Jay Simons

Hot Take�� RIP #PLG, Long Live #SLG But before you throw shade, let me explain… 🔹 There are undoubtedly exceptions, I’m sure many will highlight monday.com, Freshworks, etc. 🔹 PLG works well for low ACV deals with low CAC… think SMB and mid-market customers. Target CAC payback <12 months 🔹 PLG is a fantastic top of funnel marketing channel for enterprise sales ⭐ But for 6-figure enterprise sales, you need enterprise salespeople pressing the flesh with customers

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Perfecting your product and GTM strategy are surely important. But Box CEO and co-founder Aaron Levie argues there's one factor that outweighs all others in startup success: recognizing and capitalizing on tech and macro tailwinds. Fighting against them? You're setting yourself up for failure. Our full conversation here: https://lnkd.in/gEAPFR-A

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As a founder and CEO, I’ve learned that true founder-market fit isn’t just about understanding your industry, it’s about the tenacity to push through when the inevitable challenges hit. Budget freezes, talent moves, customer churn, investor pullback, lost sales, and product or service quality issues are all part of the journey. Startups aren’t linear; the road is bumpy, and you need to be ready to navigate the unexpected. Building startup businesses in any sector is difficult but surviving and thriving in the technology arena is not for the faint of heart. You can have the best product-market fit in the world, but without the grit to keep going when constant change is afoot, key talent departs, or when you lose a big deal you thought was in the bag, it won’t matter. Your deep understanding, experience, expertise and comfort of the market gives you an edge, but it’s the ability to adapt, stay committed and push forward every day that ultimately drives success. Tenacity isn’t just a trait... it’s the backbone of every successful founder. It’s waking up every day, hungry to improve, iterate, and win. A results and outcomes disposition is key. Founders who embrace the uncertainty and keep the faith are the ones who move industries forward.

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𝗔𝘁𝘁𝗲𝗻𝘁𝗶𝗼𝗻 𝗜𝗻𝗱𝘂𝘀𝘁𝗿𝘆-𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰 𝘀𝗼𝗳𝘁𝘄𝗮𝗿𝗲 𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀! We're conducting a benchmarking study to define success metrics specifically for vertical software companies. 𝗪𝗵𝘆 𝗧𝗵𝗶𝘀 𝗠𝗮𝘁𝘁𝗲𝗿𝘀: Existing SaaS benchmarks just don't cut it for your unique industry needs. This research will provide the data-driven insights to measure and optimize your vertical software business. 𝗖𝗮𝗻 𝗬𝗼𝘂 𝗛𝗲𝗹𝗽? A few minutes of your time can make a big difference.

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2 Years ago, I set out to be more helpful. Being a devoted fan of technology companies at every stage, I set out to help companies at all sizes get better. I’ve always believed in the power of momentum, and that tactics inform strategy — not the other way around. The sooner you identify winning behaviors, the sooner you can double down on them, start to build momentum, and move faster toward your goals. I’m launching The Progress Advantage (https://lnkd.in/gRXS2xzr) as a place to share my thoughts and experience on this new era of GTM, for anyone who is interested. Sometimes these will be the product of some mid-flight plane thoughts. Other times, they’ll be tactical guides to implementing GTM strategies. Either way, these resources will always be free and ungated — meant for sharing, and learning together, and starting conversations. Thank you to all the founders and operators who put their trust in me and have given me the opportunity to do my life's work! And for those founders who need a bit of consultative help along the way, I’m happy to chat further about your specific needs — or to help dig into what’s keeping you from your next phase of growth.  Follow The Progress Advantage , we are just getting started! #alwaysbehelping

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Winning early GTM via founder led sales is an essential step in building a consequential start up. 🎯 But, while there are countless conferences focused on scaling GTM once you've hit a couple million in revenue, to date there hasn't been a conference focused on FOUNDER LED SALES and nailing the earliest days of GTM. 👀 😅 That ends now. 🙌 Pear VC has helped 100+ founders learn how to sell, how to build their 0-to-1 sales engine, how to get from $0 ARR to $1M ARR -- and now we're introducing the first ever GTM CONFERENCE for EARLY STAGE FOUNDERS. ⭐ "Zero to $1M: Winning Early GTM" will be held in San Francisco, CA this September 5th! ⭐ If you're at the idea 💡, pre-seed 🌰 , or seed stage 🌱 , this is the GTM conference for YOU. Come hear from Pear veterans, industry leaders, and successful repeat founders like Sanjit Biswas (Samsara and Cisco Meraki Co-founder and CEO), and leave with actionable guidance to supercharge your startup’s revenue from day 1. ​ ➡ APPLY NOW! Space is limited, and the early application deadline is July 15th. Pepe Agell and I will review applications on a rolling basis. 🚀 CANNOT WAIT TO SEE YOU THERE! 🚀 #earlystageGTM #zeroto1M #founderledsales

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We use Circle for our community at Exit Five, and Matthew Carnevale has become a Circle power user (he runs our community). They did this awesome write about how to grow a community with insights from Matt and Exit Five sprinkled in. • How to use your community as an audience growth multiplier • 5 systematic community growth strategies • Why you should treat your community like a product, and • Best practices for growing your community https://lnkd.in/e9vs32NQ

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This post for Alix Partners, on emerging pricing metrics for SaaS providers, is definitely worth reading. Two operational watch-outs for software companies heading down this path: 1. Not every customer will be willing to share every advanced metric (e.g., new customers signed up, customer care calls resolved, etc.) -- that has to be negotiated as part of a contract 2. Not every vendor's billing systems can meter and monetize every possible unit of consumption. Ideas that look great on a whiteboard often get eaten for breakfast by legacy IT! https://lnkd.in/ehjBKqG4

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Operationalizing warm introductions at scale doesn’t mean subscribing to TeamLink to see all the “connections” within your company. It means making the discovery and integration of “trust” signals (which unlocks access) an essential part of the sales process and daily GTM motion. This requires “push” vs. “pull” technology, where real relationships are distinguished from stale “connections” and where the intelligence is automatically mapped to target accounts in your CRM.  A system that intelligently notifies worthy connectors when one of their relationships can make a difference between winning or losing an important deal vs. finding out later that the AE missed it because a relationship was hidden from view. This drives a “relationship-first” approach for active deals in the pipeline and removes the ambiguity from ad hoc intro requests. In turn, this gives AEs the ability to request introductions with more confidence and credibility and gives everyone in the company a chance to participate in growing the business. As important, this “access through trust” approach should have a system to measure and quantify it effectively so the business impact (in $$) is clear to everyone and justifies the investment.  With relationship mapping becoming a bigger priority for teams heading into 2025, leaving these warm intros to chance and expecting AEs to both discover and decode real relationships from "connections" is a missed opportunity.

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What is a VC looking for? How about slowing down for a second—and asking some questions! Yesterday, I had the privilege of earning a few moments with Ryan Pruitt, despite his packed schedule. Ryan exemplifies true class and character. He’s not just a VC; he’s a partner who genuinely wants to help founders grasp what really matters. In just 45 minutes, he brought me a level of clarity that I hadn’t expected. I walked away with a clear sense of what to prioritize—what truly counts as a “win” versus what’s just noise in the journey to secure a first funding round. Here’s the big takeaway: Rule #1 – Treat VCs with respect, not as pitch targets. When you do, you’ll find they’re more eager to help than you ever imagined! P.S. Tag someone who should hear this today! #VentureCapital #StartupFunding #FounderTips #EntrepreneurMindset #VCAdvice #StartupJourney #FounderLife #BusinessGrowth #FundingTips #InvestorRelations

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Cap Table guidance from Cake Equity and my former colleague Chris Hoffmann, ECA 🚀🧢 VALUATION & EQUITY MANAGEMENT: Companies should aim for balanced equity plans that are fair yet practical, involving vesting schedules to ensure employees earn their shares. Giving employees sufficient time to exercise options post-vesting can also prevent punitive exercise costs. This approach encourages loyalty and values employee contributions without overwhelming the cap table. HIGH ADMIN DEMAND IN LATER STAGES: In growth phases, especially Series C and D, managing cap tables becomes complex, with frequent hires, exits, and equity grants. Software platforms (e.g., Cake) are essential to keep cap tables organized, as manual systems like Excel can't handle the volume and complexity efficiently. IMPORTANCE OF DAILY & MONTHLY AUDITS: Regular audits are crucial to keep track of terminations, new grants, and board consents. Errors in terminations and grants can lead to costly issues during audits, financial reporting, or funding rounds. SECONDARY TRANSACTIONS & LIQUIDITY OPTIONS: Allowing limited liquidity for employees and early investors, such as through tender offers or company-facilitated secondary transactions, is valuable. These mechanisms offer flexibility without requiring a full exit or IPO, which has become less common due to the IPO market slowdown. CAP TABLE ERRORS CAN BE COSTLY: Historical errors in cap tables can create major headaches. Two examples highlight this:    - In one case, a series D company had to spend $100,000 to $150,000 on cap table corrections, which delayed planned transactions by six months.   - Another company had converted multiple financing rounds incorrectly, requiring a year and a half of back-and-forth with attorneys and investors to correct the errors. These situations emphasize the need to organize and verify cap table data from the outset to avoid costly fixes later. RECOMMENDATIONS FOR FOUNDERS: Early-stage companies should seek expert help in setting up and maintaining cap tables, even if through fractional CFOs or specialized attorneys. Organizing all equity-related documents digitally, using reliable software, and conducting regular audits can save time, money, and stress in the long run.

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I recently shared that one of my favorite parts about working at Amplitude is the fact that despite being a public company, it still feels like a startup. And I think one of the key reasons for that is the high sense of ownership that everyone here has. Ownership is one of our core company values, and I love being able to see it in action every day. I share more below:

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Big news hit the GTM and partnerships world last week with the announcement of the Crossbeam x Reveal merger. As a long-time customer of Reveal, I couldn’t be more excited about these two companies coming together. Not only does the merger create a powerful network of 25K+ companies, but it also brings significant advantages to the Glassbox team by streamlining our time and resources, eliminating the need to navigate between separate systems. As a result, we can focus more on strategic initiatives rather than platform management. This is powerful for our partners, too. Having all partner data and insights in one place ensures a seamless and consistent message to our partners, enhancing our collaboration and efficiency. Here’s how I foresee the merger enhancing the key Ecosystem-Led Strategies we’ve been running in Reveal: 📊 Data-Driven Decisions At Glassbox, data is the backbone of every decision we make. Reveal and Crossbeam are indispensable for qualifying every partner, ensuring we see the ICP fit and opportunity sizing clearly. The expanded network will provide even more data insights. 🎯 Strategic Partner Alignment Reveal helps us understand which verticals best align with our partner GTM and enablement strategies, making our partnerships more strategic and effective. The unified company could provide us opportunities in new verticals. 🗺️ Enhanced Account Mapping The excitement around account mapping and opportunity plays is palpable. Reveal allows our reps to collaborate with partners on target accounts and support partners on their targets, enhancing mutual success. The combination with Sales-focused features with Crossbeam will amplify these plays ten-fold. 💰 Unlocking New Opportunities and Revenue Reveal identifies accounts not on our radar and even closed lost accounts, providing immense value in generating net new revenue from technology relationships and opening doors in unexplored enterprise divisions or countries. And, you guessed it, more data = more new opps. 🌐 Holistic Partner Ecosystem We can bring technology partners from our program to assist our solution partners on deals when they face challenges, creating a holistic partner ecosystem that drives success. 🤝 Unified Network Advantage: The unified strategy/platform with Crossbeam's acquisition of Reveal amplifies our capabilities, offering a robust account mapping and opportunity play solution that is critical to the Glassbox Partner Network (GPN). 🚀 Driving Digital Transformation: With the launch of the Glassbox Partner Network, Reveal and Crossbeam are crucial in driving enterprise digital transformation with AI-powered CX solutions, empowering us to achieve new heights in partner collaboration and revenue generation. I personally can’t wait to see how this unified strategy and platform will enable us to drive more effective account mapping, opportunity plays, and ultimately, greater success in our partner GTM and enablement efforts.

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Jared Barol, former Head of GTM Strategy at Salesforce and Reputation, joined me on the GTM Secrets podcast by Identity Matrix. This guy knows his stuff. We discussed balancing innovation and focus, competing at the highest level, and market penetration. Jared was awesome to have on. Go check out the full episode on every major podcast platform. Link in the comments! #saasmarketing #marketing #gotomarket

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There’s no one-size-fits-all approach to scaling a business, but the key is making intentional decisions about how you choose to grow. 🥾 Bootstrapping gives you control but might mean slower growth 🏦 Venture capital fuels fast growth but comes with trade-offs 🔋 A hybrid approach can balance both—but it requires discipline. At York IE, we believe that your growth strategy should reflect your goals, values, and market reality. Don’t chase hypergrowth for the sake of it. Be pragmatic, preserve optionality, and stay in control of your company’s fate.

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Many SaaS solutions resonate most with directors/VPs/department heads. For the past 5+ years the approach for selling to these folks was to get them very excited about your solution and price in such a way that they could get a deal done with minimal sign off. In enterprise this could run as high as 500k. Now, there is scrutiny on 25k deals. Smart sellers realize this and are running a totally different play. A little different flavor of the traditional top down model. These folks are still doing well. Folks running the old playbook? In struggleville. P.S. - when times are hard it’s actually easier to do big deals…if you know how to sell transformations.

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🚀 Venture debt covenants might sound like a small part of the deal, but they carry huge implications for your startup’s future. 📈 You need to be strategic in your negotiations to avoid any pitfalls down the road. It’s all about setting yourself up for success, not stress. Dive into more details in the original Kruze Consulting post. The link is in the 1st comment. 👇

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When you're not in the board room, you're always wondering, "What's going on in there?". I have now worked with seven companies where I'd regularly present to a board, a mixture of PE and VC-led, and it's almost always centered around a few key topics. If you're meeting your numbers: - what's your future forecast  - how are you going to continue to grow - how will you grow faster and more efficient  - update on money in the bank and spend If you're not meeting your numbers (along with the things I mentioned above): - what is your plan to turn things around and meet your numbers (this includes new logo, back-to-base sales, and churn reduction) - what resources can they offer to help - do you have the right players in the right seat This is an oversimplification because many nuances are at play, but this is generally it. While board meetings can be stressful, almost every board I've worked with wants to be helpful. Of course, their interest is, first and foremost, that the business is healthy and growing, so there's always that undertone, but overall, they want to help. After all, they are guardians of the investments they make on behalf of others and have to report back on their performance. Think of them like they are CSMs for their investors (the folks that give them money). They need to get a great return on the investment they made on their behalf.

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Channel partnerships are making a comeback, and it's time to take notice. When I first entered the VC scene, many investors - myself included - steered away from channel sales. The rationale was clear: we craved control over sales processes, the ability to engage directly with customers, and ownership of the customer relationship. But now that capital is both scarce and expensive, the tide has turned. Channel partnerships are experiencing a resurgence as teams reassess their approach to sales. In the past, concerns about relinquishing control and diluting messaging deterred companies from embracing channel partnerships. However, the financial constraints facing businesses today have forced a reevaluation of this stance. Now that it’s untenable to maintain large in-house sales teams, channel partnerships look like a viable - even appealing - alternative. And channel partners themselves are feeling the crunch, too. Where massive channel companies may have once housed behemoth R&D teams who fed their sales reps tens of solutions at once, they’re scaling back - leaving reps open to selling products they might not have previously considered worth their while. Companies and channel partners alike are thus starting to recognize the value of working together to extend their reach and drive revenue growth. But how long will this window of opportunity remain open? It's difficult to say, but one thing is certain: for companies looking to expand their market presence and drive revenue growth, the time to explore channel partnerships is now.

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