Business Strategy

The shift from seats to agents pressures SaaS margins. At the same time, the longstanding practice of getting enterprise customers to pre-commit and also prepay for functionality they may never deploy will get harder as CIOs look to free budget for their own LLM costs. To weather the storm, some SaaS companies have increased prices. This boosts revenue and margins in the short-term but can't be done repeatedly and creates even greater scrutiny over shelfware as procurement teams right-size and shift contracts to "pay as you go." To achieve sustainable growth, SaaS companies need to become hyperefficient at sales and marketing. Here are common ways to do so and who's doing it well: 1. PLG. Shopify and Atlassian exemplify efficient go-to-market based on product-led growth with free trials, low-friction upgrades and upsells. Their sales teams only need to get involved in the biggest opportunities at the largest accounts; every other step in acquisition, commercial transaction, activation, onboarding, and growth is self-service and automated. 2. Vertical SaaS. Guidewire Software and Veeva Systems are laser-focused on insurance and life sciences, respectively. Rather than casting a wide net, they spear-fish with deep domain knowledge and purpose-built solutions for that industry's specific workflows and regulatory requirements. Guidewire doesn't need to buy Super Bowl ads– their annual customer conference is the Super Bowl for property & casualty insurance executives. Nearly zero GTM effort is wasted– unsurprisingly they're the two most efficient on the list. We modeled Hearsay Systems after both these companies, and this focus allowed us to win incredible market share among Fortune 500 banks & insurers despite only raising $60M in totality. 3. Relocate operations to lower-cost regions and AI. This is private equity's favorite playbook to take costs out of companies they buy. Field sales continues to shift more to Zoom, which means you can hire AEs anywhere. Inside sales contributes a greater % of revenue as PLG motions are established. AI handles top-of-funnel leads qualification and generating marketing content and campaigns. 4. Focus on gross revenue retention. Because of high customer acquisition costs in #SaaS, leaky buckets are margin killers. Use LLMs to help customer success teams analyze product usage, segment cohorts, and identify opportunities to increase value realization. Put in guardrails to prevent sales reps from overselling an account, as doing so only creates churn in the next renewal cycle. 5. Introduce another product line. This only works if your new product has the same buyer as your existing products. Many SaaS acquisition pro formas fail to actualize for this reason, as it's not actually feasible to have the same AE sell both old and new products. Every SaaS company right now needs to double down on one or more of these levers in the AI era.

I evaluate security investments using this matrix. See if it helps optimize your security budget: IT leaders often ask me how I prioritize security investments. Here's my actual 𝗦𝗲𝗰𝘂𝗿𝗶𝘁𝘆 𝗟𝗲𝗮𝗱𝗲𝗿'𝘀 𝗜𝗻𝘃𝗲𝘀𝘁𝗺𝗲𝗻𝘁 𝗠𝗮𝘁𝗿𝗶𝘅 I use with clients: Let's focus on the key quadrants that drive most decisions: 𝗛𝗶𝗴𝗵 𝗜𝗻𝘃𝗲𝘀𝘁𝗺𝗲𝗻𝘁/𝗙𝗮𝘀𝘁 𝗥𝗲𝘀𝘂𝗹𝘁𝘀 (𝗗𝗲𝘁𝗲𝗰𝘁𝗶𝗼𝗻 & 𝗥𝗲𝘀𝗽𝗼𝗻𝘀𝗲) ↳ EDR/XDR offers immediate visibility into threats ↳ SIEM provides correlation capabilities ↳ Consider these essential but not sufficient 𝗟𝗼𝘄 𝗜𝗻𝘃𝗲𝘀𝘁𝗺𝗲𝗻𝘁/𝗟𝗼𝗻𝗴-𝗧𝗲𝗿𝗺 𝗥𝗲𝘀𝘂𝗹𝘁𝘀 (𝗚𝗼𝘃𝗲𝗿𝗻𝗮𝗻𝗰𝗲) ↳ Security documentation establishes standards ↳ Metrics frameworks enable continuous improvement ↳ These deliver outsized ROI despite minimal investment 𝗜 𝗳𝗶𝗻𝗱 𝘁𝗵𝗲𝘀𝗲 𝗯𝗮𝗹𝗮𝗻𝗰𝗲𝗱 𝗶𝗻𝘃𝗲𝘀𝘁𝗺𝗲𝗻𝘁𝘀 𝗽𝗿𝗼𝘃𝗶𝗱𝗲 𝘀𝘁𝗮𝗯𝗹𝗲 𝘃𝗮𝗹𝘂𝗲: ↳ Vulnerability Management (moderate investment/balanced time-frame) ↳ Security Awareness (moderate investment/balanced time-frame) ↳ Next-Gen Firewall (moderate investment/moderate results) ↳ Identity Governance (higher investment/long-term value) Match your security investments to your organization's risk profile and operational maturity. Don't allocate budget based solely on vendor promises! I just guided a client to shift 20% of their budget from detection tools to identity governance. 𝗪𝗵𝘆? Their detection stack was great but identity controls remained basic. This created disproportionate risk exposure. 𝗧𝗵𝗶𝗻𝗸 𝗮𝗯𝗼𝘂𝘁 𝗶𝘁: The "best" security portfolio balances investments across 𝗮𝗹𝗹 domains shown in the matrix. What else would you add or change? --- Follow me Daniel Sarica for networking & cybersecurity frameworks

Here's how I treat intent signals + an example. TLDR - it's no different than how I treat any other outbound. The intent signal just gives me a reason to research the account. It isn't THE reason to reach out. Here's an example. Vanta announced their Series C funding today. If I received an intent signal from Vanta today, I wouldn't send them an email saying "Congrats on the funding! Noticed you were looking into training for your Sales team. I'd love to show you how I can help!". 427 sellers are probably sending them some version of that same email right now. Instead - I'd go to their funding announcement. I see: "Vanta plans to continue to go upmarket as it branches out from its startup roots" & "The company also plans to use the new funding to build out its AI products". Now, back to the problem I solve. Help sales teams stop losing pipeline to status quo. Now, I imagine how that problem might play out for Vanta. Moving upmarket = selling to companies who aren't as agile as startups. Companies who already have a way of solving the problem Vanta solves. Companies who might be more resistant to change the way they've always done it. And, it sounds like sellers will be getting more AI products/capabilities in their bags. An AI solution likely means more stakeholders will need to be involved to assess risk/privacy/etc. There's also varying degrees of skepticism in AI. Sales cycles may be slower as a result. Lastly, I'm looking for - what seems to be their maturity re: the problem/goal. The funding article references Atlassian, Omni Hotels, Quora and ZoomInfo as ENT clients. This tells me Vanta is having some success already. They're not trying to land their 1st ENT customer. Now, I take all of that context and write an email about my hypothesis. Subj: Christina's Comment Christina spoke about the move upmarket (building off the ENT wins w/ Atlassian, Omni, Quora). Not sure if you're seeing more stakeholders get involved in those ENT deals. The avg # for a complex deal is 11.2. Very different consensus requirements vs. a startup. More stakeholders = more buying group dysfunction. On avg, 40-60% of these opportunities end up lost to 'no decision'. GE taught their reps a different approach to get consensus with bigger ENT buying groups. Open to hearing how they did it? Jen Email #2 would be a similar format, but would tackle the AI problem hypothesis. I'd keep cycling through different problem hypotheses. Because as much as Vanta just became a prime target for us, the same can be said for everyone else with Vanta in their territory. Stand out with your insight + problem specificity.

DEI practitioners: unless the people we work with can clearly explain what #equity work means in the context of DEI, we're going to keep seeing organizations and laypeople alike having an easy target for their anti-DEI attacks. I don't want to see more infographics of kids standing on boxes. I don't want abstract metaphors or defining equity by what it's not ("equity isn't equality!"). These might be useful teaching tools to illustrate a concept, but something's deeply wrong when the people communicating in DEI's defense can't go any further than regurgitate metaphor when tested on their knowledge. How about: Equity is an organizational outcome where people's demographics no longer predict their success or failure. How about: We achieve equity for any given dimension of difference (race, gender, disability, sexuality, class, religion, parental status, etc.) when people across that demographic are hired, paid, given feedback, mentored, developed, and promoted fairly. How about: Achieving equity at scale within an organization requires that we remove discriminatory barriers to success, build processes and practices that are fair for all, and design policies that meet a wide range of differing needs. People should be using equity in the same sentences as "non-discrimination," "fairness," and "healthy organizations." People should be conceptualizing equity work alongside organizational design, participatory decision-making, and change management. Chew on that. Adapt it for your own context. Repeat it until you can say it reflexively, whenever you're pushed on the work you're doing, because this is one of the most straightforward ways we can take back the narative. Many of the ongoing attacks on DEI work opportunistically take advantage of this industry's inconsistent praxis and messaging. And unfortunately, the quippy straw men character assassinations of DEI propped up by these detractors are more readily absorbed by laypeople than "look at this graphic of kids on boxes to understand the difference between equity and equality." It's not enough for us, in this environment, to just do the work. We also need to defend it and train those we work with to defend it in the public sphere, to combat forceful misinformation with just as forceful TRUTH, asserting that we ARE seeking to undo and correct inequity precisely by building organizations that are healthier and fairer for EVERYONE—and that workplaces and leaders strike down this work at their own peril.

Small angel investors make the startup world go round - founders could be missing out by setting a high minimum check size. The SAFE has come to dominate angel / early startup investing, mostly because of decreased legal costs and time. So we looked at over 19,000 SAFEs signed by startups in 2023. All of these SAFEs went to companies that had yet to raise any priced equity. Some may be part of "seed on SAFE" rounds, others to true pre-seed companies. Small checks (under $25K) made up a full 62% of all checks signed in the earliest rounds (those under $250K total raised). Even rounds that came in just under $1 million had major participation from small checks. In fact, the median check size for all rounds $1 million or less never got over $25,000 last year. What do these small checks bring to a founder? Julian Weisser of On Deck suggests: 1. Expertise = They can help in a particular area (GTM, sales, hiring, etc).     2. Network = They can introduce you to other investors, potential customers, or future teammates.     3. Legibility = their involvement will help in the areas mentioned above and positively impact how other investors view your company. And sure, the total capital from these small checks may only account for a sliver of the total round. But they can demonstrate progress, push forward momentum, and the angels themselves may open doors to larger investors down the road. We are also seeing many initial advisors to nascent startups become strategic angels down the line. Lots of ways to improve your cap table. Here's to a year of small checks! Data just like this flows into 19,000 inboxes every Thursday morning - head over to the link in graphic to subscribe. #cartadata #startups #preseed #SAFEs #angelinvesting #founders

Ever heard of the Lippitt-Knoster Model for Managing Complex Change? It's a classic in the change management world, laying out the essential pieces needed to navigate big transformations. Taking a cue from that, I've adapted it to fit the world of digital transformation. There are seven key elements you can't afford to miss: Vision, Strategy, Objectives, Capabilities, Architecture, Roadmap, and Projects & Programs. Skip any one of these, and you're asking for trouble. Here’s why each one matters: • 𝐕𝐢𝐬𝐢𝐨𝐧: This is the 'what' of your transformation. A clear vision gives everyone a target to aim for, aligning all efforts and keeping the team focused. • 𝐒𝐭𝐫𝐚𝐭𝐞𝐠𝐲: Think of this as the 'why' and 'how.' A solid strategy explains the logic behind your vision, showing how you plan to get there and why it's the best route. It’s designed to guide everyone in the company on how to make decisions that support the vision, aligning all efforts and keeping the team focused. • 𝐎𝐛𝐣𝐞𝐜𝐭𝐢𝐯𝐞𝐬: These are your milestones. Clear, specific objectives make it easy to measure success and ensure everyone knows what's important. Without them, you can easily veer off course and waste resources. • 𝐂𝐚𝐩𝐚𝐛𝐢𝐥𝐢𝐭𝐢𝐞𝐬: These are what your company will now be able to do that it wasn't able to before in order to achieve the objectives. These can be organizational capabilities (like improved decision-making), technical capabilities (such as real-time operational visibility), or other types like enhanced customer engagement or streamlined processes. • 𝐀𝐫𝐜𝐡𝐢𝐭𝐞𝐜𝐭𝐮𝐫𝐞: A robust architecture ensures all your tech works together smoothly, preventing inefficiencies and costly headaches. This includes various types of architecture such as data architecture, IT infrastructure architecture, enterprise architecture, and functional architecture. Effective architecture is central to reducing technical debt and aligning software with broader business transformation goals. • 𝐑𝐨𝐚𝐝𝐦𝐚𝐩: Your roadmap is the game plan. It lays out the sequence of actions, helping you avoid uncertainty and missteps. It's your guide to getting things done right. • 𝐏𝐫𝐨𝐣𝐞𝐜𝐭𝐬 & 𝐏𝐫𝐨𝐠𝐫𝐚𝐦𝐬: These are where the rubber meets the road. Actionable projects and programs turn your strategy into reality, making sure your plans lead to real, tangible outcomes. From my experience, I think '𝐂𝐚𝐩𝐚𝐛𝐢𝐥𝐢𝐭𝐢𝐞𝐬' and '𝐑𝐨𝐚𝐝𝐦𝐚𝐩' are the two most overlooked. What do you think? ******************************************* • Follow #JeffWinterInsights to stay current on Industry 4.0 and other cool tech trends • Ring the 🔔 for notifications!

Every founder has a slide that says, “We’ll acquire customers through content marketing, paid social or partnerships.” And in 2025, nearly every investor has learned to ignore it 😿 The old go-to-market playbooks are not working anymore. The channels are saturated, the costs are high and the returns are diminishing. From where I sit as an early stage investor, a generic GTM plan is no longer a sign of preparation - it’s a red flag. It shows a founder is ready to execute someone else’s old strategy, not discover a new unique one tailored to their own business. Founders who are successful finding their first customers and raising capital are demonstrating something else entirely - not a polished plan, but a series of insightful discoveries. Here’s what I see actually working to prove you can access a market: ✔️ A Portfolio of Scrappy Experiments. Before you can find a scalable channel, you need to prove you can find ANY channel. The most impressive founders show up with stories of things that don't scale. They acquired their first 50 users by building a free tool that solved a tiny problem for their target user or by personally engaging in a specific Subreddit or Slack community. This proves you have the creativity and grit to find customers where others aren’t even looking. ✔️ A Founder Who Is the Distribution Channel. Early on, your most powerful GTM advantage can’t be bought because it’s actually YOU. Investors are looking for a founder with a unique ability to reach the market. Are you an expert with a following in your industry? Have you built a deep, trusted network that represents your initial customer base? Show how your personal brand and unique insights give you an unfair advantage that no amount of ad spend or marketing can replicate. ✔️ Mastery of a "Micro-Funnel." Instead of a broad, leaky funnel, demonstrate that you can dominate a tiny, efficient one. Prove that you can convert a very specific persona from a very specific source with incredible efficiency. For example: "We can turn a clinical research coordinator from a specific LinkedIn group into a qualified lead for $15." This level of precision is far more impressive than a vague, top-down plan to capture a massive market. It shows you have a data-driven foundation from which to grow. The goal of an early-stage GTM isn't to prove you can scale, it's to prove you can learn. Your first GTM strategy shouldn't be a playbook - it should be a lab notebook full of weird and (hopefully) winning experiments. 🙌🏼 Shout out to Alex Iskold from 2048 Ventures for teaching me a lot about funnels over the years and what he calls 'magic moments' 🙏🏼

How to sell (without feeling salesy): First, understand the Ethical Wealth Formula: (Value First × Trust Building) × Authentic Positioning  ———————————————————  Frequency of Asks × Pressure Tactics This isn't abstract theory. It's practical math: • Increase the numerator: deliver more value, build more trust, position more authentically • Decrease the denominator: reduce frequency of asks, eliminate pressure tactics • Watch revenue soar while your integrity remains intact Ethical doesn't mean unprofitable. It means sustainable. Principle 1: Value-First Monetization The approach that generates $864,000 monthly without a single "hard sell": • Deliver so much value upfront that buying feels like the obvious next step • Create free content so good people say "If this is free, imagine what's paid" • Solve small problems for free, big transformational problems for a fee Give until it feels slightly uncomfortable. Then give a little more. Principle 2: Trust Through Consistency I've never missed weekly content in 3 years, through vacations, illnesses, market crashes. The trust-building machine that works while you sleep: • Show up reliably when competitors disappear during tough times • Do what you promise, when you promise it • Maintain quality across every touchpoint One founder implemented this and saw conversions increase 74% in 30 days, without changing offer or price. Trust isn't built in grand gestures. It's built in boring consistency, most won't maintain. Principle 3: Authentic Positioning The approach that helped me raise prices 300% while increasing sales: • Own your expertise unapologetically, confidence is not arrogance • Speak to specific problems you solve, not vague benefits you provide • Tell detailed stories of transformation instead of listing features You don't need to be perfect to sell effectively. You need to be authentic about how you help. Principle 4: Invitation Vs. Manipulation The ethical alternative to high-pressure tactics: • Invite people when they're ready, don't push when you're ready • Create genuine scarcity (limited capacity) not fake urgency (countdown timers) • Respect "no" as "not now" rather than objection to overcome My most profitable sales sequence has zero countdown timers, zero artificial scarcity, zero pressure. Ethical selling feels like extending help, not hunting prey. — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. Want to improve your sales strategy? Join our community of 172,000+ subscribers today: https://lnkd.in/eTp4jain

Companies and their CEOs obsess over Profitability KPIs. But measuring Profit doesn’t drive Profit. Here’s the problem: Most leaders don't track the right metrics. They don't understand why they matter. They ignore stakeholder perspectives. If you don’t know and act on what the numbers are telling you - you’re not managing profitability. You’re just collecting data. Let’s fix that. Here are 16 Profitability KPIs every CEO and CFO needs to master—and how to extract the insights that drive smarter decisions: ■ Efficiency and Margins 1// Gross Profit Margin Ratio ↳ Why it matters: high margins signal strong pricing power or cost efficiency. 2// Contribution Margin ↳ Why it matters: critical for setting prices, understanding break-even points, and ensuring your products are profitable. 3// Operating Profit Margin Ratio ↳ Why it matters: reveals how well you’re managing core expenses 4// Net Profit Margin Ratio ↳ Why it matters: measures whether your business model scales profitably. 5// Return on Assets (ROA) ↳ Why it matters: shows how effectively your assets generate profit. 6// Return on Equity (ROE) ↳ Why it matters: measures investor return on their investment. 7// Return on Investment (ROI) ↳ Why it matters: helps prioritize high-ROI projects and avoid initiatives with weak returns. 8// Return on Capital Employed (ROCE) ↳ Why it matters: indicator for how well your business uses all available capital to drive profits. ■ Earnings and Market Performance 9// Earnings per Share (EPS) ↳ Why it matters: tells shareholders how much value each share represents. 10// Price-to-Earnings (P/E) Ratio ↳ Why it matters: gauges whether your stock is fairly priced based on earnings. 11// Dividend Yield Ratio ↳ Why it matters: income-focused investors seeking regular returns. 12// Dividend Payout Ratio ↳ Why it matters: balances reinvesting for growth with rewarding shareholders. ■ Cash Flow and Productivity 13// Operating Cash Flow Margin ↳ Why it matters: shows how well you convert revenue into cash. 14// Profit Per Employee ↳ Why it matters: tracks workforce productivity—a crucial metric for scaling efficiently. ■ Advanced Profitability Metrics 15// Economic Value Added (EVA) ↳ Why it matters: measures value above the company's cost of capital. 16// Break-even Revenue ↳ Why it matters: knowing your break-even helps you set realistic sales targets and avoid losses. The takeaway? Stop chasing KPIs for the sake of it. Start using them to lead smarter and grow faster. Want to join the 1% of CEOs who lead with financial intelligence? ▷▷▷ Join me tomorrow for a free webinar for CEOs, VPs, Managers, and leaders and start making 100% better business decisions: https://bit.ly/ceojan18 ▷▷▷ Transform your financial acumen in 6 weeks - live program, spots are limited, starts January 29: https://bit.ly/3ZCI0kr ♻️ Like, Comment, Repost if this was helpful. And follow Oana Labes, MBA, CPA for more

B2B SaaS revenue growth rates have slowed by over 50% in the past 2 years. And CAC Payback periods have skyrocketed by nearly 100% in the same period. These two effects combined put massive pressure on core financial metrics, business profitability, and enterprise value. The root cause of this is Go-To-Market Bloat (GTM Bloat) where B2B companies invest significant money in Sales & Marketing and do not get the appropriate return on investment. Sales & Marketing is by far the largest expense on a B2B company P&L - on average 40%-60% of total revenue; and 2-3X more than they spend on Product Development, Engineering, and R&D combined. GTM Bloat occurs across the entire go-to-market, including People, Programs, Process, and Technology. (1) People - Too many headcount on each GTM team, caused by outdated financial planning models, in addition to the overspecialization of roles on GTM teams (SDR, MDR, Solutions Consultant, AE, Onboarding Manager, CSM, AM, etc.). Or 90-person Marketing team that should be 35 people. Average sales quota attainment of ~40% is another clear indicator of headcount bloat. (2) Programs - This mostly happens in the Marketing budget. B2B companies dramatically overspend on large scale events and digital performance marketing - up to 15% of total revenue - and do not get anywhere close to an appropriate measurable ROI on these significant expenses. (3) Processes - Teams, meetings, reporting cadences to support programs that don’t work. SDRs to follow up with “leads” and get a meeting less than 1% of the time. Inefficient processes create significant bloat especially when operated at scale. (4) Technology - Buying an ABM tool for $200k per year and barely using it. So much bloated headcount increases license & seat costs for all SaaS subscriptions by 2-3X. Too many $100k+/year point solutions used by 1 department or team and not integrated or essential to the full GTM. __ Solving GTM Bloat is the #1 opportunity in a B2B company today to increase enterprise value. This is now a CEO, CFO, and Board Level issue. Eliminating GTM expenses that do not provide appropriate ROI could increase EBITDA by 20% or more. Restructuring the existing investments in GTM to deliver the appropriate effectiveness could increase growth rates by up to 2X (e.g. from 18% to 36% YoY). Or more than likely, the solution is a mix of both of these - eliminating low ROI expenses to improve EBITDA and doubling down on strategies that are already working to create breakthroughs in growth rate. #gtm #gotomarket #finance #b2b #sales *Benchmarks on public SaaS growth rates and CAC payback periods ℅ David Spitz and BenchSights. Shoutout to David for some of the best work in the industry connecting GTM with Business Financial metrics based on actual data (not surveys or inaccurate aggregated data). **At Passetto, we see similar, yet more amplified trends in our standardized analyses of CRM & Financial Metrics of private middle-market B2B companies