Chris Arsenault

Category: The Musings

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

  • Your First Sales Hire

    Most founders hire their first salesperson too early, hire the wrong profile, and then blame the hire when it doesn’t work. The pattern is so consistent across the founders I’ve watched and advised that I now treat it as almost inevitable unless the founder actively resists it.

    Here’s the pattern, and here’s how to not repeat it.

    Too Early

    The “too early” failure looks like this: founder is tired of selling. They’ve closed fifteen customers personally. They’ve hit maybe $500K ARR. They’re burning out on the seller role. They hire a VP of Sales or a senior AE to “take it off their plate.”

    Six months later, the rep hasn’t closed anything meaningful. The founder concludes the rep is weak. They let the rep go. They hire another one. Same result.

    The problem wasn’t the rep. The problem was that the sales motion wasn’t repeatable yet. The founder closed fifteen customers by being the founder — the pitch was different every time, the objections were handled through product adjustments, the deal terms varied. There was no playbook for the rep to execute against because the founder was running an R&D operation disguised as a sales motion.

    The rule I’d offer: don’t hire your first real seller until you can describe, in writing, what they’re supposed to do on a typical day. If you can’t describe the motion, you don’t have a motion. You have a series of one-off founder sales.

    Wrong Profile

    The “wrong profile” failure looks like this: founder hires an experienced enterprise AE from a name-brand company. The AE is accomplished, polished, and expensive. They were great at their last company.

    Their last company had a mature playbook, brand recognition, a marketing team generating leads, an SE team supporting deals, and a deal desk structuring pricing. Your company has none of that.

    The AE can’t generate their own pipeline. They don’t know how to sell without support. They’re used to closing inbound deals, not creating demand from scratch. Three quarters in, no revenue.

    The profile you need for your first seller is not a closer from a mature company. It’s a hunter with the temperament and skills of a founder — someone who can prospect, position, handle objections, and close without any of the scaffolding your later-stage sellers will have.

    This profile exists. It’s rare. It almost always costs less than the polished enterprise AE — but is worth more by a wide margin.

    What to Look For

    The best first-sales-hires I’ve watched share a specific set of traits:

    • Comfort with ambiguity. The motion will change every quarter for the first two years. Sellers who need a stable process will be miserable.
    • Willingness to prospect. Cold outreach, network activation, conference work. If the first hire won’t generate their own pipeline, you’ve just hired an expensive order-taker.
    • Product curiosity. They want to understand the product as well as you do, because early-stage sellers are half-product-manager. Sellers who treat product as “not my job” fail early-stage.
    • Track record at a similar stage. Closing at Series A is a different job than closing at Series D. Past success at a similar stage predicts future success. Past success at a later stage predicts almost nothing.

    How to Structure the First Year

    Two moves that separate founders who succeed at this transition from those who don’t:

    1. Keep selling alongside them for the first six months.
    Don’t hand off cold. Run joint deals. Show them the pitch, the objection handling, the deal structures. Treat the first six months as apprenticeship. Founders who disengage too early are the ones who end up firing their first hire — because they taught them nothing before expecting them to perform.

    2. Define the first year outcome in terms of motion, not revenue.
    The goal of year one isn’t to hit quota. The goal is to build a motion the rep can teach to the next rep. If the first rep leaves after eighteen months having closed $500K but leaving no playbook, that’s a failure. If they close $300K and leave a replicable motion, that’s a success.

    Most founders’ first sales hire doesn’t work. The ones that do work are the ones where the founder hired late, hired for the right profile, and invested in the apprenticeship.

    Everything else is expensive learning. And the learning is almost always the founder’s, not the rep’s — the rep just absorbs the blame.

    Be the founder who writes the playbook before hiring the reader.

  • Co-Selling Is a Contact Sport

    “Let’s co-sell” is one of the most common and most meaningless phrases in partnership management. Everyone agrees. Nobody actually does it. The co-sell motion exists in press releases and dies in execution.

    The partnerships that actually drive revenue through joint selling treat it like a contact sport — specific, operational, and grounded in weekly activity rather than strategic theory.

    What Co-Selling Actually Requires

    Real co-selling is not: “send me some leads.” It’s not: “mention us to your customers.” It’s not: “we’ll refer business to each other.”

    Real co-selling is:

    • Joint call planning. Before a customer meeting, both teams meet to agree on objectives, roles, and follow-up.
    • Shared deal reviews. Both teams review joint pipeline weekly or biweekly, with specific ownership on each deal.
    • Integrated account plans. For key joint accounts, the two companies have one combined account plan, not two parallel ones.
    • Coordinated messaging. Both companies’ reps can speak to the combined value proposition, not just their own product.
    • Shared compensation structure. Both sides’ reps are comped on joint deals in a way that incentivizes the motion.

    When all five are in place, co-selling can drive meaningful revenue. When any are missing, co-selling exists in intent but not in practice.

    What I’ve Seen Go Wrong

    The failure mode I’ve watched most often: Company A’s rep brings Company B’s rep into a deal, expects Company B’s rep to show up prepared, and discovers mid-meeting that Company B’s rep doesn’t know the account, hasn’t reviewed the context, and is winging it. The customer notices. The joint motion loses credibility in that account forever.

    Or the reverse: Company B’s rep has been working an account for months. Company A’s rep gets invited in for a specific expertise conversation. Company A’s rep pitches their full product line, stepping on Company B’s positioning. The customer is confused. The partnership gets quietly deprioritized.

    Or the most common: both reps agree to “stay in touch” on a joint opportunity. Neither has a specific next step. Neither has accountability. The opportunity stalls. Neither rep surfaces it in their own pipeline review because the attribution isn’t clear. The deal dies from neglect.

    The pattern across all three: no operational discipline. Good intent, no execution structure.

    The Three Operational Commitments

    Co-sell motions that actually work have three non-negotiables:

    1. Joint call prep.
    Fifteen minutes before any joint customer meeting, both reps are on a call to confirm objectives, roles, who leads what section, and specific handoff language. Not optional. If either rep shows up to the customer meeting without the prep call, the joint motion is not real.

    2. Weekly joint pipeline.
    A recurring, short meeting between the partnership operators at both companies where joint deals are walked account by account. Status, blockers, next actions, owner. If the meeting gets skipped for three weeks in a row, the partnership is dying — regardless of what the executive sponsor says.

    3. Attribution that both sides trust.
    Both companies’ compensation systems track joint deals accurately. If one side is consistently getting credit and the other isn’t, or if the attribution gets argued deal by deal, the reps on the under-credited side stop working the motion. Trust in the attribution math is foundational.

    Where to Start

    If you have a partnership that isn’t driving revenue but should be, start here:

    • Pick three target accounts you’d both want to win jointly.
    • For each, build one joint account plan that both sides commit to.
    • Run weekly 30-minute joint reviews on just those three accounts for one quarter.
    • At quarter end, honestly assess: did the joint motion produce results the individual motions couldn’t have?

    If yes, expand. If no, you have data about whether the partnership is real.

    The co-sell partnerships I’ve watched deliver revenue have always had a specific name on both sides whose job — whose compensated day job — was making it work. Every one that didn’t deliver had “partnership” on a lot of titles and in nobody’s actual job description.

    Name the operator. Run the cadence. Track the attribution. That’s the motion.

    Everything else is theater.

  • The Channel Partner Conflict: Why Most Channel Programs Die

    Every company that sells through channel partners eventually runs into the same structural problem: direct sales and channel sales compete for the same deals. Managing that conflict poorly kills the channel motion. Managing it well turns channel into a real revenue contributor.

    Most companies manage it poorly.

    The Conflict, Named

    Channel partners exist because they have reach, relationships, or scale that the direct sales team doesn’t. Direct sales exists because margin is higher and control over the customer relationship is tighter.

    Both motions have legitimate claims on certain deals. A mid-market opportunity that walked in through a partner’s existing relationship — whose deal is it? Does the partner get full margin? Does direct take over? Does the partner get a finder’s fee while direct runs the cycle?

    Without clear rules, both motions assume the deal is theirs. The partner assumes they own the relationship. Direct sales sees the account and assumes they’ll run it. The customer gets caught in the middle, with two people at your company competing for their attention and providing subtly different answers.

    How the Pattern Shows Up

    I’ve watched this pattern in telecom most vividly. A telecom vendor sells through systems integrators. An SI brings a deal to the direct team for joint pursuit. The direct team takes the meeting, closes the deal, and the SI gets a referral fee instead of the margin they expected. The SI learns not to bring deals to that vendor. The channel motion dies.

    In medtech, the conflict shows up between direct reps and distributors. The distributor brings the relationship. The direct rep shows up for the clinical conversation. The account compensation splits get negotiated deal by deal, which means every deal has internal friction. The friction compounds. The top distributors eventually move their business to competitors with clearer rules.

    In consulting, channel conflict shows up between owned delivery and partner-delivered engagements. A customer wants to use a partner’s team for an engagement the firm would have delivered directly. The economics of partner-delivery are different — lower margin, less control. The firm discourages it without saying so. The partner figures it out and stops bringing deals.

    The specifics differ. The failure mode is identical: ambiguous rules, inconsistent enforcement, channel partners learning through experience that the relationship is one-sided.

    The Three Structural Choices

    Companies that run channel well make one of three structural choices:

    1. Segmentation by account.
    Certain accounts are channel-only, certain are direct-only. No overlap. The rules are written down, shared with both motions, and enforced. This is the cleanest structure and the least flexible.

    2. Segmentation by deal size.
    Below X revenue, channel gets full ownership. Above X, direct takes the lead with channel in a supporting role at defined comp. This works when the threshold is well-chosen and respected.

    3. Deal registration.
    Whoever brings the deal first owns it, with defined rules for overlap and handoff. Requires a functioning deal registration system and discipline from both motions to respect it.

    Whichever you choose, the rule has to be written down, widely communicated, and enforced. The worst structure is “we’ll decide deal by deal” — that structure is how channel partners learn your company isn’t serious about channel.

    Compensation Is the Real Rule

    The written policy is only as strong as the compensation model behind it.

    If direct reps are comped on full deal value regardless of whether a partner sourced it, direct reps will try to take the deal. If channel account managers are comped only on channel-sourced deals, they’ll fight direct for attribution. If nobody is comped on joint-sourced deals, nobody works them.

    The compensation structure has to reward the desired behavior at both motions. Channel partners watch compensation design closely — they can tell whether your company is serious about channel by how your reps are paid, not by what your press releases say.

    The Diagnostic

    For your top three channel partners, ask: in the last four quarters, how many deals did they bring to you, how many did they refer elsewhere, and how did each of their sourced deals get compensated?

    If any of those numbers look worse than they did two years ago, the conflict has already been resolved — against the channel. You just haven’t told yourself yet.

    Channel motions die from compensation misalignment, not from strategic intent. Every executive I’ve watched try to fix a failing channel program by launching a new partner tier, a new marketing push, or a new certification program missed the actual problem.

    The fix is almost always in comp plan design. It’s the least glamorous fix and the one that actually works.

  • Narrative Architecture: Why Positioning Has to Live Everywhere

    Most founders and CROs think positioning is a deck. It’s not. It’s the narrative architecture that shows up in every touchpoint — and the organizations that get this right have a coherence that compounds. The ones that don’t have a thousand touchpoints saying slightly different things, all of which have to be re-explained every time a new buyer enters the funnel.

    Positioning isn’t the pitch. Positioning is what makes every pitch easier.

    What Narrative Architecture Actually Means

    Narrative architecture is the set of beliefs, language, and framing that runs consistently across:

    • Your website homepage
    • Your sales deck
    • Your cold outbound sequences
    • Your customer case studies
    • Your pricing page
    • Your demo script
    • Your press releases
    • Your executives’ LinkedIn posts
    • Your earnings calls (if public)
    • Your support documentation

    When the architecture is coherent, each touchpoint reinforces the others. A prospect who reads your homepage, gets a cold email, takes a meeting, and sees a demo hears the same story four times. By the time they’re making a buying decision, the positioning feels inevitable.

    When the architecture is incoherent, each touchpoint re-introduces the company. Sales is saying one thing. Marketing is saying another. The website is three versions behind both. Every conversation starts from zero, and the sales cycle elongates because the seller has to re-position the company in every meeting.

    The Four Layers

    The organizations I’ve watched build strong narrative architecture treated it as a layered system:

    Layer 1: Core claim.
    The single sentence that captures what you do and why it matters. Not a tagline — the foundational assertion. If you can’t fit it in one sentence, the architecture is already in trouble.

    Layer 2: Supporting beliefs.
    Three to five sub-claims that back up the core. These become the spine of your content, your deck, and your enablement. They’re the “because” statements that make the core claim defensible.

    Layer 3: Enemy definition.
    Every strong narrative has an enemy. Not a competitor — a problem in the world that your customers recognize and want to solve. The enemy is the status quo, the broken pattern, the cost of doing nothing. Without an enemy, you’re just another vendor. With one, you’re the solution to something the customer already believes is wrong.

    Layer 4: Proof.
    The evidence that makes the narrative credible. Customer stories, data points, case studies. The proof has to match the claim — if your core claim is about speed, your proof can’t all be about cost savings.

    Where Organizations Break This

    The failure mode is almost always the same: sales and marketing build the narrative separately.

    Marketing writes the website and the decks. Sales writes their own version in their outbound. Customer success builds their own messaging for upsell. Product writes a roadmap narrative that doesn’t map to any of the above. Each function is internally consistent; the organization is incoherent.

    The fix is structural: the narrative architecture has to be a jointly owned artifact, updated on a regular cadence, with all customer-facing functions represented in the review.

    I’ve watched companies cut their sales cycle materially — I’ve seen 20 to 30% reductions — just by aligning the narrative across touchpoints. The product didn’t change. The features didn’t change. The team didn’t change. The story changed, and the buyer no longer had to do the integration work themselves.

    The Diagnostic

    Take your three most recent customer-facing artifacts: your homepage, your latest sales deck, and your last cold outbound sequence. Read them in order.

    Ask: would a prospect encountering these in any order come away with the same understanding of what you do and why it matters?

    If the answer is no, you don’t have positioning. You have three different positions, and your buyers are assembling one of them from fragments every time they talk to you.

    The fix isn’t a branding exercise. Branding exercises produce logos and color palettes. What you need is a narrative architecture document, owned jointly by marketing and sales leadership, reviewed quarterly, and enforced in every customer-facing asset.

    Coherence compounds. Incoherence taxes every conversation.

    And the tax gets collected on every seller’s time, every marketing dollar, every customer meeting — in the form of buyers having to re-orient themselves to who you are every time they encounter your company.

    The companies that pay the tax usually don’t know they’re paying it. That’s the most expensive part.

  • The Pilot That Never Closes

    The pilot sounds like progress. You’ve got signed paper. Users are in the system. The customer is engaged. Then the pilot ends, and the expansion to full deployment just… doesn’t happen.

    If you’ve sold enterprise anything, you’ve lived this. It’s not failure — it’s a specific, recognizable failure mode, and the reasons are almost always predictable in advance.

    Here’s the pattern I’ve watched across medtech, telecom, and consulting: the pilot that looked like a win was actually a slow-motion loss, because the conditions for conversion were never built into the pilot design.

    Why Pilots Don’t Convert

    1. The success criteria were never agreed.
    The pilot started with everyone excited. Nobody wrote down what “successful” meant in specific, measurable terms. At the end of the pilot, the champion says “it went well.” The economic buyer says “I’m not seeing the ROI.” Both are right, because “success” was never defined.

    2. The pilot was run with different people than the full deployment would be.
    In medtech, the pilot runs in a single department with clinical early adopters. The full rollout would hit the whole hospital, including physicians who didn’t volunteer. The pilot users love it. The broader population was never consulted. Conversion requires convincing a new group from scratch.

    3. The economic model wasn’t agreed up front.
    “Let’s pilot it and see” usually means “let’s defer the hard budget conversation.” The hard conversation now has to happen after the pilot, at a time when organizational energy has already shifted to whatever’s next.

    4. The pilot outlasted the champion’s attention.
    You started with executive sponsorship. The pilot ran 90 days. Somewhere in week six, your sponsor got pulled into a reorg, a new initiative, or a different priority. By end of pilot, nobody on the customer side is actively driving conversion.

    5. The pilot became the solution.
    The customer got enough value from the limited scope that they didn’t feel urgency to expand. This is the most insidious one — the pilot was useful, just not useful enough to fund expansion. You accidentally built a free version that the customer never pays to upgrade.

    How to Design a Pilot That Actually Converts

    1. Write the conversion terms into the pilot agreement.
    Before the pilot starts, write down: if X outcomes are achieved, the customer agrees to expand to Y scope at Z price within W timeframe. This is not pushy — it’s just explicit. Customers who refuse to write this down are customers who are not actually planning to convert.

    2. Define success with the economic buyer, not just the champion.
    The clinical champion’s definition of success is different from the CFO’s definition of success. Get both in the room. Get both agreements in writing. In medtech, the clinical “does this work” answer has to match the financial “is this worth the cost” answer — and those are rarely the same conversation.

    3. Design the pilot to test the full deployment, not just the happy path.
    If the full deployment would involve users who aren’t clinical early adopters, the pilot should include some of them. If the full deployment would cross two departments, the pilot should cross at least two. A pilot that only validates the easy part tells you nothing about the hard part.

    4. Name the conversion owner on the customer side.
    At pilot start, the customer identifies the person responsible for driving conversion if the pilot succeeds. Not the champion — the conversion owner. Often this is the procurement or operations lead. Naming them forces the buying committee conversation earlier.

    5. Define the decision date.
    The pilot ends on a specific date. By that date, a specific decision must be made: expand, extend, or end. “Let’s keep going and see” is the failure state. Kill criteria or conversion — no middle path.

    The pilots that convert at the highest rates are the ones that look least like “try it and see” at the start. They look like clearly scoped experiments with written conversion terms, dual sign-off on success criteria, and a named date for the decision.

    A pilot without those elements isn’t a pilot. It’s a paid demo that lets the customer feel productive while not actually committing.

    If you’re running pilots that don’t convert, the problem is almost never the product. It’s the structure.

    Design the structure for conversion before the pilot starts, or accept that you’re designing for learning — and price the learning accordingly.

  • The Mutual Close Plan

    Most deals that slip in the final stages don’t slip because of product or price. They slip because the seller and the customer never aligned on what “closing” actually requires.

    The fix is a mutual close plan — a shared document, written between you and your primary buyer, that sequences every step required from both sides to get the deal signed, installed, and adopted.

    Done well, it’s the single highest-leverage artifact in enterprise sales.

    Done poorly (or skipped), it’s the reason your forecast looks clean at week six and then slides through the final three weeks.

    What a Mutual Close Plan Actually Contains

    1. The end-state definition.
    Not “signed contract.” A specific outcome: “Solution deployed to X users by Y date, integrated with Z system, with defined success metrics agreed by Q stakeholder.” If you don’t know what the customer is actually trying to accomplish, the close plan is premature.

    2. The decision path.
    Who specifically needs to sign off, in what order, and with what approval authority. Not titles — names. If your champion can’t give you names, that’s a diagnostic result: the deal is less advanced than the pipeline stage implies.

    3. The gating artifacts.
    What documents, meetings, approvals, or reviews are required at each step. Security review. Architecture review. Procurement review. Legal redlines. Pricing approval. Each of these has its own timeline, and they are almost never sequential — many can run in parallel if surfaced early.

    4. The dates.
    Specific, with joint accountability. “Security review by March 15, owned by customer-side CIO.” If the customer won’t commit to dates, the deal isn’t closing on your forecast timeline. The close plan forces this conversation while you still have time to react.

    5. The risks and mitigations.
    What could delay each step. What the contingency is. In construction, I saw close plans that specifically named bonding review as a risk with a mitigation plan. In telecom, security approvals were always the named risk. Naming the risk up front is how you prevent being surprised by it at week ten.

    The Structural Move: Make It Mutual

    The unlock is that this document is not your document. It’s theirs too.

    You draft it. You send it. You ask your primary buyer to review and amend. They own half the rows. The act of reviewing and owning commitments is itself a qualifying step — a customer who will not engage with a close plan is a customer who is not going to close. A customer who engages, amends, and adds rows is a customer whose deal is real.

    I’ve watched sellers resist this because it felt too formal or too aggressive. The customers I’ve watched respond to well-built close plans don’t find them aggressive — they find them useful. Enterprise buyers have their own internal processes they’re trying to navigate. A seller who helps them organize the process is a partner, not a pusher.

    The Diagnostic Value

    Here’s what a mutual close plan reveals that nothing else does:

    • Whether your champion actually has authority (if they can’t commit dates on behalf of their org, they don’t)
    • Whether the buying committee actually knows about your deal (if dates slip because named stakeholders weren’t aware, you’re single-threaded)
    • Whether the timeline your champion gave you matches reality (it rarely does, in the first draft)
    • Whether the deal is real (real deals absorb the close plan; unreal deals reject the close plan)

    Every one of those signals is worth more than the close plan itself. The plan’s real value is as a diagnostic instrument, not as a project management tool.

    When to Introduce It

    Mid-funnel, usually — after the solution is validated but before legal redlines start. Too early and it feels premature; too late and you’ve lost the opportunity to shape the process.

    For most enterprise cycles, that’s around the 40 to 60% complete mark in your pipeline stages.

    Write one this week for your highest-priority open deal. Send it to your primary buyer with a note: “I drafted this to keep us aligned on what’s needed from both sides — take a look and mark anything you’d change or add.”

    Their response — the speed, the thoroughness, the willingness to engage — will tell you more about the deal than any other single signal available to you.

    Most deals that slip in the last month did not look like they were going to slip until the last week. The close plan is how you see the slip coming at week three instead of week eleven.

    That’s the game.

  • Qualifying Out Is a Feature

    The mark of a mature BD operator is not how many deals they pursue. It’s how many they correctly walk away from.

    Most sellers are trained to qualify in — find reasons to keep a deal alive, extend pipeline, defer the hard conversation. Top sellers qualify out — they identify bad-fit deals early, end the cycle gracefully, and reclaim the time for deals that can actually close.

    This is counterintuitive in organizations that measure pipeline coverage ratios. If your quota coverage target is 3x, and you’re sitting at 2.5x, qualifying out feels like throwing away pipeline you need.

    That’s the wrong math.

    The Right Math

    A bad-fit deal has a low probability of closing, a long cycle, high support costs during the cycle, and — if it does close — high churn risk because the product wasn’t actually a fit. The fully loaded cost of pursuing it (seller time, SE time, deal desk time, legal time, executive time) often exceeds the contribution margin even if it closes.

    The seller who runs 3x coverage with 40% bad-fit deals is less productive than the seller who runs 1.8x coverage with 15% bad-fit deals.

    Quota coverage is a metric. Quota achievement is the point.

    Three Signals to Qualify Out

    1. The champion can’t articulate the consequence of not changing.
    If the customer can’t tell you, specifically, what breaks if they don’t buy — either the problem isn’t urgent or your champion isn’t the right person. In consulting, this was the reliable tell. Prospects who could not articulate what happened if they didn’t engage were prospects who would spend six months “evaluating” and never sign.

    2. The timeline doesn’t match the process.
    If the customer says they want to sign in 30 days but their org requires 90 days of legal review and procurement, the timeline is fiction. You have two options: reset the timeline to reality (which some customers will do, and that’s a good sign) or accept that the cycle will run longer than forecast (and price your forecasting accordingly).

    3. The deal is being shopped.
    Sometimes the customer has already decided — but needs a second quote to satisfy procurement. You’re the stalking horse. The tell: they move fast, they’re only asking pricing questions, they aren’t asking about implementation, and your champion isn’t really your champion. If the customer can’t introduce you to at least one other stakeholder, you’re a reference quote.

    How to Qualify Out Without Burning the Relationship

    Qualifying out doesn’t mean disappearing. The best sellers I’ve watched qualify out with precision:

    • They name the mismatch specifically: “I don’t think this is the right fit right now because X.”
    • They offer an alternative: “Here’s who I’d actually recommend you look at.”
    • They leave the door open: “If X changes in the next 6 to 12 months, call me.”

    This is the move that builds durable reputation. Customers remember the rep who walked away from their deal honestly more than the one who pushed through and then didn’t deliver. Six months later, the customer whose circumstances changed will call you first.

    In medtech, I watched a senior rep turn down a hospital deal because the procurement calendar didn’t align with the clinical urgency. The hospital’s own clinician thanked her for the honesty. Eighteen months later, when the procurement cycle reset, they closed a larger deal because the trust had been deposited.

    The Diagnostic

    Pull your pipeline. For each deal above your minimum threshold, ask three questions:

    1. Can the champion articulate the cost of not changing?
    2. Does the customer’s stated timeline match their actual process?
    3. Am I the second quote?

    If you get “no” on any two of those for a given deal, that deal should come out of your forecast. You don’t have to kill it — but you shouldn’t be committing it to your board.

    Qualifying out isn’t weakness. It’s the discipline that makes the in-deals close.

    The sellers who hit their number consistently are not the ones with the most pipeline. They’re the ones with the cleanest pipeline. That cleanliness comes from the willingness to say, early and honestly, “this one isn’t real.”

  • The Pre-Discovery Call: What to Do Before Your First Meeting

    By the time you’re on a discovery call, a significant portion of the outcome has already been decided. Not by you. By how much you know walking in.

    The pre-discovery call is the work you do before the customer ever sees you. Most reps skip it, run a generic discovery motion, and wonder why their win rates look nothing like their top performers’.

    Here’s what actually goes into a proper pre-discovery routine:

    Read Three of Their Recent Public Signals

    If they’re public, their earnings calls are a gold mine. If they’re private, their website press section tells you what they want the world to know. What do they say is their priority? What language do they use? What numbers do they cite?

    Walking into discovery able to say “I noticed on your last earnings call the COO emphasized X — is that informing what we’re talking about today?” changes the tenor of the meeting immediately. You’ve moved from vendor-asking-questions to peer-who-did-the-work.

    Know Their Competitors Better Than They Do

    In medtech, this meant knowing which clinical study was published about the competitor’s device in the last six months. In telecom, which regulatory filing their competitor just made. In construction, which project their competitor just won.

    Competitive awareness is not trying to sell against competitors in the first meeting — it’s showing the customer that you understand their market as well as they do. That’s a trust signal.

    Know the Person

    LinkedIn, a 5-minute Google, any podcast or interview they’ve done. You’re not trying to become their biographer. You’re looking for three things: what they’re known for, what they’ve said publicly about their current priorities, and who in your network might know them.

    The last one is the most valuable. A pre-discovery call where you realize you share a past colleague with the prospect changes the first meeting’s entire register. Reach out to that colleague before the meeting — not during — to confirm what you think you know.

    Map Their Org

    Before the call, sketch what you think the buying committee looks like. You’ll be wrong — that’s fine. Being wrong with a specific hypothesis is infinitely better than being blank. The hypothesis lets you ask sharper questions: “I’d guess procurement gets involved at some threshold — is that right?”

    Identify the Likely Silent Stakeholder

    From industry pattern alone, you can usually guess who’s going to kill the deal late if you don’t manage them early. In medtech, probably IT or supply chain. In telecom, probably facilities or the network ops lead. In construction, probably the bonding company. In consulting, procurement.

    Walking into discovery already hypothesizing who the silent stakeholder is lets you surface them in the first call instead of month three.

    Pre-Write Your Hypotheses

    The best discovery calls I’ve run — and the best I’ve watched others run — started with the seller walking in with three hypotheses: “Here’s what I think is happening. Here’s what I think is broken. Here’s what I think you’ve tried.”

    Then the call becomes the customer correcting or confirming each one. That’s a consultation. It’s also wildly more efficient than asking open questions and taking notes.

    The work takes 30 to 60 minutes per call. Most reps won’t do it because it’s unstructured and can’t be tracked in the CRM. Top reps will do it because the conversion delta is massive.

    Three quality checks for your pre-discovery:

    1. Can you tell the prospect something about their business they don’t expect you to know? If yes, you’ve done enough research. If no, keep going.

    2. Do you have a specific hypothesis about why the meeting is happening now? Not the BANT version — the real version. Something changed, or they wouldn’t be talking to you. What was it?

    3. Do you know one question you’re going to ask that they won’t have heard from another vendor? This is the question that makes you memorable.

    The discovery call that starts with “So, tell me about your business” is almost always run by someone who didn’t do their pre-discovery. It’s a signal to the customer that the seller didn’t do the work.

    Do the work before the meeting. Walk in already 40% of the way through discovery. The rest of the meeting becomes useful for both of you.

  • Deposits Before Withdrawals: The Sequencing of Trust

    Trust is an account. Most sellers overdraw it on the first touch and spend the rest of the relationship in repayment.

    The rule is simple and almost universally violated: deposits before withdrawals.

    Most sales training gets this wrong by teaching sequence-agnostic rapport. Be friendly. Find common ground. Take interest in the prospect. That’s not wrong — it’s insufficient. Rapport is not the same as deposit.

    What Counts as a Deposit

    A deposit is a specific, useful thing you give the other person that they did not pay for and cannot easily get elsewhere. It is not a “how are you” email. It is not a LinkedIn like. It is:

    • An introduction to someone they should know
    • A piece of information that changes a decision they’re making
    • A perspective on their problem that reframes it usefully
    • Free help on something adjacent to what you sell
    • A referral to a service provider (not you) that solves their problem better than you would

    A withdrawal, by contrast, is when you ask them for something:

    • A meeting
    • An introduction
    • A reference
    • A deal
    • A testimonial

    The mistake I see constantly — in every industry, at every seniority level — is reps making their first withdrawal before they’ve made any deposit. Cold email, cold LinkedIn, “quick question,” “15 minutes of your time.” First touch is a withdrawal. Every subsequent touch has to overcome the initial deficit.

    The Economics

    The operators who build durable pipeline invert this. First touch is a deposit. Second touch is a deposit. Third touch might be a deposit. By the fourth or fifth touch — which is often weeks or months later — the relationship has enough accumulated value that a modest withdrawal feels reciprocal, not extractive.

    In medtech, the reps who dominated their territory were the ones who sent their prospects clinical research papers relevant to the prospect’s specialty — unrelated to their own product — before they ever asked for a meeting. By the time the rep asked for 20 minutes, the prospect had already received two or three useful things from them.

    In consulting, the BD people who built the longest-tenure books did a version of this: they opened relationships with introductions, research briefs, or invitations to small events. By the time they pitched a scope of work, the prospect had already been in their orbit for six to nine months.

    This is slow. That’s the point.

    The economic logic: the value of a relationship built on deposits compounds. The value of a relationship built on withdrawal-first approach is capped at the individual transaction. First-touch-withdrawal gets you one deal, maybe. First-touch-deposit gets you a multi-decade professional relationship that throws off deals, introductions, and opportunities for both parties.

    Three Practical Moves

    1. Audit your first touch template.
    If your opening move is a pitch, a request, or a calendar link — you’re withdrawing first. Change it. The cost of the change is nothing. The return on it is enormous. Rewrite the first email to deliver something useful. Remove the CTA. Let the first touch stand on its own as a gift.

    2. Make your second touch more useful than the first.
    Most sales cadences degrade over follow-ups — the first email is thoughtful, the second is shorter, the third is a “just bumping this up.” Invert it. Make the follow-ups more valuable than the opening, not less. The prospect who didn’t respond to the first touch might respond to the third when the third is better than the first.

    3. Keep a deposits ledger.
    For the 20 relationships on your Relationship P&L, track what you’ve sent, introduced, or helped with. The ledger makes it visible when you’ve under-deposited. It also makes it visible when you’ve over-deposited without receiving anything — which is its own signal, usually that the other party isn’t reciprocating because the relationship isn’t real.

    The people who made their first withdrawal before a deposit are the ones who say “networking doesn’t work.” They’re correct about their experience. They’re wrong about networking. The mechanism was never going to work the way they ran it.

    Deposit first. Deposit again. Deposit until it feels slightly uncomfortable to not ask for something. Then ask — and watch the yes rate compared to everyone who asked in the first email.

    The math of the sequence is the whole game.

  • The Relationship P&L

    If relationships are a balance sheet asset — and they are, for anyone who sells — they deserve the same quarterly rigor as any other P&L line.

    Most operators don’t give them that rigor. Relationships get managed in a CRM if they’re lucky, in someone’s head if they’re not, and in neither if the relationship hasn’t been recently useful. Then a quarter turns soft, pipeline gets thin, and everyone is surprised.

    The fix is the Relationship P&L — a quarterly scorecard for the 20 relationships that actually drive your revenue, or will.

    How to Build It

    Step 1: Pick the 20

    Not 50. Not 100. Twenty.

    The constraint forces prioritization. These are the relationships that, if you lost them, would meaningfully change your next 12-24 months. Current customers, past customers, referrers, executive peers, advisors, and strategically important contacts you’ve been developing.

    If you can’t cut your list to 20, your list is wishful thinking. Most senior operators have three or four relationships that drive disproportionate revenue; another eight or ten that meaningfully influence it; and another six to eight that are strategic bets on the next two to three years. That’s the list.

    Step 2: Score Each on Five Dimensions

    1. Depth. How many substantive conversations this quarter? Quality, not count. A thirty-minute call where you actually learned something beats a quick email exchange, always. If your only contact this quarter was a happy-birthday LinkedIn comment, that’s a zero on depth.

    2. Direction. Is the relationship warming, cooling, or flat? Warming relationships are compounding. Cooling relationships are leaking value. Flat relationships are probably cooling — you just haven’t noticed yet. Direction is the most important dimension and the one people most often get wrong because they don’t want to see it.

    3. Debit/Credit. Do you owe them something? Do they owe you? A healthy relationship sits near zero — occasionally you do something for them, occasionally they do something for you. A relationship where you’re always in debit is extractive. One where you’re always in credit means you’re not receiving value — or you’re not asking.

    4. Decision capacity. What can they authorize, influence, or introduce? Not a judgment of their importance as a person — a specific answer to: in the current moment, what commercial capacity do they hold? People’s decision capacity changes when they change roles, companies, or scope. Re-score this every quarter.

    5. Time-to-ask. If you needed something, how long until you could reasonably ask? For some relationships, the answer is “today.” For others, “not for six months — we’re under-deposited.” That’s your signal about where to invest.

    Step 3: Review Quarterly

    Not annually. Quarterly. Relationships decay fast enough that annual review is lagging indicator.

    Set a recurring 60-minute block on the last Friday of each quarter. Walk the list. Note the direction, note what you need to do, schedule the touches.

    Step 4: Act on the Review

    The point of the scorecard isn’t the scorecard. It’s the actions that come out of it. Every review should produce:

    • A short list of relationships that need a deposit (coffee, intro, note, useful share)
    • A shorter list of relationships where the time-to-ask is now zero and you should ask
    • An even shorter list of relationships to retire from the top 20 — because they’ve become transactional, the other party has moved on, or the relevance has faded

    The hardest part of the scorecard is the retirement column. Most operators never remove anyone from their top 20, which means the top 20 just accretes over time and becomes meaningless. Pruning is maintenance.

    What the Best Operators Do

    Every senior BD operator I respect has some version of this list. Some keep it in a spreadsheet. Some in their CRM with custom fields. One kept it on an index card in his wallet that he rewrote every quarter. What matters is that it exists, gets reviewed, and gets acted on.

    Most relationships don’t die from conflict. They die from neglect. The Relationship P&L is the forcing function that makes neglect visible while it’s still reversible.

    Build the list this weekend. Twenty names. Score each on the five dimensions. You’ll find out something uncomfortable — usually that your single most valuable relationship hasn’t been touched in four months.

    That’s the discovery. That’s the value of the exercise.

    Act on it Monday.