By the time you’re six months into implementation, you’re underwater and the customer is disappointed in a product that was never designed to do what you promised. The relationship is worse than if you’d said no in the first place.

The counterintuitive truth is that customers don’t remember that you said no. They only remember that you didn’t deliver. Here’s how to avoid it.

This post covers:

• How to reframe a feature request before you react to it

• How to use your existing customer base as a reality check

• How to pressure-test requests with data before they make it onto a roadmap

• How to build a backlog that makes customers feel heard

• How to phase solutions so deals close, without commitments you can’t keep

Most custom requests aren’t actually custom

Whenever a customer asks you for something that sounds custom, your first question should always be, “What problem are you trying to solve?”, not “What do you want?”, or “How do you want that to work?”

Most custom feature requests are solutions your buyer has half-designed in their head and gotten overly-excited about. Your job is to put on your PM hat and walk them back from the edge by clarifying the problem rather than engaging in the solution.

Many requests are workarounds for something your product already handles differently. In that case the gap isn’t in your product, it’s in how they understand it. A good discovery conversation followed by a tailored demo or training session closes that gap without a single line of custom code.

Use your customer base as a reality check

Turn the feature request into a benchmarking moment by saying something like: “Most of our customers solve that problem like this _________ . How does that compare to how your team operates?”

Doing this accomplishes two things. First it grounds their request as an outlier in a broader reality, which signals that this may not be as universal a need as they think. Second, you show that you see patterns across accounts, which demonstrates the depth of your understanding and builds credibility.

If their answer is “actually that’s the same for us,” you may have just diffused the whole request. If their answer is “we actually do it differently,” you’ve just learned something useful and can move onto the next test.

Pressure test with their own data

Customers tend to overweight the importance of edge cases because they consume disproportionate mindshare — the unusual is more exciting than the mundane. Your job is to re-balance this against the 90% of their business that already runs smoothly but never comes up in conversation.

3 questions to ask to do this are:

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Traditional SEO is a ranking game, where you’re competing for position on a results page that a human then chooses to click. By contrast, GEO is a citation game, where you’re competing to be the source an AI model references when it generates an answer. No click required, no position one to aim for. It simply comes down to, does the model trust your content enough to quote it.

That shift sounds subtle but it isn’t. A 2025 analysis of 300,000 keywords found that AI Overviews correlate with a 34.5% drop in average CTR for the #1 organic result compared to similar queries without them. The traffic model is breaking. If you’re still measuring success purely through rankings and click-through rates, you’re optimizing for a game that’s getting smaller.

This post covers:

• What actually changes between SEO and GEO; ranking vs referencing

• The 9 tactical shifts that matter, with examples of how to implement them

• Where GEO and SEO genuinely overlap

• An honest state of where GEO is right now

The shift from being ranked to being referenced

In traditional search, your own well-optimized pages could rank on their own merit. Write good content, build some links, structure it properly, Google notices, users click.

GEO doesn’t work that way. AI search shows a systematic bias toward earned media over brand-owned content. Much stronger than traditional search algorithms ever did. What you publish on your own domain matters less, whereas what gets written about you, by sources the model already trusts, matters enormously.

That’s the biggest strategic reorientation. Not a tactical tweak.

9 tactics that move the needle

1. Earned media is your highest-leverage investment

Getting placement in authoritative industry lists, round-ups, and third-party reviews isn’t a PR nice-to-have anymore. It’s a primary acquisition channel. When AI engines are asked to recommend tools in your category, they pull from sources they trust. If you’re not in those sources, you’re invisible.

This is the sharpest break from traditional SEO. Own-site authority still matters, but it no longer carries the conversation.

2. Write for machine scannability, not for human delight

AI search engines don’t surface the most insightful content. They surface the easiest-to-parse content. Practically, that means:

• Short paragraphs of two to three lines max.

• Bullet points and numbered lists wherever a sequence exists.

• Lead each section with one or two sentences that directly answer the heading.

• Use a consistent answer pattern: definition → detail → example.

Semrush’s research confirms this. Structure beats prose when machines are the primary consumer.

3. Target conversational queries, not typed keywords

The way someone prompts ChatGPT is different from how they’d type a Google query. Traditional keyword tools miss this entirely. “Best CRM for SMB” becomes “what CRM should a 20-person B2B company use if they’re moving off spreadsheets.”

You need to research how your audience actually phrases questions to AI assistants and then write content that answers those specific phrasings directly.

An easy way to do this research is to ask each LLM, "What questions do people ask about [your topic/product category]?" or "How would someone ask an AI assistant to help them find [your type of product/service]?" The models will surface natural language patterns they've been trained on.

Another way is to filter your Google Search Console queries for long-tail, question-based queries (anything starting with "how," "what," "why," "best way to," etc.). These are the closest proxy for AI-style queries, and they'll show you what's already driving impressions even at low volume.

4. Make your content quotable

AI-generated answers are essentially assemblies of citations. The content that gets cited is content that can be dropped in without editing; concise definitions, clean numbered steps, specific observations that stand alone.

For example, imagine you are trying to show up in AI results for the question, “what is project management software and why do teams use it?”:

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The mistake most founders make is treating this as a pricing negotiation. It isn’t. It’s a risk psychology problem dressed up as a procurement conversation. The buyer isn’t trying to get a discount—they’re trying to protect themselves from looking stupid in front of their CFO six months from now. Caving on price doesn’t solve that. It just makes you cheaper and still loses the deal.

Here’s how to actually handle it.

This post covers:

• How to diagnose what the buyer is actually afraid of

• A two-tier license structure that resolves the commitment standoff

• How to build a rollout plan that sells itself internally

• A template you can steal

Diagnose the real objection

Before you restructure anything, figure out what you’re actually dealing with. There are two types of hesitation, and they require completely different responses.

The first is procurement theater. “The space moves quickly” and “we don’t want to be locked in” are negotiating lines—not real blockers. If you hear these from a VP of Finance you’ve never met who just joined the call, that’s theater. Push back: “If the space didn’t move at all, would you commit to annual?” Watch what happens.

The second is genuine internal risk. The champion likes your product but is worried about sponsoring a tool that gets replaced in 90 days. They’re not scared of overpaying—they’re scared of looking bad. That’s a political problem, and no discount fixes it.

Once you know which one you’re dealing with, you can respond to the actual objection instead of the stated one.

Build a two-tier license structure

Stop trying to force every buyer into a single contract type. The structure that works is simple:

• Annual committed licenses — lower per-seat price, unlimited usage, full production access. For teams that have already validated value and are ready to commit.

• Evaluation licenses — monthly, usage-capped, priced 20% higher than the annualized equivalent. For teams that haven’t piloted yet and need a structured on-ramp.

The pricing differential matters. If evaluation licenses are cheaper or equivalent to annual, you’ve just given buyers a permanent workaround to avoid committing. Price them higher—not punitively, but enough that committing is the obvious rational choice once a team has validated the product.

Cap the usage on evaluation licenses aggressively enough that buyers can assess value but can’t run production workflows on them. If someone can do their full job on an evaluation license, they will—and you’ll never convert them.

Write the rollout plan before you send the proposal

This is the part most founders skip, and it’s the most valuable thing you can do in a complex enterprise deal.

A rollout plan is a one-page document that shows by team, by quarter which groups start on annual committed licenses, which groups start on evaluation licenses, and when each evaluation group converts to annual. It answers the question every internal champion eventually has to answer upward: “What does full deployment actually look like?”

Build it before the proposal goes out. Use what you know from deal conversations to date i.e. which team piloted, which teams are next and what their rough timelines look like. Make it concrete with real team names and real dates.

The rollout plan does three things at once:

1. It gives your champion something to present. Internal approvals require internal selling. A concrete deployment plan is a better artifact than a quote.

2. It de-risks the purchase for finance. The CFO isn’t worried about this quarter’s spend, they’re worried about runaway expansion with no governance. The rollout plan shows there’s a process.

3. It locks in the expansion conversation before the deal closes. You’re not just selling the pilot team. You’re selling the whole org on a timeline.

You’re not solving a pricing problem with this document. You’re solving a political one.

Set a quarterly true-up cadence

Monthly billing reconciliation on flexible licenses creates admin overhead that kills relationships fast. Move everything to a quarterly true-up cadence. Every 90 days, you reconcile usage, convert any evaluation licenses that hit the conversion criteria, and adjust seat counts.

This gives buyers the flexibility they think they need while giving you the predictability you actually need. It also creates a natural checkpoint to revisit expansion without making it feel like a sales call every month.

Cap monthly active users

One guardrail that doesn’t get talked about enough: cap the monthly active users (MAU) on evaluation licenses, as well as the usage itself. Without a cap, buyers will quietly use evaluation licenses for real production work across their entire org and never convert.

An MAU cap keeps evaluation licenses working as intended i.e. a structured assessment window, not a permanent workaround. Set the cap at a number that’s enough for a real pilot but not enough to scale across a department.

The rollout plan template

Most enterprise deals that stall on the buyer saying, “we’re not ready to commit” aren’t really about commitment. They’re about a champion who doesn’t have enough cover to go to bat for you internally. The two-tier license structure buys them time but a rollout plan buys them credibility to get the deal done.

Here’s a template for the rollout plan and instructions for how to adapt it and how to use it in your deal conversations:

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The conversion problem isn’t awareness. It’s signal. You have no idea who’s behind those downloads, and GitHub isn’t going to tell you. It could be a mid-market product team that’s been hacking together deployment scripts for six months and is one production incident away from buying a real solution. Or it could be a grad student who downloaded your framework for a class project. Treating those two the same is how you waste six months of sales motion on the wrong people.

Here’s what actually works.

This post covers:

• Why most open-source users will never buy and how to stop chasing them

• How to build visibility into an anonymous user base

• How to qualify for commercial potential, not just enthusiasm

• How to use community channels to surface real pain

• How to structure a concrete upsell path that closes

Most of your open-source users are not your customers

Open source functions as a freemium front door. It’s excellent for research adoption, benchmarking, and getting your framework embedded in early-stage technical decisions. It’s terrible for direct conversion if you don’t do the work to figure out who’s actually behind the usage.

Two groups will never buy from you but they’re often the loudest in your community:

• University researchers. No budget, no infrastructure headache at scale, and often a cultural disposition toward building over buying. They’ll contribute PRs and open issues and love your product. They will not send you a PO.

• Not-invented-here engineering teams. These are deep-technical, engineering-led orgs that genuinely enjoy building infra. They treat your open-source framework the same way they treat everything else: a starting point for their own custom system. You’re not losing them to a competitor. They just aren’t buyers.

Stop optimizing for these groups. They inflate your community metrics and dilute your pipeline signal.

Build visibility into your anonymous user base

Accept the constraint upfront: GitHub downloads give you a number, not a customer list. You cannot build a sales motion on a download count.

The fix is straightforward, but most teams skip it because it feels like friction—and they’re worried about slowing adoption. Don’t be. The teams with real deployment problems will still show up. You’re not filtering out buyers; you’re filtering out noise.

Here’s how to surface real identities:

• Waitlists for early access features. Gate your most useful production-grade features behind a lightweight signup. You get an email, a company, and a reason they’re interested.

• Community onboarding in Discord or Slack. When someone joins, ask them one question: “Are you using this for research, a side project, or something in production?” You’ll be surprised how directly people answer.

• Early access programs tied to specific use cases. “Apply for early access to our monitoring module” tells you exactly who’s trying to solve a real operational problem.

None of this is complicated. The good news is the bar is still low as most open-source companies aren’t doing any of it.

Qualify for commercial potential, not just interest

Not all users with real jobs at real companies are buyers. You need to segment, and you need to do it early.

The segments that matter:

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And yet founders keep defaulting to it. The logic goes: build a big list, drop in a template offering some asset, turn the sequence on, and watch the replies roll in. Spoiler alert, they don’t.

The good news is you almost certainly have data sitting in your CRM and analytics tools right now that can get you 5–10x better reply rates than basic cold email. You don’t need to hand-research every prospect to craft the perfect message. You just need to segment prospects by psychological state and write copy that meets them where they actually are.

This post covers:

• Why psychological state is the only segmentation variable that matters

• 7 psychological segments you can build from your own first-party data

• Email messaging templates for each segment

• Sequences and subject line tests

Relevance beats volume every time

The reason most outreach underperforms has nothing to do with deliverability or send time or whether you used their first name in the subject line. It’s that the message doesn’t match where the person is in their head.

Someone who ghosted you after a demo is in a completely different mental state than someone who filled out a form but never booked. Treating them the same way with the same template, the same offer, the same tone is leaving money on the table.

Each of the 7 segments below has a distinct emotional context. Match the copy to that context, and your reply rate will stop being embarrassing.

7 segments

1. Closed lost - timing not right

These are your warmest leads. They didn’t reject you, they rejected the timing. That’s a fundamentally different no, and it deserves a different response.

A low-pressure, short “checking in” message is all you need here. The goal isn’t to re-pitch. It’s to reopen the door and see if the conditions have changed. Don’t recap your entire value prop. Don’t attach a case study. Just acknowledge where things were, note that circumstances change, and make it easy for them to raise their hand.

Overselling here actively hurts you because it signals you don’t remember the conversation, which destroys the rapport you built during the original deal.

2. Closed lost - price too high

Never lead with a discount. It tells the prospect you were overcharging them, which either confirms their suspicion or creates a new one.

What works instead is reframing the ROI or introducing a lower-commitment entry point e.g. a pilot, a stripped-down tier or a bundle that changes the maths. The goal is to make the economics feel different without signaling desperation. If you’ve genuinely improved your pricing model since the deal closed, by all means lead with that but if you haven’t, lead with the outcome they’d be buying, not the number.

3. Closed lost - feature gap

These contacts need to see proof, not promises. A message that says “we’ve improved a lot since we last spoke” lands with exactly zero credibility. Specifics do.

If you’ve shipped the feature that killed the deal, lead with that concretely. Name the feature, explain what it does, link to documentation or a short demo. If the feature still isn’t there, don’t waste time reaching out.

4. Closed lost - ghosted

Keep it short. A three-sentence email with a dead-simple yes/no CTA outperforms anything polished and long. Long emails go unread, especially from someone who’s already tuned you out.

The frame that works: pattern interrupt. Something that acknowledges the situation without assigning blame, creates a low-friction path to re-engagement, and respects their time. “Still worth a conversation?” is more effective than three paragraphs explaining why you’re still a great fit.

5. Booked demo - no show

Don’t ask why they didn’t show. You’ll come across as passive-aggressive, even if that’s not the intent.

Just make it easy to rebook. Acknowledge upfront that schedules get chaotic. It gives them permission to re-engage without embarrassment. Offer a specific slot rather than “let me know when works” so it removes one more decision from their plate. A time-bound nudge (”I have Tuesday at 2pm or Thursday morning”) performs better than an open-ended invite.

6. Filled the lead form - didn’t book a meeting

They raised their hand but something stopped them from taking the next step and it’s almost never the product.

The friction is usually informational: they don’t know how long the demo is, what they’ll actually see, or whether they’re about to get a 45-minute sales pitch dressed up as a product tour. Address those objections directly in the email. Add one line of social proof (a recognizable customer name, a specific outcome) to tip the confidence needle. You’re not re-selling, you’re removing the last obstacle between them and the calendar.

7. Site visitor - de-anonymized

This one requires the most care because these people have not opted in to anything. All they did was look at a page on your site. If you lead with “I saw you visited our pricing page,” you’ll come across as creepy/desperate.

The only play that works here is leading with value e.g. a relevant insight, a resource, or a point of view tied to what they were looking at. Build credibility before you ask for anything. If they were on your integration page, send something useful about the category they’re likely evaluating. Earn the right to the next conversation rather than demanding it.

Email templates

To get you started, I’ve put together templates for each of the 7 segments that meet the prospect where they are in their head. The templates are available to paid subscribers at the link below:

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Everyone assumes joining a successful startup is easier than a zero-to-one build. It’s not. The pressure is higher, the appetite for failure is lower, and the company keeps growing whether you’re adding value or not. Nobody’s waiting on you to save the business, which means nobody notices if you’re quietly spinning your wheels.

The biggest mistake first marketing hires make is going top-of-funnel too fast. They launch brand campaigns, redesign the website, build out a content calendar, all before understanding what’s already closing deals at the bottom. Months pass, budgets burn, and the sales team is no better fed than the day you walked in.

The fix is to do the opposite. Start at the bottom of the funnel and work your way up.

This post covers:

• How to define the one metric that actually matters

• What to do in week one before you open a single Google Doc

• How to map the inbound engine before you touch it

• Why your first campaign should amplify, not invent

• How to put a real number in front of the team within 30 days

Define your north star metric before you do anything else

Your first conversation with sales leadership should produce one thing: a single shared KPI that everything you do gets measured against.

At an inbound-led B2B company, that number is almost always demos booked — not leads generated, not MQLs, not traffic. Leads are a vanity metric until someone picks up the phone. Every campaign you run, every channel you test, every piece of content you publish gets judged against demos booked. If it doesn’t move that number, it doesn’t matter.

Get this aligned in week one. If sales and marketing are optimizing for different things, you’ll spend six months producing work that impresses no one.

Spend week one in listening mode, not planning mode

Get into the Slack channels where deals are actually won and lost.

Find the deal negotiation threads, the closed won alerts, the closed lost alerts and the demo booked alerts. Read them obsessively for a week. It’s market research better than any win/loss survey or customer interview program and you don’t have to build anything to do it.

What you’re listening for:

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The real moat against a cheap incumbent copycat isn’t just price and feature parity; it’s a combination of usage habits, proven value, additional hooks into painful adjacent workflows and flipping the loss-leader logic.

Here’s how:

• Segment your customers to identify your risk

• Polish your ROI story

• Flip the loss-leader logic with an 80% copycat of your competitor

• Run a targeted customer success motion

Segment your customers to identify your risk

Use a simple 2x2 where each quadrant represents a distinct customer type based on how much they use your product and how sensitive they are to price:

Choose the most applicable of the following options to define your high/low break points for usage:

• 70%+ of licensed seats provisioned and used

• Consuming 60%+ of plan tier usage limit

• Adopted 60%+ of key features

Choose one or more of the following to define high/low break points for price sensitivity:

• Has (or has requested) a discount

• Is on a month-to-month contract if your standard is annual

• Bottom quartile of ACV

Polish your ROI story

Document the core value drivers of your product and the ROI you’ve driven to date. Common examples are:

• Incremental revenue generated (jobs done x revenue generated per job)

• Total time saved (jobs done x time saved per job)

• Qualitative feedback from your most active users. Set up 1:1s with them and ask, “How has your day-to-day changed since you started using [product]?”

More on this topic here:

Design an “80% copycat” of your competitor’s product and flip the loss-leader logic

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While this can seem like an immediate deal-killer the reality is you can still close the deal while your SOC 2 is still in progress. What actually wins enterprise deals is confidence, documentation, transparency, a predictable roadmap and no surprises. Basically make it boring and procedural.

Here’s how:

• Control the narrative early

• Build a SOC 2-in-progress security packet

• Anchor on risk, not on checking the box

• Offer compensating controls

• Use social proof and exec pressure strategically

• Separate security review from legal review

Control the narrative early (pre-questionnaire)

Don’t wait for procurement to escalate your lack of SOC 2 Type II. As soon as the deal starts moving, bring it up proactively:

“We’re currently in the final stages of SOC 2 Type I, with Type II following. I’m happy to share our control matrix, policies, and timeline.”

This signals maturity, prevents surprise objections and keeps you in control.

Build a SOC 2-in-progress security packet

Buyers mainly want proof you know your risk surface. Create a reusable folder that includes your:

• SOC 2 timeline: date the auditor was engaged, audit period dates, expected issuance date and Type I vs Type II clarity

• Control matrix: covering security, availability, processing integrity, confidentiality and privacy.

• Core policies: for access control, incident response, data retention, secure SDLC and vendor management.

• Subprocessor list: include vendors like AWS, Stripe, Open AI

• Pen test executive summary

Anchor on risk, not on checking the box

Security teams ultimately care about risk transfer. Your controls matter more than the Type II certificate itself.

Frame your response as:

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They’re so full of jargon, hyperbole and recently-invented categories-of-one that the visitor is left asking themselves, “WTF does this company actually do?"

I give you Exhibit A:

…and Exhibit B:

…and Exhibit C:

Don’t leave your visitors scratching their heads. Instead do the following:

• Get your headline right

• Explain how it works (in plain language)

• Drive to a single call to action

Get your headline right

Your headline (and sub headline) is the first thing your visitors see, so it needs to instantly communicate what you do. Start with a customer-centric, literal headline that communicates either the job you do or the specific outcome you deliver in one, short sentence. Then use a sub headline to clarify either how it works or whom it is for in one, longer sentence.

Here are some great examples of headlines and sub headlines (all at seed-stage companies):

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In my experience, a lot of startups have poorly structured agreements because a lot of startup founders’ lawyers reuse old contracts to save time on drafting without adequately reflecting on how realistic the contract is for their client’s size and stage.

This post lays out eleven best practices for structuring your agreements as an early-stage startup to ensure a speedy legal review. Note that this post is not legal advice. I am not a lawyer. Think of it more as a checklist to evaluate your current paperwork and discuss it with your own lawyer.

1. Use a separate Master Services Agreement (MSA)+ Order Form to speed up review.

Doing this separates your legal terms (in the MSA) from your commercial terms (in the order form), allowing for each document to be reviewed and negotiated by the relevant expert (the MSA by a commercial affairs lawyer, the order form by finance/procurement) and reduces the likelihood of lawyers trying to become procurement heroes and vice-versa.

2. Write in plain language to reduce misinterpretation

Lawyers distrust unclear drafting and will respond with heavy edits. To avoid this happening write in short sentences, make minimal use of defined terms, avoid triggering terms like “including without limitation” and “sole discretion” and avoid confusing double negatives such as “fail not to”, “not uncommon”, “cannot not” and so on.

3. Start from market-standard positions to avoid redlining battles.

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There are two ways to measure the ROI of a product. Either you show how much it increases revenue or you show much it reduces expenses. However, many sellers make the mistake of thinking there’s also third way — showing how much time it saves — only to get shot down when their deal hits the CFO’s desk for approval.

In this issue:

• How to show the ROI based on increasing revenue

• How to show the ROI based on reducing expenses

• How to show the ROI based on saving time

How to show the ROI based on increasing revenue

If your ROI story is based on increasing revenue, you need to be able to prove it directly and quickly in a time-limited trial in order to have a predictable motion for customer acquisition.

For example, my client Ajax is an AI timekeeping solution for mid-size law firms which finds billable hours that were missed and attributes them to the relevant matter. To show the ROI, the Ajax sales team runs a pilot with new customers to track how many incremental hours the software finds, divides the value of the additional billable hours by the cost of the software and shows a healthy return on investment (typically 10x or more), making it an easy decision for the buyer to approve. After all, who doesn’t love found money.

How to show the ROI based on reducing expenses

If your AI product replaces an existing legacy tool at a lower cost the ROI story is fairly straightforward. The customer buys your product, rips out the old product and as long as the new and existing contract terms don’t overlap too much, they are guaranteed to reduce their overall expenses.

For example, my client Surface Labs has an AI solution for marketers that combines multi-step forms, lead nurturing, lead scoring, qualification and routing in a single product that replaces tools like Zapier, Chili Piper and parts of a CRM at a lower cost. This makes it an easy decision for marketers looking to consolidate vendors, reduce tool spend and increase website conversion.

How to show ROI based on saving time

If your AI product saves time, simply showing the amount of time saved is not enough.

Nor is simply asking your buyer, “What would you do with those time savings?” and using their answer, “We’ll be able to spend it on more important things” as your ROI justification. As a former COO, I lost count of the number of times people on my teams pitched me to buy salestech that would enable them to “spend more time selling” only to fold when I asked them if they’d be ok with a higher quota.

Nor is translating time savings into a dollar amount e.g. if each person on the team saves 10% of their time and makes $100k/year salary then the time savings are somehow magically worth $10k/year. This is meaningless unless the buyer is planning to reduce headcount.

The only way to predictably show the ROI from time savings is how it increases the capacity of an existing team without having to add more people to the team:

For example, several of my clients sell AI products that reduce the time taken to perform repetitive tasks; Scope reduces the time to produce industrial inspection reports, Fleetcraft reduces the time to complete aircraft maintenance paperwork, Henry reduces the time to produce commercial real estate pitch decks, Tracelight reduces the time to produce financial models in Excel.

For all of these companies the ROI story has a similar structure:

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While your champion buys software maybe once every couple of years and needs your help to guide them through the process, your procurement contact does it for a living and has their own playbook of psychological tricks negotiation tactics designed to pressure you into submission.

Common procurement tactics include:

• “Your competitors are cheaper”

• “Our budget is fixed”

• “These are our standard terms”

• “The CFO won’t approve this”

• “This may slip into next month / year”

• “You need to run everything through me”

• Giving you the silent treatment

This issue covers how to specifically deal with each of these tactics plus some background on how Procurement fits into the overall company structure.

Contents

• How procurement teams are measured

• Why Procurement is not as powerful as you think

• How (not) to negotiate with Procurement

• How to counter common procurement tactics

How procurement teams are measured

In most companies the Procurement function sits within the Finance department and is measured primarily on maximizing commercial terms in favor of the company. e.g.

• Maximizing discounts

• Putting in caps on annual price increases

• Eliminating auto-renewal provisions

• Lengthening payment terms

In some companies Procurement is also measured on minimizing risk (e.g. liability, compliance, security), however the negotiation of those pieces is typically farmed out to other teams (e.g. Legal, Compliance, InfoSec, IT) with Procurement just coordinating the results and summarizing them for final review.

Why Procurement is not as powerful as you think

If you take Procurement’s words at face value it’s easy to fall into the trap of believing that they have the power to kill your deal. That’s just not how it works.

The reality is that budgets are owned by department execs (e.g. CMO, CRO, CTO, CISO, CHRO, CLO, GC etc, sometimes VPs), not by Procurement.

If an exec wants to buy software or services and has room for it in their budget, Procurement can’t block it. You’re more likely to get blocked by InfoSec or Legal for security or compliance reasons than you are by Procurement for commercial reasons.

All that Procurement can do is try to negotiate the best commercial terms they can tell their boss (the CFO) how much they saved and justify their existence.

How (not) to negotiate with Procurement

The two basic rules for negotiating with Procurement are

1. Never negotiate over email. Instead get on a call with them. Procurement usually gets introduced to you via email, so check their email signature for a phone number and give them a call. They’ll probably answer and will be taken off guard.

2. Never negotiate until you have a verbal commit from your champion. Knowing the willingness of your champion (and exec sponsor) to move forward with you is essential for navigating Procurement.

Here’s what to say when they answer:

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Knowing that closing a deal almost always requires getting multiple stakeholders engaged, this puts you in a tricky position. Do you run everything through the gatekeeper and pray they perform for you or do you go around them and risk pissing them off?

This issue breaks down the problem, covering the following topics:

• The two types of gatekeeper

• The one simple rule for dealing with gatekeepers

• How to get what you need out of a gatekeeper

• How to go around a gatekeeper

The two types of gatekeeper

• Wants to look good to their colleagues. This is the type of person who wants to be up to date on the latest tech trends so that they can say something smart when they come up in a discussion. You know you are dealing with this type if they ask you for a lot of information but don’t provide much in return e.g. they want your deck and POV on strategy and competitors rather than digging into their problem and your solution.

• Wants to avoid looking bad to their colleagues. This is the type of person who either thinks salespeople are idiots who don’t understand the unique culture at their company, or is exploring vendors without approval from their boss, or is just a control freak. Bottom line; they don’t want you interacting with their colleagues in case you make them look bad. You know you are dealing with this type when they tell you that everything needs to run through them and won’t bring other stakeholders into calls.

The one simple rule for dealing with gatekeepers

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When sellers aren’t prepared to handle bake-offs they typically make one or more of the following mistakes and botch the sale:

1. Knocking the competition — “Oh, we win against them all the time”, “I’ve heard some horror stories about them” etc. While sellers think this persuades buyers to favor them, the reality is it just makes them trust them less.

2. Excessively talking up your product — “We have everything they have, and more! Let me tell you about it…..”. As with sales in general, the more you dominate the conversation talking about your product, the less you learn about what your buyer actually cares about.

3. Unnecessary discounting — “We’ll beat anyone on price”. Unless you are selling a pure commodity, price is seldom the top criterion for buyers. You’re just negotiating against yourself.

Instead, use the following steps to stack the odds in your favor:

• Use a rubric to determine the evaluation criteria

• Use the evaluation criteria to position against the competition

• Optimize the evaluation process

• Focus the evaluators on the evaluation criteria

Use a rubric to determine the evaluation criteria

When your buyer mentions they are looking at multiple options, resist the urge to start knocking the competition, talking up your product or talking down your price. Instead switch into a consultative mode by helping set the rubric:

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The common misconception is that an ask for the business is some grand moment of truth in a sales process when your pitch reaches the peak of it’s crescendo and your buyer can’t help but succumb to your sales charms. The reality couldn’t be more different.

Deals are not won and lost in one magical moment. They’re won in a series of smaller, almost innocuous commitments made by the buyer to the seller during the sales process; sharing information, providing feedback, attending meetings and bringing in stakeholders. The more of these smaller commitments a buyer makes, the more likely they are to also make the commitment to spend money.

However, you can’t rely on your buyers to volunteer these commitments. You need to be explicit about asking for them, starting in your first meeting and continuing throughout your sales process. This issue covers what those key moments and commitments are and how to ask for them, including:

• How to ask for information during discovery

• How to ask for feedback in a demo

• How to ask for the next meeting

• How to ask for more stakeholders to be involved

• How to ask for a signed contract

How to ask for information

These are generally easy asks to make but are key because they get your buyer warmed up to sharing information. A buyer who is cagey about sharing information at this stage is unlikely to become a customer.

• During intros: “How about we kick off with some intros. I’m _______, co-founder of _________. We help {customer type} do {job/use case}. Would love to hear more about your role at {company} and what you’re hoping to get out of today’s call.”

• Probe for problems: “Most of our customers have one of the following problems [list problems]…Curious, which of these resonates most with you?”….”How often do you run into that?”

How to ask for feedback in a demo

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The key to running a successful group demo is to get most of the members of the group talking, so that they come off mute, turn on their cameras, air their questions and concerns live and start to have their internal discussion with you in the room — giving you a chance to shape the outcome in your favor.

This post covers everything you need to plan and execute a group demo, including:

• How to prepare for a group demo

• How to open the call and get people talking

• How to run the demo and drive a discussion

• How to wrap up the call and maintain momentum

How to prepare for a group demo

If you’ve had a positive intro call with a potential champion, ask to meet with them ahead of the group demo to prepare. Ideally ask this at the end of your intro call, otherwise ask once the group demo has been scheduled:

• “Can we chat briefly before next week’s group demo? I’d like to make sure I understand who will be there and what they’ll want to see so that the meeting goes smoothly. How does [date/time] work?”

Once on your prep call, start to ask questions about the stakeholders:

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While it is relatively easy to book an intro meeting with an innovation manager, it is also incredibly common for nothing tangible to come from it as innovation managers have neither the operating responsibility to champion a purchase nor the executive authority to sign off on it.

It’s easy to get lulled into a false sense of security during an intro call as your innovation manager will appear super interested (after all their job is about talking to interesting startups) and ask you to send a copy of your slides to circulate internally but if you leave your first meeting with that as the only next step you won’t turn the conversation into a concrete sales opportunity.

The key to successfully selling to an innovation manager is to treat them more like a conduit than a champion — focus more on understanding the organization, stakeholders and process and less on mining for pain points and pitching your product. Doing this well requires you to modify how you run your sales calls. This post gives you a guide on how to do that and covers:

• How to run an intro call with an innovation manager

• How to follow up after an intro call

• How to prepare for a group call

• How to run a group call

• How to leverage an innovation manager during a POC and procurement

How to run an intro call with an innovation manager

The primary goal of your intro call is to identify the group of stakeholders who are likely to be interested in your solution and the process for getting in front of them.

This means that you don’t want to spend time trying to mine for the innovation manager’s pain points, as they aren’t the champion.

Instead, modify your discovery to quickly start talking about the group that the innovation manager works with and what their problems are. Use the following questions as your guide:

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