Jeff Roy

@WorkflowWhisper Playbook

I built 31 automations for clients last year. Every single business - from solo founders to 50-person teams - needed some version of the same workflows. So I documented all of them. Every workflow. Every department. And the exact plain-English prompt that builds each one in minutes. Sales & CRM: lead capture, follow-up sequences, deal tracking, proposal generation, pipeline alerts Marketing: social scheduling, email sequences, content repurposing, UTM tracking, review requests Operations: invoice generation, payment reminders, inventory alerts, automated reporting Customer Success: onboarding emails, NPS surveys, churn detection, support routing Admin: meeting scheduling, expense tracking, document generation, approval workflows Each one includes the specific prompt I use to build it - not vague instructions, the actual sentence I type. Plus which 3 to start with if you want to save 10+ hours/week immediately. Comment "PLAYBOOK" and I'll DM you the full PDF for free.

@Shahriar661731 Claude

SHOCKING: 99% people using Claude are barely scratching the surface. Right now, the entire internet is screaming “Claude, Claude, Claude”... But here’s the truth: just chatting with it won’t change your life. To unlock its real power, you need to master: • agentic workflows • Claude Code • skills, automation & system-level usage I spent 100+ hours researching and compiled the best Claude resources from across the entire internet — videos, repos, guides, books, and papers. I’ll give it to only 4,500 people. To get it: 1. Follow me MUST (so i can dm) 2. Comment “Claude” 3. I’ll DM you the document 📩 If you don’t follow or comment, you won’t receive it

AI Darwinism: The survival-of-the-most-adaptive era of business, when intelligence accelerates the pace of change that advantage shifts from size and speed to learning velocity and reinvention. It rewards those that evolve their operating model by combining human judgment and creativity with machine agency, redesigning work to move faster in learning and execution. #adaptordie

The shot clock person at @TorontoRockLax is so off. @BuffaloBandits shoot on own net and they put four shots up. Missed about 8 shots on @TorontoRockLax They obviously never played net and do not understand save percentage.

Great opportunity @101WestonLabs for agentic agent work.

Playbook

Thoughts on Team Canada at World Juniors: There's been a lot of discourse today about Canada's performance after bowing out to Czechia again. I've read a lot about roster construction, team toughness, how players were used during the tournament, and other things related to the team's inability to get the job done. These things may have been an issue, but reality is the problem runs way deeper. Here is the biggest thing that people aren't talking about: Canada has WAY fewer youth boys playing hockey than it did a decade ago. Looking at Hockey Canada registration and membership data, it's mind-boggling to see the numbers. And the numbers in the biggest provinces (Ontario and Quebec) are especially egregious. So why is this happening? Hockey is Canada's sport. It shouldn't be like this. It's what we hear every day from families all over North America: Costs are too high. It's professionalized at too young of an age. The stress of the youth hockey experience is too much for kids and families. Community programs have been replaced by for-profit entities leading to higher costs and more pressure. Development has been replaced by super teams and rogue/outlaw leagues outside of Hockey Canada even before kids are 8 years old. At the older ages, hockey academies have become what families believe is the only way their kids will make it - shelling out INSANE amounts of money to send their kids to do so. Ontario just got rid of residency rules which will only lead to less accountability and more club-hopping than there already was in the nation's craziest and biggest youth hockey market. The reason why Canada was the hockey superpower for so long is because it was part of the fabric of the country. There was such a pride and passion for the game and what the game meant to the flag. There was such a sense of playing the game for something bigger than yourself. Now rather than playing for the love of the game, hockey in Canada is like a job for many of these kids in the environment they're being put in. It's less about pride and passion and more about the path to making it. When in all honesty, it's the pride and passion for the game that is the biggest consistency in the kids that do end up making it. If Canada wants to restore its hockey dominance, it better take a long look in the mirror at the grassroots and what is going on in youth hockey. If you have tens of thousands of fewer boys playing the game, you should probably look at that first. The bigger your pool of athletes, the more elite athletes you can develop. "As many as possible, for as long as possible, in the best environment possible". That has to be the guiding principle. There's a lot of great people in Canada doing incredible things for the game, but the system itself is fundamentally broken. If Hockey Canada is serious about getting back to the top, it has to start at the bottom.

23% report their organizations are scaling an agentic AI system(expanding the deployment and adoption of the technology within a least one business function), and an additional 39% say they have begun experimenting with AI agents. Most are scaling agents in 1 or 2 functions. In any given business function, no more than 10% say their organizations are scaling AI agents.

Paul Fletchers from @AvivaCanada nails it about the issue of knowledge transfer in the insurance industry. “It takes seven years to become a brain surgeon but ten years to be considered a senior underwriter. 🎤 drop Need to use AI , learning management systems , prompt engineering to get u/w up to speed faster. #ibaocon2025 @IBAOntario

Great to see all the hard work the industry is doing at CSIO is making a difference. I have been honoured to work with CSIO for last six years through my involvement with @IBACanada And serving on the @CSIO #innotech and #governance subcommittees. Great to see brokers , companies and BMS vendors working to improve connectivity.

@OurLeafsNation Leafs 1–13 in clinching games Ottawa 0-7 when down 3-1 in a series WHO wins this series ? Who is going to improve some nasty stats. Disappointing game for Leaf fans. #LeafsForever #leafnation

The #Leafs still control this series! Take a breath #LeafsNation It’s just going to take a game or 2 more than we had hoped! #LeafsForever    #LeafsNation #Leafs #BringThePassion #StanleyCupPlayoffs

It is not the heat its the humidity. Its not the cliche by the person saying it. Not the company account executive it is the lack of hiring and training they did not get from their insurance company to track real data and have suggestions or ideas how to improve things. This rep is checking a box to get a bonus and covering their behind with results (looking after themselves) When you asked the company AE ? what ideas they had for retention when they cancelled all your accounts what ideas did they have ? What was your retention rate they figured out for you this year given the list of accounts they knew they where cancelling. A good rep would have had this ready and looked at your retention after this was factored in vs looking at traditional numbers. This US Carrier needs to do a better job.

When a carrier has the audacity to tell you that you need to work on your retention with them when they non renewed half your book and the other half got 100% rate increases….. Ok Mr. Carrier, our agency runs about 96% retention…. Sounds like a YOU problem.

Curiosity revenue = be careful your product does not becomes someone else’s feature . Lot of one idea or one hit wonders . We are in a big country of hype to use and 80’s one hit wonder band reference . Brokers and agents do not need any siloed solutions or one hit wonders that do not talk to each other . Need APi integration. Some cool AI companies trying to provide integration or data orchestration . We will see how they make out

Fine, I'll say the thing that no-one is saying... There's a bunch of AI companies with $1-10M "ARR" raising big VC money on what I'll call "curiosity revenue" - not real sustainable ARR. Basically, what's happening right now is a lot of people have high willingness to try AI products. They'll sign up for a free trial, maybe even convert to paid for a couple months out of curiosity. This creates a temporary revenue spike that looks like product-market fit but isn't. They call it ARR, but it's more like "hey I'll try this product revenue". Of course there are companies like Replit, Cursor or Bolt that are building real products solving actual workflow problems. These companies have genuine retention and expanding usage. And hey, companies like Bolt had been building for like 6 years prior to adding any AI features. Replit has a similar story I think. But many AI startups are riding a wave of novelty and FOMO, not solving real problems. They're showing investors nice growth curves that will flatten in 6-12 months when customers realize the product isn't actually improving their work. A slick demo reel + stripe payment +novel feature might be good enough to try but may not be enough to be a true ARR type of customer. And then we will see a bunch of zombie AI companies. The people who will get hurt will be the employees who think their stock is worth millions but then the founders go and try to raise more money but try raising money when revenue is down 65%. The real tell is retention. Are people still using the product 6 months in? Are they using it more over time? Or did they try it a few times, got the "wow" moment, and then slowly stopped? By the way, even companies with true PMF are at risk. The AI landscape shifts so rapidly that your PMF can be temporary. Example: we're seeing people switch from ChatGPT Pro at $200/month to Grok/Perplexity Deep Research for free with barely a second thought. Unlike previous tech cycles (mobile, web), where advantages could last years, AI competitive moats are filling in weekly. We're probably 18 months away before we start seeing a bunch of zombie companies. The AI companies that survive will be the ones that focused on solving real problems, iterating as the market changes, building true community and not just demo-ing cool sizzle reel after sizzle reel. Am I wrong?

The "8 hours of sleep" rule is based on ZERO evidence. Ancient humans slept in two distinct phases, not one long stretch. Here's the shocking truth about how you should really be sleeping:

Super honoured to do our first Digital Insurance Pint Podcast live in front of 200 awesome brokers at RCCAQ innovation at #sommetech2025 in Montreal. Our team of Tom Reid Adam Mitchell Steve Earle and myself explored the following items on this episode. Transformative role of AI in enhancing brokerage operations and customer experience in a rapidly changing world. We discussed the importance of leveraging data as a competitive advantage highlighting the need for brokers to clean and utilize both structured and unstructured data. We shared AI tools we are using and we gave Steve Earle a brief therapy session on AI technology over whelm and much much more. Think big , start small , learn fast Steve. Super cool the RRCAQ team had beers for our session to make it 100 percent authentic. I am a big fan of how the Quebec brokers are coming together to build technology together. Love the work the team at RCCAQ innovation is doing to help brokers adapt to a changing world. With AI we do not have 20 years like we did to digitize our business we have 20 minutes. As I stated the key formula to future proof brokerages is AI + humans = superbrokers. (Augmentation) Always great to have dinner with our good friend @SherifGemayel from Trufla and reminisce on our journey together and how we are working to change our industry. Great to see so many great industry people and vendors. Merci aux courtiers du RCCAQ. @regroupment des cabinets de courtage d’asurance du Quebec . #DigitalInsurance #Insurtech #Brokerage #AI #Innovation #PodcastInsights

Your action plan: 1. Build for the AI-first world 2. Learn AI infrastructure fundamentals 3. Focus on industry-specific problems 4. Learn skills that can't be replaced or automated The next decade of wealth creation starts now.

There is a new crop of insurtech that realize they do not understand the agent broker landscape and they want to work with Agents. The smart ones join @101WestonLabs and work with agent advisor and get real insight. They learn how their product can solve a problem in the agent world and how to develop unique selling propositions. They let agents become angel investors and thus helps connect their products with other key agents who make it better. It is Waze vs garmen GPS approach. More users and feed back helps the product morph. Technology and AI needs to done with agents not too agents. I know five or ten key agents that either advise and or invest and the startups that are smart enough to have and agent in the loop from the ground flower win. The key with insurtech is they must replace a task or jobs at cheaper price point. Their product must improve productivity , efficiency , have an ROI , make things easier and better for clients. Taking your personal lines buying experience is not going to cut it. The future is Agent + AI = super agent. How can the insurtech help fill the missing middle which is how we connect the two together ? @bradleyflowers @ParadisoPresent

The problem with ai inspired tech entrepreneurs that try and come into insurance is largely their view and experience of the industry is limited to being a consumer of personal lines insurance. Far greater and much more nuanced problems that ai can actually solve live in the other 90% of the industry that they have never seen. Then you have those that understand this to a point but aren’t “in it” and you get start ups that are solving made up problems that don’t exist.

Agent-driven tech solutions? Sounds like music to our ears. Read more from @IIABA on how this approach is changing the #InsurTech landscape at iamagazine.com/magazine/issue… #Insurance

We had a great meeting with @jroy5 from @ExcaliburGroup as part of our latest merger! It is awesome to have a group like Excalibur join #TeamMcDougall especially when they hook you up with their custom jerseys! Looking good team!