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Harry Roy McLaughlin

🤖 Adopting AI |💰 Capital Raising | 👨‍👩‍👧‍👦 Building Teams | 💣 Avoiding Landmines

Winnipeg, Canada (-06:00 UTC) Englishfrom Winnipeg, Canada
Usually responds in 1 day
$200 / hour
Price per hour
30 min
Time Blocks Available
4.99
100 reviews / 130 sessions
Tue
13
Next availability

Harry is an absolute legend. He has real world CURRENT knowledge of the fundraising process. It doesn't get any more tactical than this. He provided me with resources, funnel metrics, and other specific insights you wouldn't even imagine unless you actually met Harry. Extremely helpful on my fundraising journey. And he has an awesome personality to boot. Very happy I booked a call with Harry.

Peter Antonov

Hey look, most of the sessions I had here were good, and I've learned A LOT! And every now and then you come across a session with a speaker that's very very good! And that happened with Harry, absolutely amazing session, with lots of learnings compressed in a 30 minutes call! I'm going to book at least couple of sessions with Harry!

Mihai Sava

The session with Harry was THE most productive session I have had in Growthmentor. Harry's inputs and the materials he shared were gold. The "Insider" tips that he guided me with was practical and implementable immediately. Not only did he pack so much information in a session, he was extremely attentive and patient. I am hoping that I can bother him again for another session soon.

Ajith S

Bio

After a successful and exciting run in the Wealth Management industry, I started my own Fintech Startup. I then moved to Toronto to grow a Startup from 6 employees to over 60, leading financing rounds that raised millions of dollars (14+) and leading numerous large partnership deals with some of the largest insurance companies in the world along the way. Recently I have been helping companies generate explosive growth through innovative digital marketing strategies (Growth Marketing/Hacking), executing partnership strategies, optimizing funnels, and implementing data-driven growth strategies. Currently, I work on/with the C-Suite of large enterprises in Growth and AI Adoption strategies. I am highly passionate about giving back to the Startup Community that has been so good to me over the years, so multiple times a week I advise / mentor startups, their founders, and their executive teams, on all the issues an entrepreneur or startup will face as they progress through their stages of growth. I do this for free as it is truly rewarding to both parties.

Expertise

  • Advice on funding

    I have helped raise tens of millions for startups in the past. It is a specialty of mine and I love helping out whenever I can. You can see my personal investor database (with emails, LinkedIn URLs and more, at www.2i.vc)

  • Bootstrapping

    The value of bootstrapping is often not understood and not properly valued. This seems to be changing though, which is a good thing. Nothing beats building a business from zero to something.

  • Conversion rate optimisation

    This is one of my favorite things to do in the world. I just love the challenge of figuring out how to drop conversion rates and increase funnel optimization. I get a rush from every penny saved, every step removed, every metric improved.

  • Copywriting

    I founded an AI Copywriter as a side gig. Probably enough said there. . .

  • Data science

    When Excel's 1,048,576 rows isn't nearly big enough, you are probably working on some data science project. Time to fire up R. . .

  • Growth marketing

    The subtle art of pushing the envelope of experimentation and marketing. . .

  • Idea validation

    Problem Interview, Problem Interview, Problem Interview, Problem Interview, Problem Interview, Problem Interview, Problem Interview, Problem Interview, Problem Interview. It sucks, I know, but it has to be done, it has to be data-driven, and it should never end.

  • No-code

    IT IS THE FUTURE!!! I learned Bubble in a weekend and could confidently build almost anything to an MVP stage within a few days. I can't imagine what a team of No Code guru's could accomplish working together like as a well-oiled dev team. It needs to be in the toolkit of every startup or growth focused team.

  • Product market fit

    Far too many times have I seen companies burn far too much money without ever proving out product-market fit. Sadly it can usually be done without spending much (if any) money.

  • Remote work

    Remote work is not the same as in the office, so you have to work very hard to make sure remote teams are as effective as face-to-face teams. Most managers were never trained for this, and it is certainly a perspective shift. How do you build the same rapport? How do you keep staff accountable? How do you keep them motivated? The shift to remote work opens up amazing opportunities, but it also opens up many risks that need to be expertly navigated.

  • Sales

    Sales needs to be data-driven, and far too often it is not. The good thing about sales teams is that they are good at selling products. The bad things about sales teams are that they are also good at selling their results to management (especially if bad). Setting up indisputable KPIs, tracking metrics that matter, and creating a culture of motivated sales growth is so important to early-stage companies.

Toolkit

  • Adobe Analytics logo

    Adobe Analytics

    Using Adobe Analytics, I gain valuable insights for projects & side gigs by tracking user behavior, identifying trends, and optimizing conversion rates. This data-driven approach ensures that I continue making data-driven decisions.

  • Ahrefs logo

    Ahrefs

    I started using Ahrefs in 2016 when I was working on SEO for a Fintech company, and I could hardly live without it now. The insight you can draw from it are amazing.

  • Amplitude logo

    Amplitude

    There is almost nothing more important than having good data when it comes to growth, and Amplitude is essential in tracking key metrics in your app/websites/funnels.

  • ClickFunnels logo

    ClickFunnels

    You can learn a ton about landing page optimization just by looking at ClickFunnels landing pages. Russell Brunson (CEO) is also someone to watch. He know's his stuff and you can learn a ton from watching his youtube videos.

  • Meta Ads logo

    Meta Ads

    To date, FB is (sadly) still one of the most effective ad platforms. That being said I have been having great success on Snap and TikTok recently. I have helped spend many hundreds of thousands of dollars on FB and know it better than most.

  • Google Analytics logo

    Google Analytics

    Of course you need to know Google Analytics if you care about your website, your funnels, you market... Needs to be in everyones toolkit.

  • Hotjar logo

    Hotjar

    Screen records can give you insights that you normally would miss. I have wasted so many hours trying to debug a funnel, and then simply checked the screen records and found my answer within seconds. Record all funnels is the lesson here.

  • HubSpot logo

    HubSpot

    HubSpot’s CRM platform has all the tools and integrations you need for marketing, sales, content management, and customer service. Each product in the platform is powerful alone, but the real magic happens when you use them together.

  • Intercom logo

    Intercom

    Used to use this on some of our test brands. I know it well, but not the biggest fan. . . .

  • Jira logo

    Jira

    A must for any dev team. Employing Jira, I can effectively manage projects & side projects by organizing tasks, tracking progress, and collaborating with my various teams. It helps me streamline workflows, ensuring timely delivery and success. Love it.

  • Mailchimp logo

    Mailchimp

    I've used Mailchimp for a number of brands and startups — from a small fintech startup, to a 1.4 million person mailing list, getting in the weeds and setting up the automation funnel has huge payoffs, and MailChimp is a great platform for that

  • ManyChat logo

    ManyChat

    I have scaled many a chatbot ads using Manychat. . .

  • Mixpanel logo

    Mixpanel

    I have used Mixpanel extensively and am a huge fan. Nothing beats it on flexibility and ease of use, and I have used it to its most success in optimizing conversion funnels.

  • Pipedrive logo

    Pipedrive

    My go-to CRM when the budget is tight and you just need something that integrates well with your tech stack. Easy to use/automate with Zapeir or Integromat, and wont break the bank.

  • Trello logo

    Trello

    So important to track what people are doing, especially for remote teams. Trello can certainly help with that.. . .

  • Zapier logo

    Zapier

    So so so useful for so many things. Would be hard to run a company (or a growth team) without it.. . .

  • Zoho logo

    Zoho

    I always just thought Zoho was just a CRM, but boy was I wrong. It is a beast that does everything most businesses would need (payroll, sales tracking, screen records, analytics, reporting...). Sadly it is never best in class at anything it does, but it is nice to have it all in one place.

Industries

  • SaaS

    I currently work at a B2B SaaS Fintech company in the Auto industry, and I also have a side gig that is building a AI copywriting SaaS company that I am about to scale up. I am intimately familiar with SaaS forecasting, pitching and SaaS sales enablement tech.

  • FinTech

    Grew a team from just the 6 of us to over 60 in just a few years, while raising about 14 million along the way. I know the ecosystem extremely well.

  • Artificial Intelligence

    I founded CopyBee.ai, a pay-as-you-go AI Copywriter that uses ChatGPT and other language models to write everything from Facebook ads to long-form content like Blogs and Sales Scripts as well as generates the images. Check it out at www.copybee.ai I also consult large enterprises on AI Adoption. See more about that at: www.harry.vc

  • Marketing Automation

    From Polltivia, to Optimity to Planswell, to Autocorp to CopyBee. All these companies have elements of MarTech, and all of which I had a core role in building / developing.

  • B2C

    Planswell, Optimity and CopyBee are all B2B companies. I definitely learned the most on the Fintech side though and probably where I learned the most about B2B growth.

  • B2B

    A totally different beast to B2C, B2B often takes a wildly different approach to growth. Typically needs to be much more personal, many more contact points and much longer sales cycles.

  • Politics

    Political Tech - Created a platform for Politicians to micro-target potential voters with hyper-personalized ads speaking to their exact personal beliefs and political views, empowering political campaigns to create ads custom-built on an individual voter level.

  • Machine Learning

    Currently scaling a company that uses ML and AI to generate long-form content with a simple voice or text command. .

  • Legal Tech

    Created and sold a platform to auto-generate a person's entire Will for them using either voice or text commands. This empowers people to create their own Legal Will, have it signed by executors, and updated as needed, all digitally, and legally.

Experience

  • MAAIP - Manitoba Association of AI Professionals

    Founder and Chairman of the Board

    Roy is the Founder and Chairman of the Board of the Manitoba Association of AI Professionals (MAAIP), a non-profit, member-driven organization dedicated to advancing Manitoba’s position in the global AI economy. Under his leadership, MAAIP serves as a central convening force for data scientists, engineers, entrepreneurs, educators, and enterprise leaders, aligning the province’s technical talent with private sector needs and public sector priorities. MAAIP actively collaborates with industry partners, academic institutions, and all levels of government to shape responsible AI policy, inform regulatory discussions, and catalyze investment into Manitoba’s AI ecosystem. MAAIP’s mandate spans community building, education, and ethics. Under his guidance, the organization develops programs that upskill professionals, creates forums for best-practice sharing, and promotes ethical frameworks for AI development and deployment. In doing so, it supports the creation of high-quality jobs, fosters cutting-edge research and commercialization, and positions Manitoba as a leader in trustworthy, human-centered AI.

  • Harry.vc

    Founder
    •harry.vc

    AI Consulting for enterprises looking to move to the next level. Over the years I have refined my deep-rooted passion for Artificial Intelligence, and now, every day I'm thrilled to bring my diverse experience to forward-thinking enterprises that are excited to innovate and transform in this new era of AI. My mission is crystal clear: I assist executives from leading corporations as they navigate the rapidly evolving AI landscape, ensuring they not only keep up, but strategically capitalize on AI implementation to catapult their businesses into the future. Working in close partnership with CEOs and C-Suite executives, I create comprehensive AI adoption strategies aimed at optimizing every aspect of a company's operations. My involvement extends beyond mere strategizing; I own the responsibility of executing these strategies, personally building out MVPs, proving out value, then working with development teams on scaling high-conviction AI solutions into robust, enterprise-ready solutions.

  • CopyBee.ai

    Founder
    •copybee.ai

    Create high-converting ad copy, product descriptions, marketing copy, blog posts, emails, and more in seconds. CopyBee.ai uses autoregressive language models and deep learning to create high-converting ads and supporting material by simply giving it a few keywords about your business, product, or service.

    Artificial IntelligenceMarTech

  • Polltivia

    Founder

    Polltivia, a platform built to arm political campaigns with the ability to rapidly generate databases of voters and their political views, for any given geography, and then micro-target them individually with the custom messaging that the data sais will speak to them most.

    MarTech

  • IntouchCX

    Senior Vice President - AI Strategy
    •intouchcx.com

    Crafting our AI vision, fostering a culture of innovation and continuous learning, and ensuring seamless integration of AI into our various departments and our 24,000+ employees. Leveraging cutting-edge AI solutions to drive growth, efficiency, and transform our customer experiences, all while maintaining the highest standards of ethical and legal compliance in AI implementation.

    Artificial Intelligence

  • Autocorp

    VP Growth
    •autocorp.ai

    Autocorp.ai is revolutionizing the auto finance industry. We're a fintech company focusing on ground-breaking automotive solutions that's transforming the way online vehicle shoppers interact with credit and finance. Autocorp.ai provides dealer solutions to boost volume and profitability by offering a range of digital retailing technologies mostly centered on Fintech. Our executive team consists of not just developers and marketers, but also automotive specialists who appreciate the consumer desire for seamless near-instantaneous transactions and have joined forces to deploy digital solutions into a retail setting to tackle real-world problems.

    SaaSB2B

  • Optimity

    VP Growth
    •myoptimity.com/

    Decreased the digital acquisition costs by over 90% by setting up growth channels correctly for proper targeting/optimization and deep funnel optimization. This enabled a new B2B model to be successful and since replicated with various other major insurance companies. Orchestrated the purchase of Carrot Rewards, and then the subsequent organization, summarization, and accessibility of all the valuable assets of the company to maximize its value, enabling the rebirth and relaunch of the company. Created and launched a viral waitlist campaign that added over 500,000 Canadians to the Carrot waitlist in only 8 weeks and 1.4 million in only 5 months, perhaps the largest wait-list campaign ever executed ever in Canada. Led the development of another entirely new revenue line for Optimity based around high quality, high intent, automated lead generation and sales to Financial Advisors and Insurance Agents.

    B2BHealthTech

  • Planswell

    VP Growth - VP Partnerships
    •planswell.com

    Corporate Strategy – Worked with CEO on what priorities of the company needed to be, based on the resources available to us. Executed strategic projects, which included conducting research, financial and operational analysis, structuring solutions, developing frameworks, identifying growth opportunities, preparing presentations, providing thought leadership and using hypothesis-driven approaches to solve complex problems. Business Development – Identified and pursued new strategic opportunities and distribution channels with local and international partners. International Expansion – Lead the team that established and set up partnership deals in 6 different countries. Worked on all aspects of the deals in order to overcome the huge legal and technical hurdles to needed execute. Pitching Investors – Identified many of the investors that funded Planswell and its growth. Researched and discovered potential new VCs, PE funds and individual investors, executing initial calls and pitches. Constructed the pitch decks and modeled the financials and forecasts. Actively pitched new investors selling the vision, bringing in the required team members needed to close the investment. Creating, modifying any required terms sheets and investment materials required by both parties. Establishing and executing large partnership deals - Worked the corporate ladders of the largest Insurance companies in the world to set up deals with the top executives and their teams, navigating the various corporate frameworks and hurdles in order to get deals over the finish line. Led the ‘Skunk Works’ projects - Built and rapidly tested new channels of acquisition, new business models, new product lines, new marketing approaches, as well as the acquisition of Carrot Rewards.

    FinTech

  • TRIDUS

    Founder

    Tridus, a platform to automate all of the work of financial advisors and their staff, allowing them to work entirely paperlessly and without the need of a physical office space, freeing them up to focus their time on maintaining relationships, and building new ones.

    FinTech

  • RBC

    Wealth Management Associate - Business Application Specialist
    •rbc.com

    Worked within a team that managed over 500 million in assets during the financial crisis and its subsequent recovery. Got to see the value that a strong dedicated team provides to their clients and how prudent financial planning and asset management is so important to clients and their families in the long run.

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