Chris Cicconi

"We are not sellers, but if we get a good price, we will consider it." The most expensive sentence in capital markets. Every buyer in the room just heard: we don't know what we're worth. That's not strategic flexibility, that's undefined intent and buyers will price it accordingly. There are only two coherent positions: Sellers: structure it, control the process, set the anchor. Holders: justify it with return logic, not sentiment. Everything in between belongs to the buyer. Capital strategy is binary before it becomes transactional. If the door is half open, the market will walk in before you are ready. What are you seeing in how boards handle exit positioning in the current environment? #CapitalStrategy #ExitStrategy #MergersAndAcquisitions #GCC #BoardroomStrategy #CapitalMarkets #EthikaFinanacialAdvisors

3

My focus is simple: I help Canadian organizations empower their teams with Asana. Not just implement software. But: • Align strategy to execution • Standardize workflows • Eliminate manual processes • Improve cross-functional visibility • Drive measurable productivity gains And most importantly: Help leaders scale without chaos. If you’re evaluating how to modernize operations or leverage ISVs that are actively investing in Canada, I’m happy to share what’s working across the market. Because empowerment isn’t a buzzword. It’s a competitive advantage. #Operations #Leadership #CanadianBusiness #Asana

1

Sales recruiting has its own rhythm. • High volume of candidates • Constant need to build teams at once (not just one hire) • Extra steps—test projects, background checks, benchmarking activity metrics • Staying updated with sales tools and trends It’s a department on its own, and it’s what we’ve done the most of. But we’ve also seen how other roles, finance, accounting, bookkeeping, can be equally game-changing. These aren’t customer-facing, but they bring unmatched stability and commitment. Curious about how this looks in practice? I’m happy to walk you through what these profiles bring to a team and how companies structure their hiring to make both sides work together.

6

Today our SDR teams booked 10 meetings across 7 different client accounts. Breakdown of where they came from: • 7 from LinkedIn outreach • 2 from cold calls • 1 from a contact-us form What I find interesting is this: Every few months people declare that one channel is “dead”. Cold calling is dead. Email is dead. LinkedIn is saturated. But the reality we see every day is much simpler. Channels don’t die. Poor execution does. #sales

23

Most teams don’t fail with AI because the tech doesn’t work. They fail because they try to do too much, too fast. In sales especially, trust is fragile. Processes are already stretched. The moment something feels risky or disruptive, people switch it off. What’s worked best from what I’ve seen is starting small. Pick the moments that already feel broken. Fix those first. Let the value speak for itself. That’s why we’ve always believed adoption should start where the upside is obvious and the downside is close to zero. 👇

15

Vendasta didn’t just pivot. It reinvented itself. What started as a marketplace for SaaS reselling is now an AI-powered platform that acts like a workforce for SMBs. Why? Because small businesses were drowning in missed calls, manual workflows, and fragmented tech stacks. Vendasta’s answer: AI employees that handle high-frequency tasks like booking appointments, responding to reviews, and managing follow-ups so SMBs can scale without adding headcount. The impact speaks for itself: - Molly Maid hit a 55% conversion rate with an AI receptionist - One agency doubled revenue in four months - Partners closed six-figure deals thanks to AI-driven engagement The secret? - Ecosystem activation through agencies and MSPs - Proprietary data for personalization - Modular design for scalability The takeaway: SMBs don’t need more tools. They need outcomes. Vendasta turned its platform into an operating system for growth and set a blueprint for the future of SaaS. Question for you: Do you think AI employees will become the norm for SMBs in the next 3 years? Find the full report, Vendasta’s Transformation To An AI Platform For Customer Engagement, in the comments! #AI #SaaS #DigitalTransformation #FutureOfWork

After 7+ years of building in Montreal's startup scene, I've realized it's a double-edged sword that will make or break your company. Here's what I mean: The good is REALLY good: First, there’s great talent volume. There are 4 top-tier universities, and you can hire people who came from billion-dollar companies like Lightspeed and Shopify. Outside of big hubs like SF, NYC, or Boston, it’s rare. It’s pretty phenomenal for a “small” city like Montreal to have such a density of talent. Second, the cost of living is actually fair. Your team can live comfortably without burning cash like in New York. Rent won’t crush you, and you can still find food at “ramen noodle prices.” Third, the startup community is strong. Groups that have been HUGE help for startup like us include: Real Ventures (shoutout Isaac Souweine), MTLAB, École de technologie supérieure Centech Propulsion / Acceleration programs, District 3 Innovation, FounderFuel, TandemLaunch Ventures, CEIM, Inno-centre | IC Canada, Montreal NewTech (MTL NewTech), Notman House / OSMO Foundation, Groupe 3737, Propolys - Polytechnique Montréal, Mosaic-HEC Montréal, Techstars Montréal AI, CDL-Montreal, Main Montréal, Bonjour Startup Montréal, Startupfest, La Piscine MTL, Zú, Quartier de l’Innovation (QI), Anges Québec Acceleration / Anges Québec Network, Esplanade Québec Lastly, the government subsidies are amazing. But sometimes... too amazing as I've seen some companies turn into zombie businesses, surviving on funding instead of creating real value. They're not solving problems. They're not serving customers. They're obsessed with collecting the next check. That's the double-edged sword. Government support can help you get started. In fact, it kept us at Stay22 alive. But it can also kill your hunger to build if you’re not careful. So here’s my advice to anyone building in Quebec: Use the advantages. Avoid the traps.

103

14 Comments

EXCITING NEWS: We’re kicking off the year with a SDR Leaders of Canada event in Toronto. This is not another AI hype session or sales happy hour. The focus is simple: How SDR leaders are actually using automation and AI to coach at scale without losing the human judgment that makes coaching effective. In my experience, reps don’t stall because they lack tools. They stall because coaching becomes inconsistent, reactive, or purely performance-driven. Coaching done well looks different depending on: - A vs B vs C players - Tenured reps vs new hires - Consistent underperformance vs temporary dips - 1:1s that actually change behavior, not just review numbers That’s what this session is built around. What this is not: Generic ChatGPT demos “Just record your calls and magic happens” takes Surface-level AI advice you’ve already scrolled past What this is: Real examples pulled from teams in the room How we’re applying AI across multiple SDR orgs today Where automation helps—and where it actively hurts coaching 📍 Jan 29 🕠 5:30–8:30 PM 📍 Downtown Toronto (DM for details) Our last event brought out ~50 SDR leaders across Canada, and this one is shaping up to be even more tactical. If you lead SDRs, coach reps, or own pipeline creation and want to sharpen how coaching actually works in 2026, DM me and I’ll send you the invite.

22

6 Comments

Why I Believe AI Will Define the Next Era of Enterprise Sales After two decades of building sales technology, I've learned one fundamental truth: the gap between average and exceptional sales performance isn't talent—it's infrastructure. I recently sat down with the CanadianSME Small Business Podcast for their episode "AI in Sales: Gamechanger for Revenue Growth" to discuss why we built servicePath™ and where I see the enterprise sales landscape headed. The reality facing most organizations today: Your sales teams are brilliant. Your products are strong. But your quoting process? It's likely costing you millions in leaked revenue, extended sales cycles, and pricing inconsistencies that erode margin. Legacy CPQ systems and spreadsheet-based workflows weren't architected for the complexity of modern enterprise sales. They're artifacts of a different era—and they're holding you back. What we covered in the conversation: ✅ How AI in Sales Operations is fundamentally accelerating sales cycles and massively reducing costly human errors. ✅ Strategies to immediately eliminate Revenue Leakage and optimize pricing for peak profitability. ✅ Exclusive insights into what Gartner recognition means and where the future of Sales Tech is headed. ✅ The successful roadmap for scaling a Canadian SaaS company, like servicePath™, into a dominant global enterprise solution. Here's what I'm most excited about: We're at an inflection point. The AI-native CPQ platforms emerging today don't just automate—they augment strategic decision-making. They compress deal cycles not by cutting corners, but by eliminating friction. They protect margin not through rigid rules, but through intelligent guidance. At servicePath™, we've transformed complex sales into intelligent, accelerated revenue streams for tech-enabled enterprises. This isn't vaporware or future-state thinking—it's delivering measurable results today. For my fellow CEOs and revenue leaders: If you're evaluating your sales tech stack, wrestling with quote accuracy issues, or watching deals stall in configuration complexity, this conversation might reframe how you think about the problem. 🎧 Listen here: https://lnkd.in/gnKWdvqc I'm curious to hear from this community: What's your biggest sales operations challenge right now? Where are you seeing the most friction between your sales team's potential and their actual execution? Let's talk about it. 👇 #Leadership #AIinSales #RevenueGrowth #CPQ #SalesTech #servicePath #CEO #EnterpriseAI #B2B #RevenueOperations #SalesLeadership #DigitalTransformation #CanadianTech

15

More SDRs won’t fix a broken pipeline. At scale, revenue becomes a design issue, not a staffing issue. Headcount amplifies systems. It doesn’t repair them.

4

The best sales reps in Web3 aren’t SDRs. They’re founders. Because they know the problem deeper than anyone else. But most founders hate outreach. They think it’s “not their job.” It is. Nobody will sell your product better than you, not until you’ve built the script through reps. You want better clients? Start by doing the calls yourself.

5

AI won’t solve a hiring mistake. ✅ Outreach can be automated ✅ Scheduling can be automated ❌ Drive cannot be automated Sales enablement tech only delivers results when it’s paired with the right people—the reps who take initiative, stay resilient, and keep pushing without needing constant direction. If you want to scale success (not mediocrity), check out our latest blog: AI Sales Enablement: A Multiplier for High-Drive Sales Reps. Link in comments 👇 #SalesHiring #SalesEnablement #SalesLeadership #AIinSales #SalesPerformance

2

1 Comment

Laura Canada — a 95-year-old family business with 140 stores across Canada — switched their entire operation to Shopify POS in one rollout. The challenges: • Century-old business, complex integrations • Legacy systems preventing innovation • Two brands on one backend • 12+ years on the same system • Duplicate data, constant firefighting The transformation: • All 140 stores switched successfully • 30-second order fulfillment (down from 5-10 minutes) • 95% of ecommerce fulfilled in stores • Clean data with built-in validation • Team shifted focus from firefighting to innovation Jennifer Pearson led this transformation with EY and shares incredible insights about change management, partnership, and what it really takes to modernize a historic retail brand at scale. Watch it here: https://shopify.link/ADzj   

80

1 Comment

STOP LYING TO YOURSELF THE PREDICTIVE REVENUE MODEL and THE MQL WATERFALL ARE DEAD As 2026 begins, one thing is becoming clear: volume-based GTM is no longer producing predictable results. More emails, more LinkedIn messages, more calls none of it guarantees pipeline the way it once did. Buyer attention is fragmented, algorithms filter most outreach, and decision-makers are harder to reach than ever. This isn’t a temporary slowdown. It’s a structural change. The teams that will win in 2026 aren’t the ones with increasing activity. They’re the ones aligning their GTM motion around who is actually in-market and when it makes sense to engage them. Intent and timing are no longer optimizations. They’re the foundation.

3

1 Comment

The top 10% of sales reps aren't 10x more talented.They're 10x more activated. The difference: • They find content in seconds, not minutes • They walk into calls with context, not confusion • They get surgical coaching, not generic training • They spend time selling, not searching That's not talent.That's capacity. And capacity can be unlocked. 5 days until we show you how. 🏆 #PresidentsClub #RevenueActivation #AgenticSales

25

Your pipeline isn't dry. Your volume is. Every time someone says "the market is quiet" I check their dials and it's like... 11 calls by Thursday 💀 The market isn't quiet. YOUR phone is. 100 dials → 15 conversations → 5 meetings → 1-2 closes. It's just maths. You don't need a better pitch. You don't need warmer leads. You need to pick up the phone 40 more times. The reps killing it right now? Same market. Same product. Same script. More volume. It's not a talent gap. It's a dial gap. Fix the input. The output fixes itself.

16

2 Comments

Buyer: Need a week+ to talk to our teams, then I can review the proposal. Rep: Sounds good! (adds SFDC task for three weeks from now) 😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑😑 One easy miss in creating urgency or speeding your deal to close is because we miss the chance to effectively nurture.   This is your chance to educate, add value, and stay in touch. Here's how I'd run my play:    1. Send a more customized thank you/understood note  2. Send an email to educate them the following Saturday morning   Sean, thinking through two things that might be good food for thought as you consider buying our #SMYKM Masterclass: - this post that says X and shows the correlation between my personalization and CXO meetings we book - this recent screenshot on the data of personalization over scaled/veiled  Hope it's helpful!   3. Tag them in the comments of a relevant post. "Sean, what I was just mentioning in last week's email!" 4. Send them another educational note, case study, or accolade." Morning! A client recently gave us a testimonial noting that our SMYKM training + sequence workshops netted them the same response rate as before - 9% - but doubled in positive replies from 13% to 22%, almost doubling their meeting bookings, and it also took their unsubscribe rate from 17% to 1.5%, all in three months. Makes me think of the positive impact we could have to your sales team, but also to marketing, if helpful! Key learnings here:   1. You're creating a drip campaign to educate them while they navigate internal meetings - give them ammo in meetings by educating them 2. Using multiple mediums to get their attention   3. You're making NO ask whatsoever - this isn't about you getting another meeting or an update on your proposal, it's about you educating them while you await those few weeks to pass   4. You're putting in the effort that other reps aren't. 5. If this helps marketing, you might have found another source of budget to move your deal along or grow it   6. Take the time to write a really great email and then keep that in a master Google doc of nurture emails that you can copy and paste through these next 12-18 months   7. After you send the email, pause and think, "Who else am I trying to win over on this product and who I can copy/paste this to?", rinse/repeat/nurture at scale #samsales #SMYKM

135

37 Comments

Dear revenue leaders and HR — Your SDR career track shouldn’t directly lead to SDR management without a different role before that 😒 It may feel like the right move short term to promote your SDR to SDR manager because 1️⃣ this is someone that is great at their craft and can teach this to other SDRs 2️⃣ give them the easy promotion path they maybe asking for But ultimately you are setting them (or yourself or the craft of sales) up for a tough career path long term. ✋🏽 Getting diversity of experiences — through a closing role (AE), or a farming role (CSM or AM) is key to getting hired for senior executive roles in their future. It also helps create the right talent funnel for your GTM org ✅ I strongly believe it’s the best path to building an amazing rev org. The truth — if someone hasn’t managed multiple parts of the funnel, they will have a harder time finding their path to owning the whole funnel as a C level exec 5-10 years down the road. Ofcourse there are exceptions to this rule — later career SDRs that have experience in different industries or folks that just LOVE the job. ✔️ But if you are hiring new grads into their first jobs — it’s your responsibility to help them explore different possibilities across GTM 🔑 Do the right thing for people’s careers 👊 Your job as a leader is to help your people excel in their role today while also helping them find their long term ‘why’ 💙 Thanks for coming to my ted talk 🙏

44

4 Comments