About
Before founding CashIO, Alex spent seven years in B2B software, leading product marketing…
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Alex Ruddock reposted thisAlex Ruddock reposted thisI’ve got a new TikTok song stuck in my head. But this one? This one hits different.👇 We just launched a first-of-its-kind campaign for Make-A-Wish® Canada, led by the creative force that is Zulu Alpha Kilo. Make-A-Wish’s platform is built on a powerful truth: wishes are literal medicine. Yes, a wish can measurably improve outcomes and resilience for children facing illness. Zulu uncovered something else that can support healing in kids: music. So what if we brought those two medicines together and partnered with one of Canada’s most loved TikTok music Creators to create an original, platform-first song? And what if every time the track is used on TikTok, proceeds go toward granting wishes for children with critical illnesses across Canada? Proud to say Wish Song launches today! Check out the music video and full track here (alert: it’s an earworm): https://lnkd.in/gPFJH5EC Or, if you’re feeling creative, give the karaoke-style Branded Effect a try: https://lnkd.in/gyEAQu4v Massive thank you to the team behind this remarkable charitable effort!👇 Sean Bell Sarah Yim Jaya Rizzi Elyssa Seidman Jenny Glover Jordan Alperin Guilherme Maximiliano Oss Rech Jesse Brook Deana Shaw Steve Kulach Alan Kachar Jeff Topol Jeff Stempeck Nik Djukic Walker Joshua Bloom (He/Him) Joe Mendrala Milica Kovacevic Daniel Klug Kinney Edwards TIKTAL
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Alex Ruddock posted thisBotkeeper’s Shutdown Is a Tough Moment for the Industry. After more than a decade in business, Botkeeper announced it’s closing its doors. In his public note, CEO Enrico Palmerino shared that their platform could code 80%+ of transactions with ~98% accuracy, and that new products were close to launch. He also cited rapid macro shifts and industry consolidation that materially impacted revenue — particularly among larger clients. The company explored acquisition and financing options before deciding to wind down. Building in accounting tech is hard. Building for over a decade is even harder. That deserves respect. But there’s an important lesson here. If the automation was progressing, then the challenge wasn’t simply product capability. It was resilience under external pressure. We talk constantly about Product-Market Fit. We talk far less about Capital Resilience. Some considerations... 1. Client concentration If revenue is heavily weighted toward one segment, consolidation or contraction can hit hard. Diversification isn’t just about growth — it’s about durability. 2. Margin structure Runway measures time. Margins determine flexibility. High gross margins create room to adapt. Low-margin models with significant service costs leave less margin for error. 3. Ability to adjust without new capital When capital markets tighten, pivots can’t depend on the next round. Operational agility matters as much as product velocity. None of this minimizes what the team built. My takeaway: Technology improves efficiency. Financial structure determines survivability. For those building in consolidating industries, the question might be: If our top revenue segment shifted tomorrow, how prepared would we be?
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Alex Ruddock shared thisIntroduction to CashIO Part 4: Let's Talk Data! A platform like CashIO is only as good as the data we can use to derive insights. In this micro-demo, we're going to walk through QBO, Xero, and bank integrations. All of our quality checks, forecasts, and insights are generated from first-principles using this data. As always, if you have questions/recommendations, let us know!
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Alex Ruddock shared thisIntroduction to CashIO Part 3: File Quality Tracking, Alerts, and Task Management Accounting firms don’t usually struggle with effort. They struggle with visibility. As client count grows, work-in-progress gets fragmented across people, tools, and inboxes. Issues surface late. Tasks get created manually. Follow-ups slip. CashIO is trying to fix that. Our File Quality tools give you a live snapshot of every client and entity—so you can immediately see what’s clean, what’s drifting, and where quality is breaking down (missing accruals, messy transactions, stale bank or card feeds). Our Tasks try to close the loop automatically. When the system detects an issue, it creates and assigns the task. When the issue is resolved, the task closes—no manual admin required. Short demo below 👇
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Alex Ruddock shared thisIntroduction to CashIO Part 2: Workload Tracking, Pricing Insights and Employee Capacity In the world of services businesses it's helpful to know how much work a client takes, how that's trending over time, and who on your team has the capacity for more labour. We specifically help fractional CFOs and accounting firms figure this out by reading directly from all the GLs associated with a client and tracking these changes over time. If a client adds additional entities, bank accounts, a new currency, etc. we can arm you with the data to go back to that client and have an informed discussion on pricing. Likewise we can track the impact of these changes on employee workload and tell you who has additional capacity. Here's a demo to give you a sense for how this works.
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Alex Ruddock shared thisAn interesting topic for any services firm. To those of you running your own, what are you trying and what are seeing?Alex Ruddock shared this😳 BREAKING: McKinsey just redefined “headcount.” 40,000 humans. 25,000 AI agents. What changed fast: ▫️ 18 months ago: a few thousand agents ▫️ Today: 25,000 agents running autonomously ▫️ Next: one agent per consultant, minimum ~40% of McKinsey’s work now flows through its AI division. ▫️ They want people who can switch between consultant and engineer ▫️ Strategy and building collapse into one role ▫️ Leverage comes from orchestration, not headcount And the business model moved with it: Hourly fees → OUTCOME guarantees If BCG has consultants coding on-site, and McKinsey has 25,000 agents in the field, The consulting wars just entered a different phase. AI Resources you might find helpful: • OpenAI’s New Playbook for Product-Market Fit in AI Startups https://lnkd.in/dy-HgVtX • 2,500+ Angel Investors Backing AI Startups - https://lnkd.in/djjN-TD2 • 50 AI Agent Startup Ideas for 2025 - https://lnkd.in/dy9E-MCn • AI Co-Pilots for Startups & VCs - https://lnkd.in/dSX3ss2q • The Agentic Revolution - https://lnkd.in/dadFm25a • 118 AI Communication Agent Use Cases - https://lnkd.in/dr9cM5BT
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Alex Ruddock shared thisAs promised... Introduction to CashIO Part 1: Client Management and User Roles for Accounting Firms These are not the flashiest features but I think it gives you a good sense for how we think about clients, entities, employees, roles and permissions.
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Alex Ruddock posted thisOk. So here’s the plan for 2026. We’re going to be debuting our features here. One at a time. The goal is simple, you tell us what you think, we ship based on your suggestions. If our capacity insights fall short tell us how and why, if our budget AI is lacking we’ll ship improvements, if our prepared for you advisory agendas aren’t helping you ask the right questions, we’ll adapt. CAS is the next step for accounting firms but they need real support, real tools, and real aids for the teams who will be doing the work. Our goal is to build that platform and make it indispensable. Stay tuned for our first batch of debuts later this week!
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Alex Ruddock shared thisAs 2025 comes to a close, I wanted to reflect on the year. It's been a big one. We've been heads down, building, attending events, attracting early pilot firms, and delivering new product updates every week. I've done a lot of hinting at the platform we're building, CashIO.ai. I promise, more details will be coming soon. In fact, January 2026 will mark a shift in how we approach talking about what we're doing. Did someone say product demos? I've been quietly getting things ramped up on here and have barely scratched the surface in terms of the kind of content we want to create and the conversations we want to have with all of you. To all the pilot users, investors, partners, and advisors who have donated their time to us this year, THANK YOU. You know who you are and we seriously appreciate it. Part of the job of being a founder is not taking "no" for an answer. I'm sure many of you can attest to that based on the messages in your LinkedIn inbox. We want your attention and your time and I'm not afraid to ask for it. But... in exchange, we promise we're taking every note, every idea, every morsel of feedback and using it to fuel what we're doing. At the end of the day, we're building for you and the only way to do that is inviting you on the bus. To my team, you are all superstars. Your level of commitment, attention to detail and frankly, speed is inspiring and gives me the energy to push even harder. To all the CAS firm owners and fractional CFOs out there, all I ask is this. Pick up the phone in 2026. I promise, you'll be very interested to learn about what we're up to. Kudos to Anderson Petergeorge, CPA for the inspiration behind this post and for being such an awesome host when we popped by the office earlier this year. Looks like I've got a long way to go on my LinkedIn numbers! Onwards and upwards!
Alex Ruddock commented on a post
1mo
🎉🎉🎉
Alex Ruddock commented on a post
1mo
The profession isn’t dying. If anything, demand is probably overtaking supply. Automation doesn’t replace judgment. It preserves judgment by removing noise.
The big question on my mind is as the basic record keeping gets easier what do bookkeepers do with the time savings?
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Alex Ruddock liked thisAlex Ruddock liked thisSomewhere out there a CPA wants to quit today. Reconsider. The industry needs you. You just might need a change in scenery.
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Alex Ruddock liked thisAlex Ruddock liked thisS-Corps get marketed as tax-saving tools, but tax basis is what actually matters. It’s tracked on Form 7203 and determines whether your distributions are tax-free. If basis stays positive, you’re fine. If it goes negative, the excess becomes taxable at the shareholder level. This usually happens when the company has losses and distributions are still being taken. Debt can help with losses, but it doesn’t protect distributions. Track your basis before taking money out.
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Alex Ruddock liked thisAs nonprofits grow, governance and financial oversight must evolve just as quickly. Here is a piece I wrote on what boards should watch for as growth and scale introduces new complexity and risk considerations.Alex Ruddock liked thisKevin Costello, CPA is seeing a common pattern across growing nonprofits. Growth is starting to outpace systems. As funding expands, boards and leadership teams should be asking: • Do our financial systems provide clear visibility into program performance and cash flow? • Is staffing and financial oversight keeping pace with the size of the organization? • Do we have sufficient operating reserves if funding timing changes or expenses increase? • Are we investing in systems and processes that will support the next stage of growth? Organizations that address these questions early tend to scale more smoothly. Those who wait often find themselves upgrading systems and processes while already under strain. If any of these questions are difficult to answer for your #nonprofit, this is worth your time. 👉 Discover the signs growth is outpacing your systems, read relevant insights, and more from LGA's Kevin Costello: https://lnkd.in/exxWyV_S
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Alex Ruddock liked thisAlex Ruddock liked thisThe brain🧠. Arguably the most intricate and complex organ in the human body. It controls how we think, feel, move, and experience the world around us. Every memory, every emotion, every action begins in the brain. Yet brain diseases, including brain cancer, remain among the most challenging conditions to understand and treat. A challenge compounded by insufficient research funding. During Brain Awareness Week, we recognize the importance of advancing brain research that helps scientists better understand this remarkable organ. At Brain Cancer Canada, we are proud to support brilliant researchers across the country who are working to unlock the brain’s mysteries and develop better treatments for brain cancer, because, when we invest in #research, we invest in hope, possibility, and the future of every patient and family affected. #BrainAwarenessWeek #BrainResearch #BrainTumour #BrainCancer
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Alex Ruddock liked thisAlex Ruddock liked thisYour separate business account won't save you when the IRS audits your books. Opening a separate account is step 1. Many business owners stop there. That's where the problem starts. Here's what mixed finances actually look like: → Personal expenses paid from the business account → Business expenses paid from personal cards → Random owner draws with no structure → No clear link between payments and purpose On paper, your books look messy. And in an audit, every deduction gets questioned. This is what real separation looks like: 1. Every business expense runs through the business account or business card 2. Your entity structure dictates how you pay yourself. Pay yourself on a set schedule (through payroll or owner’s draw/distribution) 3. If you use a personal card for business, the business reimburses you, and you keep proof 4. Capital you put in the business is recorded as owner contribution, not as business revenue 5. Personal loans and credit cards stay personal; business loans and cards stay in the business A separate account is just the container. What you run through it and how you document it are what actually separate you. Are your finances truly separate or just "separate enough"?
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Alex Ruddock liked thisSo true :)Alex Ruddock liked this“If people would just do their f***ing job, we wouldn’t need software like this.” A guy said that to me at the end of a SiteStack demo today. $500M+ construction company. Runs a major region. Knows his stuff. And I laughed—because every executive has thought this at some point. But here’s the problem… 👉 You’re assuming the job is actually doable. Let’s break down what we ask teams to “just do”: - Track equipment across hundreds of jobsites. - Pick the best supplier based on price, distance, and availability (not just who they know). - Manage deliveries, pickups, extensions, and call-offs. - Reconcile invoices that don’t match POs. Do all of it across emails, texts, calls, and spreadsheets. And then we say: “Why isn’t everyone just doing their job?” That’s not a people problem. That’s a system failure disguised as a performance issue. When there’s: - No visibility - No standard workflow - No system of record - People don’t manage the work…They survive it. So they: - Default to the easiest vendor - Miss things - Let costs leak - React instead of control Not because they’re bad—but because we’ve made the job impossible to do well. That’s on us as leaders. Our job isn’t to demand better execution from broken systems. It’s to fix the system. That’s what we built SiteStack to do: - Show you the right supplier for every job - Automate the workflows that fall through the cracks - Catch the billing mistakes no one has time to chase In other words… 👉 It doesn’t replace people doing their job 👉 It finally gives them a way to actually do it And when that happens…It’s amazing how quickly “people not doing their job” disappears.
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Alex Ruddock liked thisAlex Ruddock liked thisThis coming Tuesday, catch me speaking at the 5th Annual Leadership & Civility Conference being headlined by Johnny C. Taylor, Jr., SHRM-SCP, President & CEO of SHRM. Clarity is a leadership deliverable. Not a value, not an aspiration — something you produce. Talking about what actually looks like in my practice. Still time to grab a ticket! williambhenry.com
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Alex Ruddock liked thisStrong financial planning from day one can be the difference between surviving and scaling. Get in touch now: https://lnkd.in/dJTqR-_SAlex Ruddock liked thisDid you know nearly 1 in 5 small businesses don’t survive their first year? That’s why having the right financial strategy from day one is critical. At AccounTax Bookkeepers, we focus on helping business owners stay ahead with proactive planning, clear financial visibility, and expert support—so you’re not just managing numbers, you’re making smarter decisions. If you’re starting out, putting strong accounting systems in place early can make all the difference in building a sustainable and successful business. Learn more about how to set your business up for success in its first year here: https://lnkd.in/dupbfh3m #SmallBusiness #StartupSuccess #FinancialPlanning #BusinessManagement #Entrepreneurship #Bookkeeping #FinancialManagement #Accounting
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Alex Ruddock liked thisThis is a great quick read explaining how nonprofit leaders can implement proactive Federal Form 990 compliance, as well as how to remedy potential noncompliance issues. See below! 👇Alex Ruddock liked thisOne of the most common and costly compliance issues nonprofits face? Failing to file required annual tax returns, typically IRS Form 990 or its related filings. Missed filings are often unintentional, but the consequences can escalate quickly. An organization’s tax-exempt status, funding, and reputation can all be put at risk. The good news is that with the right awareness and a proactive approach, this is preventable. Nonprofit leaders can take steps to stay compliant and avoid unnecessary risk. 👉 Learn why it matters, the consequences of not filing, and how to stay ahead: https://lnkd.in/epbVRMAg
Experience & Education
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CashIO.ai
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Standard First Aid
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English
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National Lifesaving Society
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