Average Deal Size Insights

"We need bigger deals to hit our revenue targets." Every VP of Sales says this. Then they discover what sucks about enterprise sales: As deal size goes up, win rates go down. Dramatically. Let's look at some super fun data to set the stage: - SMB ($5K-$25K): 35-45% win rate, 30-60 day cycle. - MM ($25K-$100K): 22-28% win rate, 90-120 day cycle. - ENT ($100K-$500K): 12-18% win rate, 180-270 day cycle - Strategic ($500K+): 8-12% win rate, 300+ day cycle. Now, the math gets fugly quickly: - SMB Rep: 40% win rate x 24 deals/year = 9.6 wins x $15K = $144K. - ENT Rep: 15% win rate x 8 deals/year = 1.2 wins x $250K = $300K. Sure, the ENT rep makes 2x the revenue. But look a tiny bit closer, starting with the risk analysis: - SMB rep: Predictable $144K +/- 20%. - ENT rep: Volatile $300K +/- 80%. And pair that with an ENT rep's reality: - Great year: $500K (2 big wins). - Average year: $300K (1-2 wins). - Bad year: $75K (zero wins). Versus a SMB rep's reality: - Great year: $175K (11 wins). - Average year: $144K (9-10 wins). - Bad year: $115K (7-8 wins). Which would you rather forecast? lol exactly. Look, we all know this, but worth repeating that as deal size increases, complexity explodes: - 4x more decision makers. - 5x longer cycles. - Higher budget scrutiny. - More competitors. Each factor multiplies the others. A $500K deal isn't 10x harder than $50K. It's 50x harder. Soooo what's a leader to do? Try building portfolios following the 60/30/10 rule: - 60% pipeline in reliable $25-75K deals (bread and butter). - 30% in growth $75-200K deals (stretch but achievable). - 10% in moonshot $200K+ deals (lottery tickets). You get base revenue from reliable deals, growth from MM expansion, AND upside from enterprise wins. Of course, be sure to build a specialized team. SMB reps need speed, process discipline, and volume management. Meanwhile, ENT reps need patience, relationship building, and the ability to navigate complexity. Don't try to have the same reps execute both motions...you'll just have a team that's mediocre at everything. tl;dr = bigger deals aren't better deals. They're different deals. Higher risk, higher reward, higher unpredictability. Before chasing ENT logos, ask yourself: - Can your team handle 85% rejection rates? - Can your forecast handle massive quarterly swings? - Can your pipeline handle 9-month cycles? If not, stay in your lane until you can. Because there's nothing wrong with winning consistently at $50K deals. But there's EVERYTHING wrong with losing consistently at $500K deals.

Bigger Deals. Smarter Bets. Between H2 2022 and H1 2025, the average office deal size in India has grown from ~36,000 sft to over ~ 62,000 sft (Source: Knight Frank). What does that tell us? Corporates typically take larger office spaces when they are consolidating teams into one hub, expanding due to business growth, locking in space ahead of future hiring, upgrading to premium campuses, or doubling down on long-term presence in strategic markets. Each move reflects clarity about business direction, workforce strategy, and India’s economic trajectory. Not that the cycle is always up. Not that risk has vanished. But that even amid uncertainty, large domestic and multinational occupiers are still placing calculated bets and choosing scale. This isn’t just momentum. It’s conviction, backed by optimism and a long-term view. And when average deal sizes rise, the entire market strengthens. Larger leases bring more stability. Developers get visibility. Investors get clarity. And tenants often lock in better assets, better terms, and longer commitments. It signals maturity, a market moving from transactional to strategic. In real estate, like in life, turning points are easiest to see in hindsight. But some trends speak for themselves.

A 15-rep fintech team. New VP of Sales. Six months in. He pulled up the last 30 closed deals. Average size: $32K. The ICP doc on the wall said $100K plus. The reps were closing deals 70% smaller than the company they were built to sell to. Pipeline looked healthy. Forecast looked clean. Quota was hitting. Revenue was 35% below where the same team should be producing. We pulled the qualification criteria the reps were actually using. Not the one on the wall. The one in the CRM. The one in their actual conversations. Reps were qualifying on company size only. Anyone with the right headcount could be an opportunity. Nobody was checking revenue band. Nobody was checking buyer authority. Nobody was checking budget signal. The 30 closed deals fell into two buckets. Sub-$50M revenue companies that bought the entry tier and never expanded. The $30K deals. $50M-plus revenue companies where the rep happened to land on a real buying committee. The $100K-plus deals. Same effort. Same product. Triple the ACV when the qualification was tight. Here is the fix we shipped. Three qualification gates. All required before stage 2. One. Revenue band confirmed by public source or asked directly. Two. Buyer authority named. If we don't have the title we sell to in the next two meetings, the deal pauses. Three. Budget signal. A line in the next-year plan, a recent investment in a similar tool, or a leadership ask. One of three. Eleven months later, win rate moved from 28% to 42%. Average deal size moved from $32K to $87K. That team added $1.4M in new revenue on the same number of reps, the same product, the same total leads. The qualification you skip is the ACV you lose. The ICP on the wall is decoration if the gates in the CRM are softer.

Where Did the Deals Go? The Quiet Retreat of Big-Ticket Buyouts In 2025, size isn’t strength—it’s exposure. Global private equity deal count dropped 11% last quarter. But the real story is what didn’t happen. Large-cap buyouts, once the headline-makers of the PE world, have taken a backseat. Despite an average deal size that looked higher ($576M vs. $400M in 2024), this is likely carryover from the optimism of late last year—not a sign of resurgence. Let’s be clear: the macro backdrop has changed. Rate uncertainty lingers. Tariffs and geopolitical shocks are dampening sentiment. And credit conditions remain tight. Here’s my view: This isn’t a collapse. It’s a recalibration. And smart capital is rotating toward smaller, more nimble transactions. What’s outperforming? - Mid-market deals with operational levers—not just financial engineering - Sectors with stable margins and low capex dependency - Regions where public markets haven’t fully priced in the policy risk (North - America stood out last quarter, but that resilience may not last) What we’re watching - Deal pipelines shifting to sub-$500M targets - Sponsor-to-sponsor transactions vs. trade sales - Regional divergence in deal momentum Investor action plan - Assess concentration risks: Are you overweight large, debt-heavy strategies? - Double-click on GP sourcing models: How are they finding deals in this environment? - Stay flexible: Consider mandates that allow both core and opportunistic deployment. In this market, being smaller means being faster—and smarter. #bealtetnative #alternativesforall

The state of co-selling, as told through a partner lens. The team at Omdia just concluded several global surveys targeting the "traditional" channel; The close to 500,000 resellers (VARs) and managed services providers (MSPs) who would have structured their early business economics around a point-of-sale (resell) motions with vendors. What we learned --> co-selling isn’t optional anymore. Fifty percent of partners say they co-sell with vendors frequently or very frequently. Another 23% do so sometimes. That means nearly three-quarters of the channel is engaging in some level of coordinated selling motion. But the real story is in the outcomes: --> When partners co-sell, deal sizes expand. Nearly 60% report larger average deal sizes, with 30% saying deals are significantly larger. Only 7% see deal sizes reduced. That’s not incremental lift — that’s structural upside. --> The close rates tell an even stronger story. 58% percent of partners report higher win rates when co-selling, with 30% seeing significantly higher conversion. Coordinated account mapping, shared data, executive alignment, and joint value propositions aren’t theoretical advantages — they’re measurable accelerants. In today’s buying environment — with an average of 13 stakeholders on the client side, longer cycles, and ecosystem-led decisions — no single seller wins alone. Customers buy from constellations, not companies. The takeaway for vendors? If your co-sell motion is unclear, underfunded, or overly manual, you’re leaving revenue on the table. The takeaway for partners? Proximity to the vendor sales engine drives pipeline gravity. Every partner (regardless of legacy type) is looking to grow pipeline, win larger deals faster, and with a much higher yield. Co-selling isn’t a tactic. It’s a multiplier.

How can you prove your newsletter’s influence on revenue? 🗞 NOT by reporting on platform metrics like opens, bounces, or click-throughs. If you want to seat at the revenue table, content teams need to connect newsletter investment to the bottom line. Here's how I do it in HockeyStack using multi-touch attribution and custom reports. I built this dashboard in 15 minutes :0 First up, core subscriber vitals at a glance: --> Subscriber growth Using a line chart to visualize historical growth, how many subscribers have you gained over a period of time? --> Cost per subscribers (paid ads) If you’re running paid ads to promote your newsletter, then how many of those clicks convert into subscribers, and at what cost? This will tell you how fast you can scale subscribers on your budget, but it will also give you a benchmark for how much each organic subscriber is worth. You can use that benchmark to budget for organic promotions like giveaways or partner referrals. --> Revenue per subscriber How much revenue have you generated all time from people who were subscribers first? Now divide that number by total subscribers to get your average revenue per subscriber. If a subscriber is worth $100 in revenue, you can estimate how much revenue a larger audience would produce in the future. -->Conversion lift of newsletter How much more likely are people to book a meeting if they’re a subscriber first vs. those who aren’t? Use HockeyStack lift analysis to estimate and visualize this automatically. If that number was closer to 0, then it would mean that your newsletter plays little role in driving new meetings. Next, core revenue vitals for your newsletter: --> Demo requests: how many subscribers requested demos in the last quarter? --> Closed/won: of those demo requests, how many converted into customers? --> Revenue: of those customers, how much revenue did they generate? --> Average deal size: of that revenue, what was the average deal size per subscriber? Last, how do your subscribers compare to non-subscribers? Multi-touch attribution has a few surgical use cases that I love. Mainly its ability to segment audiences based on touchpoints and buying behavior. In HockeyStack, I compare subs to non-subs in minutes using MTA touchpoint filters. Do they convert more? Less? Close faster? Slower? Spend more? Spend less? Compare close rates, average deal size, and sales cycle durations between subscribers and non-subscribers to see if your newsletter is building affinity and creating more efficient sales in the future. Link in comments for the full HockeyStack template and breakdown! What else would you add?!?

Since 2012: 4 distinct M&A phases in 15 years, yet 80% ended up in bonfire We continue our FY 2025 FMCG Results Series — following our full FY 2025 Publication. Looking at ~15 years of M&A activity of the world's largest FMCGs, we distinguish four main phases with very different M&A value, deal type/sizes & strategic objectives: Phase 1 (2012–16): Mega Mergers. $392Bn disclosed deal value, $1.2Bn average deal size, 636 deals. Big/mega deals, scale M&A on mature assets, focus on cost synergies. Dominant players: JAB HOLDING COMPANY LLC, AB InBev, Kraft Heinz, Procter & Gamble Phase 2 (2017–21): Adjacent/Digital/Start-Up M&A. $270Bn, $0.4Bn average, 959 deals. Rise of CVC/start-up bets, digital-first/DTC deals, acquirers entering adjacencies. Dominant players: Nestlé, PepsiCo, The Coca-Cola Company, Unilever Phase 3 (2022–23): Mid-Sized Scale Growth M&A. $42Bn, $0.4Bn average, 278 deals. Small/mid-sized deals, scale M&A on growth assets, capabilities M&A on the rise. Dominant players: JDE Peet's, Mars, L'Oréal, The Estée Lauder Companies Inc., Mondelēz International Phase 4 (2024–25 and beyond): Progressive M&A Bounce Back. $99Bn, $1.1Bn average, 130 deals. Mostly small-size deals and 2 mega (large-sized) deals. Scale M&A on mature assets. Dominant players: Mars and JAB HOLDING COMPANY LLC The shift in deal type tells the story. Phase 1 was 77% scale on mature assets. Phase 2 pivoted to 34% adjacent & 39% digital. Phase 3 moved to 59% scale on growth assets. Phase 4 is returning to 83% scale on mature assets — but with the lessons (and scars) of the $600Bn bonfire. The average deal size has come full circle — from $1.2Bn in Phase 1, down to $0.4Bn in Phases 2 & 3, and back to $1.1Bn in Phase 4. Mega-deals are returning. We predict Phase 4 will accelerate sharply through FY2026 — with family-owned firepower (Mars & Ferrero moving without Wall Street pressure) and PE/VC exits creating an unprecedented pipeline of available assets. Exciting times #fmcg #cpg

🚀 Digital Health in 2025: My Takeaways from the Latest CB Insights Report Just finished digging into the newly released CB Insights Digital Health 2025 report — and it’s clear: the sector has entered a new phase defined by AI scale‑ups, mega‑round dominance, and a sharpening focus on commercially mature players. Here are the five trends that stood out for me: 1️⃣ Funding climbs again — but deals shrink. Global digital health funding hit $22.3B (+19% YoY) even as deal volume dropped 9% to 1,474. The market is consolidating around fewer, larger, more conviction‑driven bets, with average deal size up 29% to $20.3M. The US captured 71% of all funding ($15.8B), reinforcing its dominance — and its median deal size jumped 33% to $8M. 2️⃣ M&A rebounds after three sluggish years M&A deals surged 33% YoY to 210, reversing a long decline. Notably: Thermo Fisher’s $9.4B acquisition of Clario was the year’s largest exit. Nearly 1 in 4 M&A deals targeted AI companies — a signal that proprietary models + proprietary data = defensible moat. 3️⃣ Mega‑rounds ($100M+) now rule the market 44% of all 2025 funding went to mega‑rounds — the second consecutive year of growth. Among them: ✅Oura’s $900M Series E, ✅Neuralink’s $650M, ✅Isomorphic Labs’ $600M. This is another sign of the market tilting towards scale‑ready players with validated traction. 4️⃣Mid‑ and late‑stage companies take center stage For the first time ever: ✅ Mid‑stage deals reached an all‑time high (19%), ✅Late‑stage grew to 11%, ✅Early‑stage dropped to a record low (59%). ✅Investors are clearly prioritizing path‑to‑revenue, commercial readiness, and clinical defensibility over experimental bets. 5️⃣ The AI wave reshapes the unicorn landscape The number of new unicorns nearly tripled to 14, and every single one of them is AI‑native — spanning: ✅drug discovery (e.g., Chai Discovery), ✅clinical documentation (e.g., Abridge), ✅provider intelligence (e.g., OpenEvidence). The message is clear: AI is no longer an “adjacent” technology — it is the new digital health infrastructure. 🔍 What this means for 2026 and beyond Across our ecosystem, this data reinforces what we’re seeing every day: AI‑first companies with proprietary data advantage are attracting disproportionate capital. Incumbents are accelerating inorganic strategies to buy capabilities rather than build them. Commercial maturity is becoming the new currency — headcounts, go‑to‑market capacity, and integration readiness matter more than ever. Europe continues to strengthen, led by standout rounds like Oura’s $900M Series E, while the US maintains absolute funding leadership. 💡 My closing reflection Digital health is entering a post‑hype, pre‑scale phase. The players winning today are those who combine: AI advantage + verified clinical impact + scalable business model. If 2025 was about consolidation and validation, 2026 will be about execution at scale. **Link to download the report in the comments**

When I started at Pipefy, our average deal size was $3,108. When I left it was $42K+. And no, I’m not going to make you comment “PLAYBOOK” to get the details. Here’s exactly how we did it 👇 1️⃣ The wake-up call. My first week, I saw three deals: $1K, $4K, $8K. Each had been in cycle for 4+ weeks. So… we were spending a month chasing deals that barely covered the AE’s Uber Eats budget. Hard pass. 2️⃣ Cut the noise. I told the team: “All deals under $5K are out of forecast.” If you want to work them, they better close in < 3 meetings or have real strategic upside. Otherwise, you’re just donating your time to Salesforce. 3️⃣ Add some structure. We implemented: - Force Management (on top of MEDDICC) - Joint Success Plans - Value Analysis - Deal Checklists Translation: we stopped winging it. 4️⃣ Focus where money lives. Top 20% of accounts = 80% of revenue. So we stopped treating every account like it was our favorite dinner recipe. 5️⃣ Move upmarket. We shifted focus to the 31% of accounts driving 85% of revenue. Everyone else? Self-managed. ✅ Milestone: by Oct ‘24, average deal size hit $15K. 6️⃣ Go see people. We got onsite with every managed account — most more than once. Shocker: face time > Zoom time. 7️⃣ Focus & niche. Five industries. That’s it. AI-enabled workflows for mid-sized teams. ✅ Milestone: by May, average deal size hit $42K. This stuff is hard. Like, “alignment between Sales, RevOps, and Product” hard. (So… basically herding cats with spreadsheets.) But here’s the truth: You don’t need perfection. You just need focus and consistency. 💡 Lesson: Revenue growth isn’t about doing more things. It’s about doing the right things, over and over, until people start copying you on #LinkedIn. Okay now you can comment playbook below and I will maybe give you a laugh reaction if I'm not too busy hogging the best conference room in the Gorgias SF office. Also we're #Hiring at Gorgias so hit me Luke Frigault Tanya Baptista Tam Djordje Maletic James Timperley up. #Sales #AI #LaughAtMyJokesMyMomThinksImFunny

"We're hitting our targets, but I know we're leaving money on the table" This is what the CEO of a $5M company told me last quarter He was right After a 2-day audit, we found his sales team was converting at just 3% of their true potential The culprit wasn't what anyone expected It wasn't: - Lead quality - Sales talent - Product features - Market conditions It was their PRICING ARCHITECTURE → They were selling "packages" instead of solving problems Here's what we discovered: When prospects said "it's too expensive," the team heard "lower the price" What prospects actually meant was "I don't see enough value FOR ME" We restructured their offers around specific business outcomes instead of features No more "Basic," "Pro," and "Enterprise" tiers Instead: "Revenue Accelerator," "Margin Maximizer," and "Scale Catalyst" Each tied to a specific financial outcome with tangible metrics The results? - Average deal size: Up 150% - Discounting: Down 50% - Close rate: Up 20% - Sales cycle: Shortened by 18 days All within 60 days of implementation The most shocking part? We didn't change their actual product OR their core pricing We just changed how they positioned value After 10 years helping companies grow, I've learned this truth: - Most sales teams aren't struggling with selling skills - They're struggling with value articulation Your prospects don't buy what you DO They buy what it means for THEM What would happen if you stopped selling features and started selling outcomes? P.S. If you need help with your sales, send me a message