Chris Arsenault

Category: The Musings

Long-form writing on technology, leadership, AI strategy, and execution inside complex organizations.

  • The Conference Dinner Playbook

    Some of the highest-ROI BD activity of any conference is the dinner. Not the sponsored dinner — the ones you organize yourself. Done well, a 10-person dinner at a good restaurant during a major conference is worth more than most of the sessions combined.

    Most sellers don’t do this because it seems like a lot of work for an ambiguous return. In practice, it’s the single best thing you can do at any conference with real budget behind it.

    Why Dinners Work

    Conferences produce short, shallow interactions by default. A booth visit is ten minutes. A hallway chat is five. A session-adjacent conversation is tactical at best. None of these create the kind of engagement that produces pipeline, because the bandwidth is too low and the setting is too public.

    A dinner is different. Two hours. Alcohol. A small group. A good restaurant. You get depth of conversation that no other conference setting produces. Relationships deepen in hours that would take months otherwise.

    More importantly: a dinner is an asymmetric gift. You’re hosting. Your guests are receiving. That dynamic — you as host, them as guests — changes the relational register in a way that favors you for the next twelve to eighteen months after the conference.

    The Playbook

    1. Pick the right guests.
    Not “customers and prospects” as a broad category. Eight to twelve specific people you want to build relationships with. Mix of current customers, target prospects, and strategic industry contacts. The mix matters because the conversation across these groups is what produces the most interesting dinners.

    2. Invite early and specifically.
    Reach out four to six weeks before the conference. Personal invitation, not a group email. Reference something specific about them — why you want them at this dinner, not just at any dinner. The personal invitation makes it feel like an honor, not an extraction attempt.

    3. Pick a restaurant with conversation in mind.
    Private room or quiet corner. Not the loudest restaurant in the city. Not the trendiest. The goal is conversation, not impressing guests with the venue. Menu that’s shareable but not too performative. Reasonable wine program without being excessive.

    4. Don’t pitch.
    This is the most important rule. The dinner is not a sales dinner. It’s a relationship dinner. If you spend the evening pitching your product, you’ve lost — your guests will leave feeling they were extracted from. If you spend the evening hosting a conversation where everyone brings something to the table, your guests leave having had a genuinely good time with you, and your product comes up organically or doesn’t come up at all.

    The pipeline comes from the relationship, not from the pitch. Pitch at dinners specifically kills both.

    5. Follow up personally within 48 hours.
    Not “great dinner — let’s stay in touch.” Specific: reference something they said, connect them with someone you mentioned during dinner, send them the article that came up. The follow-up extends the dinner into ongoing contact.

    The Economics

    A 10-person dinner in a major city runs $2,000 to $4,000 with wine. Compare that to the cost of acquiring pipeline through paid marketing, SDR outbound, or the expected value of conference booth presence. The dinner, done well, generates more relational depth and pipeline potential than any of those.

    The reason more sellers don’t do this is that it’s effortful in ways other activities aren’t. You have to plan. You have to curate. You have to host. You can’t automate it. You can’t outsource it. You have to actually be good company for two hours in front of ten people who are watching how you behave.

    But for sellers who can do this well, the return is disproportionate. One well-hosted dinner per major conference can be the highest-leverage hour you invest in any given quarter.

    Book the dinner. Invite carefully. Don’t pitch. Follow up personally.

    That’s the playbook. Most sellers won’t do it. Which is why the ones who do pull away.

  • Why Your Deal Died in Procurement

    “We’ve hit a snag in procurement” is one of the most common phrases a seller hears late in a deal cycle. By the time it’s said, the deal is usually already in trouble, and the trouble almost always has the same structural cause.

    Most deals that die in procurement were dying earlier — sellers just didn’t recognize the signals, and procurement became the visible cause of a decision that had already been made upstream.

    The Pattern

    Procurement rarely kills deals on its own merits. What procurement does is surface the underlying weaknesses in the deal and force them into visibility at a time when the seller has the least leverage to address them.

    If your champion hasn’t fully convinced the economic buyer, procurement will find the gap. If the ROI case hasn’t been made rigorously, procurement will push back on pricing. If the business urgency hasn’t been established, procurement will slow the timeline until the urgency evaporates.

    In all of these scenarios, procurement is doing its job — protecting the company from bad vendor decisions. What looks like “procurement killing the deal” is really procurement revealing the deal was weaker than you thought.

    The Signals You Missed

    Several upstream signals predict procurement problems:

    1. Your champion couldn’t articulate the cost of not buying.
    If the champion can’t clearly explain what breaks if the company doesn’t make the purchase, procurement’s questions about ROI will expose the gap. The champion may be enthusiastic but unable to defend the investment when challenged. Procurement will find this out in month three and push back accordingly.

    2. The economic buyer never engaged directly.
    If you’ve been selling primarily to your champion, and the economic buyer has only been copied on emails, procurement often becomes the mechanism by which the economic buyer’s unspoken reservations surface. The economic buyer wasn’t going to say no directly, but they don’t need to — procurement will do it for them.

    3. The timeline was optimistic.
    If your deal timeline didn’t include adequate time for procurement, legal, and finance review, those functions will slow the deal to match their actual process. What looks like “procurement dragging their feet” is often procurement operating at their normal pace while your seller-driven timeline was unrealistic.

    4. The pricing wasn’t defensible to an outsider.
    If your pricing relied on your champion accepting it on faith, procurement will force a defense of the pricing with specifics. If the specifics don’t hold up, procurement will extract discounts — not because they’re aggressive, but because the pricing wasn’t grounded in defensible logic.

    How to Prevent the Procurement Death Spiral

    Three moves early in the cycle that prevent most procurement problems:

    1. Engage procurement early.
    Not at the end, when they’re surprised by the deal. Early, when you can shape their perception. Even a courtesy call in week two — “I know you’ll eventually need to review this, and I wanted to make sure you understood what we’re discussing and when it will likely come to you” — pays compound returns later.

    2. Help your champion build the ROI case themselves.
    Don’t write it for them. Walk through the logic together so they own it. A champion who built their own ROI case can defend it to procurement, the CFO, and the board. A champion who was handed the case can’t.

    3. Price with defensible specifics.
    Every pricing element should have a rationale your champion can explain. If the implementation is $X, it’s because Y specific work is required. If the annual is $Z, it’s because the ROI math supports that value. Pricing without defensible logic invites procurement to reduce it.

    Procurement doesn’t kill healthy deals. It surfaces the weaknesses in unhealthy ones.

    If you’re losing deals in procurement, the fix is rarely “better procurement engagement at the end.” The fix is stronger upstream selling — clearer ROI, earlier economic buyer engagement, realistic timelines, defensible pricing.

    Fix the upstream. Procurement becomes a milestone, not a mortality event.

  • The Quiet Year: Why Relationship Investment Looks Unproductive in Year One

    If you start seriously investing in your network today — more intentional introductions, more consistent cadence, more generous presence — you probably won’t see measurable returns for a year or more. This disconnect between input and output is why most professionals don’t make the investment, and why the ones who do end up with permanent structural advantages.

    Relationship investment has a ramp profile that feels unproductive in the short term and compounds unexpectedly in the medium and long term. Understanding the profile is the difference between sticking with the investment long enough to benefit from it and giving up before it starts working.

    The First Six Months: Investment Without Return

    You start reaching out more. Making introductions. Writing notes. Offering help without expectation.

    For the first six months, almost nothing comes back. The network knows you less as a giver than as someone who occasionally participates. Your new cadence is registering, but it hasn’t yet changed how people think about you. Referrals don’t increase. Inbound stays flat. The pipeline is unchanged.

    This is the period where most people quit the investment. It feels like work without reward. The spreadsheet showing you’ve done “30 introductions this quarter” feels like activity, not productivity.

    The data isn’t in yet. Be patient.

    Months 6-12: The First Signals

    Somewhere between month six and month twelve, small things start happening. Someone mentions you favorably in a conversation you weren’t in. You get an unusual introduction from someone you’d helped earlier. A relationship that had been dormant resurfaces because you’d stayed warmly present.

    These signals are small and attribution is fuzzy. You can’t prove they’re downstream of your investment. But they start showing up, and the rate slowly increases.

    The internal experience of this phase is strange: you’re still doing the work without clear proof it’s working, but the ambient temperature of your network feels different. People are slightly warmer. Conversations slightly easier. Access slightly wider. You can’t put your finger on it.

    Months 12-24: The Compounding Begins

    This is when the investment starts visibly paying. Not dramatically — compounding is quiet — but noticeably.

    Inbound opportunities increase. Not from any specific person — from the network as a whole. Referrals become more common. Conversations that previously would have required pursuit now come to you. People you’ve never met reach out because “someone mentioned I should talk to you.”

    By month 24, if you’ve maintained the investment, you’re operating in a different regime than you were at month zero. Not because you’ve learned new tactics, but because the network has changed its collective stance toward you.

    Why Most People Don’t Wait

    The 24-month ramp is longer than most operators will patiently invest against. The short-term ROI is invisible. The short-term cost is real — hours per week on activity that doesn’t produce measurable results.

    Most people quit around month six. They conclude networking “doesn’t work for them” and go back to transactional behavior. Their version of the experiment was accurate in its first six months — nothing came back — but incomplete. They never saw the compounding phase because they didn’t stay long enough.

    The operators who make it through the quiet year do so because they’re either temperamentally patient, or because someone 10 years ahead of them has explained that this is how the ramp works and they should stick with it.

    The Bet You’re Making

    Investing in the quiet year is a bet that:

    • Future opportunities will be disproportionately referred rather than pursued
    • The relationships you deposit into will eventually produce returns
    • The compounding is real even when it’s invisible

    If those bets prove right — and in my experience, they do — the quiet year pays for years afterward. If they prove wrong, you’ve spent some hours being generous without specific returns. That’s also a fine outcome.

    The quiet year is where most professionals either build the foundation of their career or fail to. The activity is unglamorous. The payoff is delayed. The cost is real.

    Pay it anyway. On a 20-year horizon, it’s one of the best investments available.

  • The Content That Actually Converts

    Most B2B content is produced by committee, optimized for SEO or social engagement, and converts at rates close to zero. The content that actually drives pipeline is typically produced by a small number of people, optimized for specific reader insight, and converts at rates orders of magnitude higher.

    Understanding the delta — why one produces pipeline and the other doesn’t — is the difference between content being a cost center and a revenue channel.

    The Pattern of Content That Doesn’t Convert

    It’s written for “personas” rather than people.
    Persona-driven content is generic by construction. It’s written for “the VP of Operations at a mid-market company” — which means it’s written for nobody. The VP of Operations at a specific mid-market company has specific problems, specific language, specific constraints. Persona content captures none of that.

    It competes on SEO rather than on insight.
    SEO-optimized content is optimized to be found, not to be read. When the reader arrives, the content is usually thin — produced to hit keyword density, word count, and structural SEO elements. It ranks. It doesn’t convert.

    It’s signal-free.
    The reader can’t tell whether the author actually has expertise, experience, or a point of view. Content without an explicit point of view feels like it could have been written by anyone (and increasingly, by AI). The reader nods, closes the tab, and doesn’t associate anything specific with the author or the company.

    The Pattern of Content That Does Convert

    It’s written for specific people facing specific problems.
    Not personas — actual scenarios. “The operations leader whose team has been asked to absorb 20% more volume with the same headcount and who can’t figure out what to cut without breaking something else.” That level of specificity makes the right reader feel seen. The wrong reader bounces, which is also correct.

    It has an opinion.
    Content that converts is content that takes a position. “Here’s what I think is happening, here’s what I think is wrong about how most people approach it, here’s what I recommend.” Opinions polarize. The readers who disagree leave. The readers who agree become candidates for further engagement.

    It’s signed by someone with credibility.
    The author’s background is visible and relevant. Not “written by marketing.” Written by a specific person whose experience gives the opinion weight. The byline matters because trust matters.

    What Converts in 2026

    Specifically, in the current content environment, three formats consistently convert pipeline:

    1. Founder-written insight pieces.
    1,000 to 2,000 word pieces on specific patterns the founder has observed, written in their voice, with specific recommendations. These read as thought leadership, not as marketing. They work because the voice is genuine and the perspective is earned.

    2. Customer case studies written as narrative.
    Not the sanitized “challenge/solution/results” format. Actual narrative — what the customer tried first, what didn’t work, what the specific mechanism was that got them unstuck. Narrative case studies convert at multiples of template case studies.

    3. Contrarian analysis of industry conventional wisdom.
    “Here’s what most companies do about X. Here’s why it usually doesn’t work. Here’s what I’ve seen work instead.” These pieces get shared because they give the reader ammunition to push back on their own company’s default patterns.

    What to Stop Producing

    If it’s any of these, consider stopping:

    • Generic top-of-funnel “ultimate guides” optimized for SEO
    • Persona-addressed blog posts that could be about any company
    • AI-generated content that has no human fingerprint
    • Content calendars designed to hit a volume target rather than to produce insight

    The time and money saved from not producing this content can be redirected to producing less content of higher quality. The math works out dramatically in favor of the second approach.

    Content converts when it’s specific, opinionated, and signed by someone credible. Everything else is noise.

    The companies that figure this out early build content programs that produce pipeline at economics competitors can’t match. The ones that don’t keep investing in volume and wonder why the dashboard looks flat.

    Pick your side.

  • Co-Marketing Without Co-Selling

    Many partnerships are called “partnerships” but are really co-marketing arrangements. Press releases, joint webinars, logo exchange, shared content — these are marketing collaborations that don’t require the operational complexity of true co-selling.

    Recognizing this distinction — and being honest about which you’re in — saves both sides from building expectations the relationship can’t support.

    What Co-Marketing Actually Is

    Co-marketing is two companies using each other’s audiences or credibility to reach customers. It doesn’t require revenue integration, joint selling, or shared pipeline. Both companies benefit from association with the other, each gets some marketing leverage, and the collaboration can be low-friction.

    Examples: co-hosted webinar where both companies present, joint blog content, shared customer event sponsorship, case study featuring both products, co-branded research reports.

    None of these require operational integration. Both sides can cancel with 30 days’ notice. The risk is low, the upside is modest but real.

    What Co-Marketing Is Not

    Co-marketing is not a replacement for co-selling. Revenue partnerships — where two companies actually sell together and share deal economics — are operationally intensive and structurally different. They require aligned comp plans, joint pipeline reviews, dedicated operators, and real commercial commitments.

    The confusion happens when companies call co-marketing a “strategic partnership” and then get frustrated when revenue doesn’t materialize. The co-marketing was working fine — it was just never going to drive revenue on its own, because that’s not what co-marketing does.

    When to Use Each

    Use co-marketing when:
    – You want market exposure with low operational cost
    – The other company has an audience that aligns with yours
    – You don’t have the capacity for a real co-sell motion
    – You want to test the relationship before committing more
    – Revenue isn’t the primary goal (brand, credibility, thought leadership are)

    Use co-selling when:
    – Both companies have aligned incentives for joint revenue
    – There’s a specific joint offering that neither company can deliver alone
    – You have dedicated operators on both sides
    – You’re prepared for the operational cadence real co-selling requires
    – You’re willing to invest in the structural commitments (kill criteria, joint plans, shared comp)

    The mistake is using co-marketing as a substitute for co-selling and expecting co-selling results. The co-marketing works; the expectation was miscalibrated.

    How to Structure Co-Marketing Well

    Even low-friction co-marketing benefits from a few structural commitments:

    1. Named goals.
    “We’ll run a joint webinar” is activity. “We’ll run a joint webinar aimed at producing 200 registrations from our combined audience, with 20% expected conversion to follow-up” is a goal. Goals make it easy to assess whether the collaboration is working.

    2. Equitable contribution.
    Co-marketing works when both sides contribute roughly equally — audience, content, promotion. Lopsided arrangements decay because the side contributing more notices the imbalance.

    3. Time-bounded scope.
    Co-marketing works best in discrete projects — a webinar, a report, an event. Open-ended co-marketing drifts because nobody’s managing the ongoing commitment. Define the specific project, deliver it, assess, then decide whether to do another.

    4. Honest naming.
    Call it co-marketing. Don’t call it a strategic partnership. The clarity keeps expectations calibrated and lets both sides enjoy the collaboration for what it is.

    Most “partnerships” are actually co-marketing. That’s fine — co-marketing is a legitimate, useful form of collaboration. It’s just not the same as revenue partnership, and treating it as such creates disappointment on both sides.

    If you have a co-marketing relationship, name it accurately and structure it well. If you need revenue partnership, invest in the operational complexity that actually requires.

    Don’t confuse the two. Both suffer when you do.

  • When to Say No to a Round

    Most founder advice is about how to raise money. Less discussed is when to decline it — which, for certain founders at certain stages, is one of the most consequential decisions they’ll make.

    I’ve watched founders take money they didn’t need and regret it. I’ve watched founders decline money that would have accelerated them, and also regret it. Sorting when to say yes and when to say no isn’t a universal formula, but there are patterns that consistently separate the good calls from the bad.

    When Saying Yes Is Clearly Right

    For most early-stage companies, in most environments, taking capital at reasonable terms is the right call. The math is unambiguous: additional runway reduces risk, additional investment enables hiring, additional capital buys market position. When capital is available on fair terms and the company has a clear use for it, decline is usually wrong.

    The founders I’ve watched regret saying no were almost always the ones who said no for emotional reasons — dilution aversion, ego about independence, or unwarranted confidence that the next round would be easier. The market, famously, does not care about emotional reasons.

    When Saying No Is Worth Considering

    Several scenarios where declining capital is genuinely worth considering:

    1. The company doesn’t have a clear use for the money.
    If you can’t articulate specifically what the next $X will be spent on, you probably shouldn’t raise it. Capital without a plan sits on the balance sheet and then gets spent on things that seemed reasonable at the time. Those things are rarely the things that actually drive growth. Capital without clarity is expensive, because you pay dilution for it without getting the growth acceleration it should have bought.

    2. The terms are misaligned with the company’s actual stage.
    Sometimes the market offers capital at terms that imply a growth profile the company doesn’t have. The valuation is higher than the traction justifies. The expected growth rate is more aggressive than the motion can support. Taking this capital creates a valuation overhang that’s difficult to grow into, and the next round gets harder because you’ve already been priced ahead of reality.

    3. The investor-founder fit is wrong.
    Capital comes with investors. Investors come with opinions, board dynamics, expectations, and often specific theories about how the company should be run. If the investor’s theory doesn’t match the founder’s, taking the capital is accepting conflict. Sometimes that’s fine. Sometimes it’s the kind of conflict that burns out the founder within 18 months.

    4. The company is profitable or approaching it.
    Companies that can grow without new capital have leverage most companies don’t. If you’re profitable and growing, the question shifts from “do I need capital?” to “does capital accelerate my specific motion?” Sometimes yes. Sometimes the acceleration is marginal and the dilution is real.

    The Question I’ve Heard Used Well

    Founders I’ve worked with who’ve made thoughtful capital decisions have a version of this question they ask themselves: if I take this capital, what specifically changes in the next 18 months that wouldn’t have changed without it?

    If the answer is “we grow faster” without specifics, the case is weak. If the answer is “we hire three specific roles that unlock a specific growth motion we can’t currently run” — the case is strong.

    The Meta-Lesson

    The founders I’ve watched navigate capital decisions most gracefully treated funding as a tool, not as validation. They raised when they had a clear use, declined when they didn’t, and weren’t emotionally attached to any specific round as a marker of their company’s worth.

    The founders who struggled with capital decisions were the ones who treated each round as a judgment of the company. Taking capital became a signal that the company was legitimate. Declining capital felt like admitting weakness. Neither framing serves the actual decision.

    Capital is an input, not an outcome. Sometimes the right move is to take it. Sometimes the right move is to wait. Knowing which is which requires thinking about capital as a tool rather than as a scoreboard.

    Many of the best companies I’ve watched build had at least one round they declined and didn’t regret.

  • The Three Calls That Matter in a Deal

    Every enterprise deal I’ve seen close had three specific calls that disproportionately determined the outcome. Not the first call, not the demo, not the closing call — those matter, but they’re not the ones that decide.

    The three that decide are: the honest discovery call, the stakeholder alignment call, and the late-stage pressure call. Most sellers recognize them only in retrospect. The ones who identify them in real time and prepare for them with the weight they deserve close at materially higher rates.

    The Honest Discovery Call

    This is not the first discovery call. It’s the second or third — the one where the customer stops performing politeness and starts talking honestly about what’s actually going on.

    The first discovery call is usually somewhat surface. The customer is feeling you out. They’re answering the questions you ask, but they’re staying within what they’ve told other vendors, not going deeper.

    The honest discovery call happens when the customer has decided you might actually be useful. They shift from answering questions to asking for your perspective. They share a problem they haven’t shared before. They let you into something they wouldn’t let a generic vendor into.

    The tell: when the customer starts saying “what I haven’t told other vendors is…” or “honestly, the real problem here is…” — that’s the shift.

    Your job in this call is to listen, ask sharper questions, and deliver a piece of perspective that demonstrates you’ve earned the honesty. Get this call right and the deal moves. Miss it and you’re still in first-date mode for the rest of the cycle.

    The Stakeholder Alignment Call

    Every enterprise deal has a moment where the deal either aligns across the buying committee or it doesn’t. This is rarely the first time you meet the buying committee — it’s the meeting where they’ve stopped evaluating individually and start evaluating collectively.

    You can feel it coming. One stakeholder says “let me bring in Maria.” Another says “I need to walk this through our architecture team.” The deal is consolidating — multiple stakeholders are now trying to agree on the same answer.

    Your job in the alignment call is structural, not persuasive. Make sure the right people are in the room. Make sure the conversation addresses each stakeholder’s specific concern. Don’t push toward a conclusion — make space for the group to reach one.

    Deals that align in this meeting close. Deals that don’t, don’t. The delta is rarely about product. It’s about whether the meeting is structured to let alignment emerge.

    The Late-Stage Pressure Call

    Somewhere in the last 20% of the deal, something goes wrong. Procurement pushes back harder than expected. Legal surfaces a concern. A competitor re-enters the conversation. The deal stalls or threatens to.

    This call — the one where you address the late-stage pressure — is where most deals are won or lost. Not because the pressure is decisive on its own, but because how you handle it reveals what kind of vendor you are.

    Sellers who panic, discount aggressively, or over-promise to resolve the pressure lose credibility. Sellers who calmly restate the value, negotiate firmly on terms, and resolve the specific concern without destabilizing the deal preserve credibility.

    The customer is watching how you handle pressure because it tells them how you’ll handle pressure post-close. If you buckle under pre-close pressure, you’ll buckle post-close. If you hold the line now, they can trust you later.

    Three calls. One early, one middle, one late. Most sellers prepare disproportionately for the first meeting and the closing call. The sellers who win disproportionately prepare for these three.

    Know which call you’re in when you’re in it. Prepare accordingly. Everything else in the deal is supporting choreography.

  • Why Most Demo Calls Are Broken

    Most software and technology demos are designed to show off the product. The buyer’s perspective — what they actually need to understand, what decisions they’re trying to make, what risks they’re trying to assess — is usually an afterthought. The result is a demo that’s impressive to the product team and mostly useless to the buyer.

    Better demos are constructed around three principles that most sales teams either miss or ignore.

    Principle 1: The Demo Is Not the Selling

    The demo is where the buyer confirms what they already believed. Selling happens in discovery, in the narrative you build, in the relationships. By the time you’re demoing, the buyer has usually made a preliminary decision based on what they understood about your company before the demo. The demo either confirms or disconfirms that preliminary decision.

    This means the demo’s job is not to create desire. Desire was (or wasn’t) created earlier. The demo’s job is to remove doubt. Every minute of the demo should be serving a specific doubt the buyer has already surfaced — either in discovery or in their own head.

    A demo that tries to create desire usually fails. The buyer sees features they don’t need, workflows they won’t use, dashboards that don’t address their actual problem. The pitch feels generic because it is. You’re showing them a tour of the product, not an answer to their question.

    Principle 2: The Questions Drive the Demo, Not the Script

    The best demos I’ve watched started with the seller asking, “Before I show you anything, what are the three things you specifically want to see today?” And then the demo was structured around those three things.

    The worst demos I’ve watched were the ones where the product marketing script was executed beat-by-beat regardless of what the buyer cared about. The script covered the full product. The buyer wanted to see one workflow. The buyer spent 40 minutes waiting for the relevant part.

    Scripted demos signal that the seller isn’t listening. Listening demos signal that the seller is there to help the buyer evaluate, not to perform.

    Principle 3: Show the Ugly Parts

    Most demos show only the smooth happy path. “Here’s how it works.” Click. Click. Click. Perfect.

    The buyer knows no software is that smooth. What they’re actually trying to understand is: where does it struggle? What happens when I try something complicated? How does it handle my weird edge case?

    Demos that show the ugly parts — “here’s where it gets tricky, and here’s how we handle it” — build trust faster than demos that don’t. The ugly parts aren’t embarrassing; they’re what makes the rest of the demo credible.

    When I’m buying, the vendor that walked me through the hard cases was the vendor I trusted. The vendor that showed me only the clean version was the vendor I mentally discounted, because I knew they were hiding something and I didn’t know what.

    The Structural Move

    Before your next demo, call the buyer. Fifteen minutes. Ask: “What do you specifically want to understand from this demo? What are the questions that, if I answer them well today, make this an easy decision? What would someone on your team push back on, and what do you need to see to address that pushback?”

    Structure the demo around those answers. Skip the rest.

    The demos that close are the ones that answer the buyer’s questions. The demos that don’t close are the ones that perform the product tour.

    Stop running tour demos. Start running question-answering demos. Your close rate will tell you which one was the problem.

  • The Cadence of Showing Up

    The relationships that compound are the ones where you show up consistently, not the ones where you show up intensely. This is obvious stated that way, and harder to implement than it sounds, because intensity is easier to muster than cadence.

    In my career, the most durable relationships have been built on small, regular contact over years. A quarterly check-in. A note when I saw something relevant to them. An introduction, unprompted, when I thought two people should know each other. None of it individually consequential. Cumulatively, the foundation of most of the opportunities I’ve had for the last two decades.

    The relationships that haven’t lasted — and I’ve had many — were the ones where I brought intensity in short bursts. Deep engagement during a specific project. Genuine interest for the duration of one deal. Then silence, when the immediate context was gone.

    Intensity without cadence doesn’t compound. Cadence without intensity is fine. Cadence with occasional intensity is the target.

    The Cadence I Try to Maintain

    Top 20 relationships: quarterly touch.
    Not every one every quarter — but over a year, every one gets contacted at least three times. Usually a note, sometimes a call, occasionally a coffee. The specific cadence matters less than the fact that it’s regular and reliable.

    Top 50 relationships: twice-a-year touch.
    A wider circle where the context is lighter but the connection is kept warm. Usually this is a relevant article, an introduction, or a congratulatory note when I see them announce something.

    Top 150 relationships: annually or when specifically relevant.
    The broader network. Not in active contact, but close enough that a purposeful note — responding to their work, congratulating a milestone, offering help on something I know they care about — keeps the relationship alive.

    The Mechanics

    1. Write it down.
    The relationships I can keep in my head are not the relationships I reliably maintain. The ones I track in a simple spreadsheet — last contact date, topic, direction of the relationship — are the ones that stay warm. Memory is not a system. A list is a system.

    2. Batch the work.
    I have a regular Sunday evening block for relationship hygiene. Not long — maybe 30 to 60 minutes. Sometimes I send three notes. Sometimes I send ten. The block exists regardless of how busy the week has been. The block is the commitment.

    3. Deliver value in every touch.
    The touch that doesn’t deliver something useful is a burden on the relationship, not a deposit. Every note has to have a reason for the recipient to value receiving it. Article. Introduction. Perspective. Congratulation. Question they can help with. Without the value, the touch is just an ask for attention, and those accumulate as a negative.

    4. Let some relationships rest.
    Not every relationship needs to stay active. Some have completed their arc. Some are dormant for reasons that will resolve later. Trying to maintain everything produces a motion that’s performative — you end up sending notes for the sake of sending notes, and the recipients feel it.

    The relationships that compound are the ones where cadence and intentional investment meet. Consistency over intensity. Value over volume. Genuine interest over scheduled contact.

    Over a decade, that approach produces a network the rest of your career rests on. Without it, you spend middle career rebuilding what you thought you had built in early career.

    Show up regularly. Small notes. Valuable context. Enough years to compound.

    That’s the whole practice.

  • The Founder’s Customer Advisory Board

    A Customer Advisory Board, done well, is one of the highest-leverage activities a founder can run in the early and growth stages of a company. Done poorly, it’s a quarterly meeting that makes executives feel important and produces nothing. The difference is in how it’s structured — and most founders get the structure wrong.

    What a CAB Actually Is

    A CAB is a structured, ongoing forum where a small group of your most strategically important customers — usually 8 to 12 — provide direct input on your product direction, go-to-market positioning, and strategic choices.

    It’s not a user group. It’s not a quarterly review. It’s not a thinly disguised marketing event. A CAB that does any of those things is either underperforming or being used for the wrong purpose.

    Why Founders Should Run Them

    Three strategic benefits that compound over time:

    1. Product feedback from the customers whose feedback matters most.
    Not all customers are equally useful for product feedback. Your top customers — the ones you’re building for, the ones who represent the market you want to own — give you input that shapes roadmap in ways that general user feedback can’t. A well-run CAB surfaces what these customers need before it shows up in lost deals.

    2. Relationship deepening with strategic accounts.
    Being on a CAB is an implicit signal of commitment. Customers who join a CAB are telling you they’re invested in your company’s direction. That relationship is stronger than any quarterly business review can produce. Expansion revenue from CAB members is consistently disproportionate to their share of the customer base.

    3. Strategic pressure-testing.
    Founders who present their strategy to smart operators every 90 days get challenged in ways they don’t get internally. Board members offer strategic oversight. Employees offer execution input. Customers offer reality-testing on whether the strategy actually maps to their situation. That voice is hard to get from anywhere else.

    How to Structure One

    1. Pick the right members.
    Not your biggest customers. Not your loudest customers. Your most strategically representative customers — the ones who represent where you want the company to go. Aim for 8 to 12. Include a mix of vertical/segment representation. Skew slightly toward customers you want to spend more time with, not necessarily the ones who’ve been with you longest.

    2. Meet in person, quarterly.
    Virtual CABs underperform dramatically. The side conversations at dinner are often where the most valuable input happens. The cost of in-person is real, but the output differential justifies it. Two full days, four times a year, in a mix of locations.

    3. Have a specific agenda per meeting.
    Not “let’s hear what’s on your mind.” A structured agenda: one strategic question the founder is wrestling with, one product roadmap review, one GTM challenge, one free-form discussion. Members should receive the agenda a week in advance with pre-read materials.

    4. Capture and follow up.
    Every meeting produces specific action items. The founder sends a recap within a week noting which inputs shaped which decisions. CAB members who feel their input is visibly used engage more. Members who feel ignored disengage. The follow-up is where most CABs fail.

    What Not to Do

    Don’t use the CAB for marketing.
    Case studies, references, PR — these should be separate. Mixing them into CAB meetings makes the members feel used. They’re there to help you think, not to produce marketing assets.

    Don’t over-prepare the content.
    A polished pitch-deck-style presentation signals “we’re performing for you.” Rougher, honest work-in-progress material signals “we want your real input.” The second produces better discussion.

    Don’t let the group become homogeneous.
    If every member represents the same segment, you’re getting the same perspective replayed. Diversity across vertical, company size, and maturity stage produces sharper input.

    When to Start One

    The usual rule I’d offer: a CAB makes sense when you have at least six customers who would each be strategically valuable to have in one room, and when you have strategic questions worth putting to them. Usually somewhere between $2M and $10M ARR for B2B companies, though earlier stage CABs can work for smaller, more intimate formats.

    If you’re earlier than that, you probably don’t need a formal CAB yet. Informal one-on-one founder-to-customer conversations are more valuable at that scale. The CAB becomes valuable when you’ve got enough strategic customers that a group dynamic produces insight the individual conversations don’t.

    A well-run CAB is one of the highest-trust, highest-signal activities a founder can run. The customers get direct access to strategic decisions. The founder gets pressure-tested thinking. The company gets a forum for the conversations that matter most, with the people whose views matter most.

    The reason more founders don’t run them is that they’re work. Recruiting the right members, running quarterly sessions well, capturing and acting on the input — all of it requires executive time that usually feels scarce.

    The math on that tradeoff almost always favors running the CAB. Founders who invest the time build differentiated insight into their market. Founders who don’t lose it to whatever’s louder on any given week.