.m.
Draft beer, drinks and appetizers are on us!

RSVP to save your spot:

https://lnkd.in/gWFdMWaS

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The Battle

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