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FROM GTM TO PREDICTABLE ARR TO EXIT
Growth looks strong on paper.
But it’s not…
Growth looks strong on paper.
But it’s not…
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Articles by David
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How CROs Should Think About Exit-Driven Growth
How CROs Should Think About Exit-Driven Growth
Most CROs are hired to drive revenue growth. But the best CROs understand something different: Revenue alone doesn’t…
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GTM Strategy in 2026
GTM Strategy in 2026
(Based on an article by Demand Revenue) In 2026, a well-defined go-to-market (GTM) strategy for private equity (PE)…
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Reflections on the Olympics with Respect to Software Business Leadership
Reflections on the Olympics with Respect to Software Business Leadership
Watching the Olympics always reminds me that greatness is rarely about raw talent—it’s about discipline, preparation…
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David Gersh reposted thisDavid Gersh reposted thisWe've just released the ultimate playbook. What's working, what's dead, how to win in 2026 on LinkedIn. Every Sunday, you'll get exclusive access to it (for free): Here's what you get: • 5 post templates with real examples and breakdowns • 3 micro-playbooks for content creation insights • 1 creator spotlight a Q&A with top creators Jake and I have been working on this for months. Everyone keeps on "breaking down" how people are winning, but there's something missing... The creators themselves telling us how they did it. Because everyone can see the content and offers... But no one sees the behind the scenes... we do. So we're pulling back the curtain. No gatekeeping. Every Sunday. Straight to your inbox. Start the week knowing exactly what to post and why it'll work. 46K+ already got the first edition last Sunday (repost ♻️ this so we send you it too) Sign up for free at https://kleo.so/newsletter P.S. You'll also unlock 4 free gifts instantly, including prompts for viral posts, lead-gen posts, and soo much more!
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David Gersh shared thisHappy Wednesday! And aside from April Fools Day, today is my new "Secret Sauce Day"... Today's secret sauce for technology sales leaders and salespeople is a MUST-HAVE tool to ensure sales forecasting predictability: The Engagement (or Close) Plan is a documented, actionable, collaborative roadmap between a seller and prospect that outlines key steps, stakeholders, and timelines necessary to finalize a deal in a timely manner, increasing efficiency and trust. It includes milestones like contract review, legal approval, and procurement to prevent delays and ensure alignment. Key Components of a Sales Engagement Plan: • Defined Milestones: Specific dates for technical validation, legal review, and final signing. • Stakeholder Identification: Mapping out all decision-makers, champions, and blockers. • Actionable Next Steps: Clear, mutually agreed-upon actions for both the seller and the buyer. • Document Checklist: A list of all required paperwork, such as master service agreements (MSAs) or purchase orders (POs). Steps to Create an Effective Engagement Plan: • Collaborate with the Buyer: Introduce the plan early (ideally during the first qualifying call) and build it together with the prospect to ensure mutual agreement. • Define Goals & Value: Explicitly list the prospect's goals and map your solution to their business value. • Identify Potential Roadblocks: Proactively address potential technical, legal, or budgetary obstacles. • Set Clear Deadlines: Assign owners to each step with specific dates for completion, and refer back to the shared document at every agreed-to stage deadline. • Use a Shared Format: Comment "Engagement Plan" below, and I'll send you my Microsoft Word template to edit and share/mutually own with prospects. Or, you can also use tools like Recapped.io or Dock.us. Common Closing Strategies: • Summary Close: Reviewing the key benefits and value of the product right before signing. • Urgency Close: Highlighting limited-time offers or implementation timelines (though often less effective; can be viewed as a pressure tactic to close before the prospect is ready). Well-crafted, realistic Engagement Plans greatly improve forecasting accuracy, enhance the probability of closing, and facilitate team coordination, particularly for complex B2B deals.
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David Gersh shared thisIf You Want a CRO Role, You Should Be Able to Answer This If I asked you: “How do you take a company from $20M ARR to a successful exit?” Could you answer clearly? Not in theory. In execution. Because that’s the real CRO job. Not: - Hiring reps - Forecasting pipeline - Managing territories But: 👉 Designing the system that turns growth into enterprise value. That means: - Enterprise expansion - Channel scale - Pricing leverage - Retention economics - Strategic positioning CRO isn’t a sales role. It’s a VALUE CREATION role.
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David Gersh shared thisHow CROs Should Think About Exit-Driven Growth
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David Gersh shared thisWhy Most SaaS Companies Hit a Growth Ceiling (and Don’t Know Why) At ~$10M–$30M ARR, most SaaS companies stall. Not because of product. Not because of market. Because of GTM architecture failure. What got them there: - Founder-led sales - Opportunistic deals - Lightweight process What they need next: - Segmentation (SMB vs MM vs Enterprise) - Real pipeline discipline - Enterprise motion - Channel leverage Without that shift, growth plateaus. With it: 👉 2–3x growth becomes possible. This is the inflection point where companies either: - Scale - Or stall
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David Gersh posted thisCRO OPERATING PHILOSOPHY (PART 2) Most CROs Don’t Actually Build Companies. They Just Hit Numbers. Most revenue leaders are measured on one thing: 👉 Did you hit the number? But boards don’t reward that. They reward: 👉 Enterprise value creation There’s a difference. The best CROs don’t just drive revenue. They build systems that produce: - Predictable growth - Expanding deal sizes - Increasing retention - Strategic positioning Because ultimately, revenue is not the goal; exit value is! That’s how I think about the role: FROM ARR TO EXIT.
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David Gersh posted thisCRO OPERATING PHILOSOPHY Revenue growth is not a sales problem. It’s an architecture problem. Enterprise SaaS companies plateau when revenue becomes personality-driven rather than system-driven. Predictable ARR growth requires: • Defined ICP discipline - If the Ideal Customer Profile (ICP) is vague, pipeline fills with low- probability opportunities that inflate forecasts and destroy productivity. • Capacity-based territory design - Revenue scale is mathematical. - Most organizations assign territories based on geography or history rather than revenue capacity modeling. - That’s engineered leverage. • 3–5x pipeline coverage standards - "Hopium" is not a forecast. - Institutional growth requires enforcing pipeline coverage ratios — not relying on late-stage heroics. - Boards invest in predictability. • Forecast governance cadence - Forecasting is not a spreadsheet exercise. - It’s a leadership system. - A forecast should withstand board scrutiny and investor diligence. • Net Revenue Retention (NRR)-focused expansion architecture - Enterprise SaaS value is built in expansion. - New logo growth is expensive. Expansion revenue compounds. - Implementing structured health checks increases renewal certainty and materially expands upsell revenue within 12 months. • CAC/LTV Balance - Growth without capital efficiency erodes valuation. - Engineering institutional growth means: - Revenue scale must align with valuation math. The role of a modern CRO is not simply closing business. It is engineering institutional growth: • Does not depend on one rainmaker • Does not collapse when leadership changes • Survives board scrutiny • Improves capital efficiency over time • Increases enterprise valuation It transforms revenue from personality-driven performance to system-driven performance. Institutional growth is: - Predictable - Repeatable - Instrumented - Board-ready It replaces heroic sales culture with disciplined operating culture. THE ROLE OF THE MODERN CRO The CRO is not the head salesperson. The CRO is the architect of: - Revenue predictability - Organizational alignment - Capital efficiency - Valuation expansion In high-growth enterprise SaaS, engineering growth is the difference between scaling to $500M ARR and scaling beyond it to $1B+.
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David Gersh shared thisIf you are a professional in New Hampshire with 20+ years of experience and are interested in joining one of the most rapidly growing (1,000+ members) networking organizations in the US, please message me directly to join our March 5th local chapter OpenWater Day event (open to members and those considering membership) or click on either of the links in the Comments section to apply for membership or to register for an online information session. Within my first 30 days, I was able to help another member, plus be helped myself!David Gersh shared thisNext week, OpenWater Group, our free community for experienced professionals with 20+ years under their belt, is doing something we've never done before. On March 5th, chapters across the country will gather simultaneously to celebrate OpenWater Day and our 1,000-member milestone. We have events happening in Seattle (March 4th!), Reston VA, Atlanta, Phoenix, Dallas, New York City, White Plains NY, San Francisco, Menlo Park, San Rafael, Alameda, Los Angeles and Arvada CO (and more to come)! If you've been curious about OpenWater, this is a great way to show up, meet some members, and see what the community is all about in person. No pitch. No agenda. Just good people getting together. Huge thanks to our organizers! Tony Verde, Jenolee Muschette Lindsay, Elizabeth Jenswold, Seth McColley, MBA, Christine Mariotti, Caryl Baron, CPA, Seth Schachner, Sharon Schanzer, Seth Potter, Denise Chaffin, Tom Schurman, Greena George, Lorrianne Nault, Whitney Shinkle, Janine Kubert, Anita Baker, Jonathan Romanowsky, Shannon Fischer, Meralee Inman Fredenburgh, Mike Scafidi, Alan Cohen, Paul Walborsky, Elaine Zhu All the chapter meetup links are in the comments below. Find your city and come join us. 👇
David Gersh commented on a post
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Victor - love how you captured all of the many emotions that come with transition. I remember my early, "exciting" days of business travel - my wife and young children holding onto every last second of their goodbyes, only to be exceeded by their jubilant, life-squeezing hugs at the waiting area upon my return. But I traveled so much that eventually the drop-offs and pick-ups waned and eventually ended altogether. No more "shrieks," as you mentioned. And with every trip alone, every walk through an airport seeing other families going through their own departure-arrival rituals, I felt a cold, deep sadness of having to spend any time apart, but which was also the strongest motivation to succeed when I considered the cost.
David Gersh commented on a post
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Yes, yes, yes! As we start out, we typically don’t know what we want. We head in various directions, influenced by a favorite teacher or a parent or a friend or something that sounds nice or seems to come easy. And before we know it, several years have passed as we pursued some level of satisfaction or happiness or accomplishment. But for those lucky enough or observant enough or self-reflective, there’s a questioning pause, lifting the head up to look around and perhaps notice something else that just might be a better fit now. For those with the means to pivot at that moment, do so! Seize the moment; be true to yourself; choose your personal destiny rather than the comfort of the now-mundane. Invest in yourself with all of your energy regardless whether it truly is your ultimate destination, knowing that, if it isn’t, you can say, “I tried, and will try again!” But if it is, soar with the freedom of realizing you’ve found who you were meant to become and cherish each day.
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David Gersh liked thisDavid Gersh liked thisPitchslaps have officially left the DMs and are now showing up in the connection request. I repeat. THE CONNECTION REQUEST. We haven't met. We haven't spoken. You don't know me. And yet somehow you thought the best first impression was a 400-word pitch about your services shoved into the little note box like a flyer under a windshield wiper. Sir. Ma'am. Bestie. No. If you've ever gotten my auto-reply, you already know how I feel about this. And if you've never heard the term pitchslap, congratulations, it means you haven't done enough research to know that the entire LinkedIn creator universe has been screaming about this for years. There are literally thousands of people telling you exactly how to do this right. They are not hard to find. Would you walk up to a stranger at a networking event, shake their hand, and immediately launch into your sales deck before they've told you their name? No. You would not. Because you would be escorted out. Or at minimum, avoided for the rest of the evening. LinkedIn is not different. It is just slower, and you can't see people's faces when they cringe. Connect like a human. Start a conversation. Be curious about the other person for approximately five seconds before you ask them for something. It's not complicated. It's just manners, good business, and apparently a lost art. Do Better!! #nopitchslaps #leadership #linkedinmanners
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David Gersh liked thisDavid Gersh liked thisA suit doesn't make the man. But the man makes the meaning. I wrote that line thinking about my father. Then I realized it had nothing to do with him. It was about every room I'd walked into already rehearsing my exit. Every conversation I'd led from a version of myself still becoming. The suit was never the problem. The problem was believing I needed to earn the right to wear it. Most leaders I sit with are still waiting for that permission: from the board, from the market, from the voice in their head that's been keeping score since childhood. It never comes from out there. It never did. I help successful people name what they can't see.
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David Gersh liked thisDavid Gersh liked thisI recently departed Coforge after 5+ incredible years. During that time, I built a Partner Ecosystem and Strategic Communications program, celebrated reaching $1B and then $2B in revenue, emceed Coforge's annual Engage and CSG events, and worked under multiple leaders and one CEO. I grew immensely as a professional and learned what it's like to truly love what you do and wake up every day excited to take on the next challenge. Thank you to all the wonderful colleagues I've had the pleasure of working with over the years. I've made friendships that I will take with me. I'm excited for my next challenge, but for now, I'm looking forward to some time at the potters wheel.
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David Gersh liked thisDavid Gersh liked thisA suit does not make a man My father never owned a suit. I only saw him in one once. A hand-painted photograph. Him and my mother. Taken before the unraveling. Before the drinking settled in like weather. Before I understood that the man in the photograph and the man who raised me were not exactly the same person. He was still a kid waiting for Superman. Aren't we all, for a while. The photograph lived on a shelf in between books. I must have passed it a thousand times without really looking. Then one day I looked. And I saw something I hadn't seen before. He was trying. Not performing or posing. Trying. You could see it in the way he held himself. Slightly uncertain, slightly hopeful, dressed in something that wasn't his but wanting to be worthy of it. I recognize that posture now. I've worn it myself. In boardrooms, in conversations, in rooms where I wasn't sure I belonged but showed up anyway, dressed for the version of myself I was still becoming. The suit doesn't make the man. But the man makes the meaning. I'm still taking measures. So are you. The question isn't whether you've arrived. The question is whether you know what you're dressed for. I help successful people name what they can't see.
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David Gersh liked thisDavid Gersh liked thisThis Sunday Morning, a letter about the difference between building a life that works. And building one that feels like yours.
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SPIN Selling
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