The one thing the best companies do is remain flexible at all times. The MOST irritating thing for your buyers, advocates, and users is to come off as the “my hands are tied” rep/sales leader/founder/exec. You have to get creative. This does not mean caving and bending at the will of your customers, but you shouldn’t make it about you. The customer is buying, not you.

I’m sorry to say, but regardless of your current ARR and success as a company, there are far too many options and replacements of your solution. There are many skilled and hungrier GTM teams ready to rip you out of your most exciting deals.

Remain flexible, be thoughtful, earn trust, win on value.

Best of luck to EOY to those who celebrate. Go kick some ass.

Most will say, “this keynote (or feature) validates what we’re building,” but I think that's the obvious takeaway. If you reflect on how a competitor or Bigco with a competitive feature are presenting at the keynote, are you using the same exact language, or are you positioning how and why you are different both technically and value-wise? The worst thing you can do is sound the same, even if your product is superior. What you want to take away from the keynote is the language they’re using and see how you can outmaneuver on the ground game. Are they making bold claims on performance? Go beat them on POCs. Are they making bold claims on features and capabilities that you’ve had for years but your product has far more depth? Prove it. This is not a perspective on over-rotating product announcements from other companies as an existential threat but an opportunity to start the upcoming year strong as users and buyers start drawing down from their massive commitments on cloud and infrastructure spend in 2025/26.

So, as you work on positioning or competing with deals going into end of year and early next year some questions to consider: how is your product truly differentiated (you don’t need to do “first principles” things, just be honest about your capabilities)? Do prospects see the value on the first call or are they getting peppered with discovery questions? Why would someone choose you as a long-term partner? What are you building that shows depth (ie your roadmap) that makes you stand out as the visionary in your category that shows you will outpace the keynote promises?

Leverage the legwork massive teams put together to build their messaging strategy via keynotes and use it to your advantage to win more deals than ever.

For early-stage companies with stellar sales skills or advisors who can help generate revenue, it’s very common to see sales acumen propel a company to its first $1M+ in ARR. While this is an important milestone, it’s just a starting point. Early revenue should confirm that what you’ve built is not only sellable but also repeatable and essential for your market.

In these stages, revenue is only one of several critical signals of success. The use cases you solve along with how “repeatable” and “pain-relieving” your solution is needed to serve as proof points for future growth. Testimonials from customers and buyers should clearly validate that your solution delivers definitive value, solves a real need, and positions your company as a long-term partner. This is what separates market disruptors from those that simply meet a revenue milestone (remember, you’re trying to build a company that hits $100M+ in ARR…!).

Using the lens of a Founder, Investor, or Customer: which type of company would you rather run, invest in, or buy from?

Company 1

• 9 paying customers, all using the product differently

• Broad use cases but no deep expertise or focus in any single one

• Operates in a crowded market where competitors look relatively similar

• They win because they’re the easiest to buy from

Company 2

• 10 paying customers with two very concrete, well-defined use cases

• Still a new entrant in the market but moving quickly, shipping key features that set them apart

• Buyers are aligned with the company’s vision; most buy for what the product offers today, and roadmap items are natural extensions of proven strengths

• They, too, are easy to buy from but they stand out by solving specific, repeatable needs

Deciphering (and more importantly differentiating) between key milestones like hitting $1M in ARR or achieving PMF is what separates the good fundraises and scale from the greatest fundraises and fastest growing companies. The best founders we know are able to celebrate each as "wins" without conflating the two and will be the ones everyone wants to emulate.

Where teams go wrong is trying to rely on benefits-driven or performative language without clearly explaining what the product actually does. Saying something like “making engineers more efficient” isn’t a real value proposition — every tool a developer buys is expected to improve efficiency in some way.

One thing we often remind technical Founders of when pursuing sales or GTM for the first time is that their entire jobs prior to starting a company was about excruciating attention to detail, systems thinking, and getting into each tactical step to ship something great. The first sales and GTM process should actually feel similar. Performative language and rushing to ROI discussions misses the point of what you need to do first: get people to easily understand the value it provides and for users to love your product. Until then, it will be very hard to tell the story or articulate the ROI and value of your product. It first starts with tactical workflow diagrams, step-by-step walkthroughs of how users should use your product, then simplifying for people to deeply understand so you can identify if your product is resonating with the right audience(s). 

If you don’t have a clear hypothesis on how people use your product and the problem you are aiming to solve for them on a daily basis, you should take a step back and define this first. This is important it will be very hard to get meetings (either through referrals or cold outbound) if people don’t know why they are being asked to take a call. This does not mean you will have the right product at the beginning but people must understand what they are looking at to give feedback or feel compelled to test-drive your product. Better upfront clarity and expectation setting allows for better feedback.

To better develop and refine a clear value proposition to show the problem you solve, first have a clear understanding of the below, then work on defining a 1-2 sentence explanation of what you do: 

• Who benefits most from your product? The safe answer everyone often starts with is “VP of X,” but often, they are the beneficiary of their teams getting value. The VP is rarely the person who will use or benefit from the daily use of the product itself

• What does your product actually do that is unique and different from your competitors? Everyone loves to start with a 2x2 diagram putting their logo in the top right corner, but what about your product actually makes it earn that spot in the top right corner? Can you prove it? 

  • Explain how the product works not “it will make you more efficient” 

  • Don’t use fluffy language like “single pane of glass,” or “turnkey” explain what the end user should experience

• If you showed your mockup or v1 of the product can people follow the claims? What specifically do people say, ask, and positively reinforce that you can use in your problem statement

• Pivoting and iteration often come from: learning your product isn’t adoption or purchase-worthy, or that what you aim to build is far too great of a promise to start, so you need to refine how you get someone to get to value faster. Remember, niches are okay (to start)

A few resources we recommend as well:  

• Positioning Guide - MKT1

  • Positioning Teardown - MKT1

• On Developer Marketing - Lee Robinson

If you feel your hypothesis is strong to start, here’s what you can do to make sure you get the feedback you need to succeed: 

• Prepare for the call – use the research to validate or inform how you’ll drive the hypothesis on the first call

• Don’t ask for pain (yet), validate the problem you’re solving – there is nuance on how you ask discovery questions

• Be definitive – validate your hypothesis with clear direction

• Inspire the next step – be clear on how a prospect should engage with you

We’re always here to support!

• Start with an overview of the Business Case – How does this tool help us meet a company’s objectives for the year?

• What is the current problem you’re solving? – Problem and solution must be clear and understandable by the person presenting to Finance 

• Why now, why anything? 

• Defining the value driver you solve for – Increase revenue, reduce costs, reduce risk 

CFOs are incredibly busy and so are the other counterparts on Finance teams. This means you probably won’t get the meeting with an incredibly important person, so your business case must be well understood and agreed upon by your Champion in advance. We recommend you deeply understand the stakeholders involved: Budget Owner, Economic Buyer, Signer. 

To increase your chances of winning over Finance, whether you can meet with them directly or not, work on answering as many of the questions below as you can. It feels pedantic and yes, you may be able to close without this, but this will increase your likelihood of hitting your number this quarter. Avoid slipped deals at all costs! 

Qualification 

• How experienced of a buyer (or evaluator of software) is the person I’m working with? The more they can answer below themselves, the more experienced they likely are. This matters because you are trying to reduce the risk of Finance rejecting or scrutinizing what is put in front of them

• Why does the prospect need us now? What has changed for them (challenges, limitations, etc.)?

• Is there approved spend? If not, do we have access to someone who has the authority to find the funds? (More on this here) You want to make sure Finance isn’t concerned about overspending or misuse of funds 

• Is leadership comfortable buying from a startup? Have you confirmed this? 

Business Case

• Which of the three are you helping with?

  • Increasing revenue

  • Reducing costs (includes efficiency) Note: “making developers 2x more efficient” is not enough :) 

  • Reducing risk (often for security) Note: most companies need a specific solution in security, so you need to highlight the “cost of doing nothing” 

• What does this help the company achieve that is tied to a major initiative for the year?

• Are you replacing an existing solution? If so, how and why should they change now? Do you know when the renewal is? 

Instilling Confidence in the Approval Process

• Have you shown the prospect your roadmap? What are they most excited about? Any contingencies before purchase? 

• Have you shown them what an onboarding plan will look like? (More here)

  • This means, do they need to add more team members to your product? 

  • Are there any additional integrations or migration work post purchase? 

  • Are there timeline slides you’ve created to show this? 

  • Are there any additional costs they need to consider? 

• Is Pricing clear? 

  • Have you shared the details on your model? 

    • Regardless of usage vs. seats, this needs to be super clear – planned usage, what happens at scale, what happens in Year 2+ if successful.

      • Note: you probably don’t need multi-year and you don’t want to piss people off who are clear they don’t need it

      • Note 2: Most don’t need the highest pricing option – we strongly recommend a Partnership Onboarding Plan to avoid heavy discounts or a disappointing outcome on the size of the deal

By doing the above—plus the work to secure the Technical Win, build a compelling business case, and develop strong alignment with the Signer—you position yourself more strategically to close the deal. This will give you and your Champion the confidence to win over Finance regardless of the chance to meet with them. 

People want fast, ‘easy-to-use’ products that ‘improve our efficiency.’ The problem with software and buying software is that it’s rarely fast (even when people say they’ll buy quickly), tools are rarely easy to use (sorry), and ‘efficiency’ is a blanket statement that leads to ‘ROI’ metrics at which CFOs roll their eyes (and sometimes laugh).

Customers have far too many options to sit through a 30-minute discovery call without seeing your product. A highly contested and debated topic is whether you should demo on the first call. I’m here to say you’re doing your pipeline and top-of-funnel efforts a disservice by not doing this but how you demo and what you discuss are the main failure points companies encounter on the first call.

More questions and discovery aren’t necessarily a good thing; quality questions and quality discovery are what matter most. That’s what you must make as easy as possible for prospects.

Some thought starters for approaching quality questions & discovery heading into your first discovery call (reminder: all highly customizable based on your timing, product, use case, etc)

0 minutes – Do research or waste valuable time on the first call

You should prep—even if you’re a solo team and an expert Founder-led seller. You want to be able to teach your future team how to approach a call and, more importantly, why. I’m also sorry to say this, but this is far more important than creating an ICP document with blanket coverage on 'who we target,' because you’re demonstrating the creative thought process behind why this is a potentially valuable prospect and what a great call at your company looks like.

First 5 minutes – Stop asking for budget, authority, and need so quickly. If they can’t fit your technical profile, you can save yourself time since they can’t buy anyway. 

What are the three main criteria that, if unmet, would allow you to end the call early? For example, if a prospect needs to have a cloud environment and you don’t confirm what cloud they’re on in the first two minutes, you risk wasting 28 more minutes—only to find out at the end that they’re required to be on-premise. Some may argue, 'Well, it might be worth it,' but you could use those 28 minutes productively rather than spending a full hour across two calls trying to convince them you’re a fit when, in reality, they weren’t qualified from the start.

Example of three primary questions to ask: 

1. “Looking at your job posting, I saw you all use AWS, is that right? Are you using a solution to solve [the problem you solve], or exploring what’s out there?” 

• Note: With the above, we have identified: Do they fit our tech stack, are they using a competitor, or just kicking the tires. 

• Why this matters: If not a fit on tech stack, now you can qualify here. If they are using a competitor, figure out why they are seeking a new solution if they already have a tool in place. 

2. “Since this isn’t a new market, you are probably familiar with a lot of the general capabilities. On our first call, we typically show a high level demo of our product to explain where we can add value. Is it most helpful to walk through a general demo of the product, or highlight the main differentiators on why we stand out?” 

• Note: Rather than asking “what’s your success criteria,” or pitching against a competitive solution, you can now uncover what’s most important to the prospect today, giving you a nice segue into asking “why are these the most important capabilities to you?” 

• Why this matters: People want to see the product, but the failure mode of demoing on the first call is not understanding what the prospect is seeking and why. This gives you the permission to ask many relevant questions before the demo rather than confusing people why you are asking questions without context.

3. “Okay, this has been super helpful. Before I show you the product, can you walk me through how you typically evaluate solutions and if you’re planning to include others in the process?” 

• Note: Don’t ask for someone’s boss (yet). You’ll piss them off.

• Why this matters:  You need to earn the permission to make the ask for them to include relevant stakeholders (yes, this includes their boss and eventually the signer), but devaluing the person giving you the time on the first call is a great way to lose their trust and scratch your head asking yourself why they went dark on you after the first call. 

Next 15 minutes

Show the product based on what you’ve heard, focusing on high-level details. They don’t need something bespoke on the first call—save that for the 'next call.' Traditional guidance suggests doing deep discovery to create a personalized demo for the second call. The problem is, the prospect is likely talking to three or more other vendors that week and won’t remember filling out your verbal checklist. They’ll remember which solutions seemed most engaging and best aligned with the primary problems they need to solve. 

• Example: “Aanya, you mentioned at the beginning of the call that you built an agent to solve this, but the main challenge isn’t putting it in production. The challenge was that as it runs and customers interact with it, it’s hard to track the success, is that right? Awesome, so to start, let me show you how we solve for this and I’d love to ask you more about where things break down to make this capability more relevant to you.” 

Next 5 minutes 

Q&A. Instead of asking, “So, what do you think?” or “What do you think are the next steps?” try asking, “Based on what you shared with me at the beginning of the call and throughout the demo, we covered X, Y, and Z, which should help address Solution 1, Solution 2, and Solution 3. Assuming I’ve got that right, what questions do you have to better understand if we’re the right fit for your team?'”

Next 5 minutes 

Sell the next meeting. Rather than “okay, let’s book a time now,” for the sake of booking the next meeting, tell them what the next meeting will be based on what you discussed. For example, “so, I’m really glad you brought up these questions today. As I mentioned, the demo we went through is just a quick runthrough of the features based on what you shared with me, but as a next step, we’d love to do a more fully detailed demo based on your requirements. Assuming that works for you, when is the best time for you to meet next?” 

What sets this approach apart is the delivery and sequencing. Remember, it’s highly unlikely that you’re the only solution in the market for a prospect. This means you need to show, tell, ask, and sell more assertively. Take all the best practices from traditional selling and weave them into a modern, rapid-fire approach to win more deals—and win them faster.

The game ain’t the same

A few months ago, the Amplify team wrote a post on sales prospecting becoming an engineering problem. As we at Dynamic work with more modern technical teams, we continue to see amazing things built with modern GTM stacks that make the formerly tedious parts of outbound obsolete. This is not AI-SDR-agentic-workflows. What I really like about Tim’s POV in this post is that only one of the key components is AI focused, meaning you can do more with less through modern tooling (IP lookup/enrichment, Sales-focused email, text generation, glue tools) and that this trend will continue regardless of the “hype cycle” of AI. 

The failure mode we often see is that teams try to offload sales or automate pipeline building too quickly without a deep understanding of who they’re engaging with and why, what “qualified” looks like, and reviewing learnings, failures, successes each week allow you to instrument a process that people can follow as you build your organization. This must be figured out by the Founding team first. We feel strongly about this principle because Founders often forget “the eye” they start to build for what a strong fit customer and a poor fit customer is from a very nuanced POV. 

You cannot assume anyone you hire will ever have the same “eye” and therefore you must understand your prospecting “process” at which you can scale your team around – which happens to be so much more powerful than the traditional approach of list building with ZoomInfo and spamming through Outreach. 

The future is actually great for introverts (and extroverts who want to win)

The people best suited for the future of sales are: technical, process-oriented, and skilled writers. What this means is that technical Founders are well equipped for the future of where GTM is headed. It’s why this is such an exciting future for what’s ahead and why traditional approaches to sales feel increasingly distant as prospects prefer to buy and engage with companies in a very different way. Learn your process, use data, debate, iterate, find success, and teach more people on your team how to think critically and creatively about approaching your ideal customers. 

More from “sales prospecting is becoming an engineering problem”:

For founders today, the question becomes: Who do you hire to build and manage these pipelines? I’m starting to steer the companies I work with towards a combination of a few things:

Some technical skill: you don’t need someone who can code, but you do need someone who’s reasonably comfortable with Zapier and webhooks.

Process and product mindset: you need someone who takes joy in building new processes and fine-tuning them over time, plus is excited about finding and getting to the bottom of new products.

Copywriting: great writing is always a standout skill, and with all of this automation, the SDR of the future will be able to spend more time writing better, more compelling templates.

Essentially, you are building a cross functional team that would include both your first seller and an ops/systems generalist. As this matures as a discipline, founders should expect their first sellers and more specifically their sales leader to become an expert at managing and automating these kinds of prospecting pipelines. And like with other things related to AI and automation, reducing manual work in one area means more time and energy for the work that really does require a human touch. 

We totally agree with this and have continued to see sales and GTM turn into an even more meaningful “team sport” since a group of generalists who are excited to build something great are deeply invested in finding true advocates and adopters of the products they love to promote (the companies they work at). So, as you’re thinking about your hiring plans for next year and how to allocate time, dollars, and focus, consider how to build a process that leverages the pipelines and tools of the future, allowing you to do 100 times more than you thought possible with the small (but mighty) team you have.

Go make it happen.

The conventional approach is to answer the "what is your ICP" question but that frankly limits what many companies need to solve at the early stages in this new wave of models and AI-first companies. People genuinely don't understand how amazing and how easy it is to build certain features now. As exciting as that sounds, it can also make your life a lot harder.

Maybe you've started to do services-esque-work on a specific set of product requirements but your customers’ asks for product requirements continue to stretch your team too thin on an already compounding backlog... 

This is where you need to start defining what your product does based on what you’ve built for the initial cohort of companies using your Product. You must define what is table stakes, what is uniquely differentiated, and what is the specific workflow that will allow your Product to get Technical Wins. If you can't, keep digging and here’s an example below. 

Here’s what your v1 should start to look like to teach people how to evaluate and how to translate this to value of your “Product”

Start with a general overview for someone to ground themselves on what your product is supposed to do so they can better understand how to evaluate your solution and eventually (key word eventually) articulate the value of what your offering and how it’s better than their current approach today: 

Define 2-3 primary things your Product does today that get people to experience the value (even if they don’t know it yet)

1. AI-generated suggestions on your code

2. AI-generated code reviews on code selections or your entire codebase

What you will evaluate when using our Product for [X days] 

1. Accuracy of suggestions and the quality of what you ship. (Bonus points if its faster)

2. Accuracy of recommendations and the output of the quality of what you ship. (Bonus points if its faster) 

How using {{Product}} compares to your previous workflow 

(Simplified example – should be more specific and granular based on your solution)

If you’ve already mastered the above, now is the time to start building guardrails on feature requests. As a repeat set of problems to solve emerge from quality customers, now you’ve started to find fit. Repeatability isn’t just about consistently bringing in revenue, it’s solving a repeatable problem that brings in revenue and helps you get to your first $10M+. 

You may know how to drive an evaluation and people are open to purchasing your product, but the repeat challenge is prospects need that other feature you don’t quite have yet. This will be an ongoing challenge regardless of how successful you become, but it’s important to start being more definitive on what you can offer vs. constantly being an “everything for everyone” solution. 

What {{Product}} will help {{Prospect}} achieve

1. AI-generated suggestions on your code

2. AI-generated code reviews on code selections or your entire codebase

3. Future: Roadmap item being released next month. We’ll signal this is being built, but you’ll make the purchase on the above. We commit to this. Note: this should be something you were already planning to build, but were hoping for a customer like this to make the ask to pull it forward.

   1. You also don’t need to commit to #3 until you have alignment from someone who would sign off on the purchase. More on this here, and we’re always happy to share some tactics on softer approaches that are not “give me your boss or we’re parting ways.” 

What you will evaluate when using our Product for [X days] 

1. Accuracy of suggestions and the quality of what you ship. (Bonus points if its faster)

2. Accuracy of recommendations and the output of the quality of what you ship. (Bonus points if its faster) 

3. Future: Should have a material positive impact on the customer and why they’re asking for it. You want it to be the functionality that makes the Product experience better for other future customers. 

Where {{Product}} stands out in comparison to your previous workflow

(See above for reference) 

Best Products will allow you to make the best repeatable revenue business out there.

Great sellers want to come in, drive deals they know will close, based on product availability today, and sell vision for the product’s future with as few promises as possible. In the early days, especially in the world of AI Agents where “real” use cases are still being defined, you need to be product-minded.

What often happens is Founders find a few key customers (or maybe reach the first $1M+ in ARR) and then aim to hire an AE. I’ve even written quite a bit about when to hire an AE and how to interview for that role. Upon reflection, I believe that the first “sales” hire Founders should make is actually someone who can relieve you of technical constraints. Customers want to talk to Founders; they want to be sold by the person who created the company. If you can solve true product problems and make your product excellent, as the amazing engineer that you are, then you should find someone to complement you in scaling that process. You should continue to sell the product, learn how to sell the next large deals and test how much more Product work is required to go up-market.

As your technical GTM hire becomes successful and self-sufficient, you can then start hiring an Account Executive who is eager to deeply understand the product and serve as a strong counterpart to the technical hire. At this stage, you have built a great team—you’ve become a “front-line manager” of GTM and now you can focus on how to scale and execute effectively.

Early-stage companies need independent, creative thinkers who are obsessed with solving problems. The best hires want to solve problems and understand that they will be well compensated once they solve big problems, whether that’s now or in the future. The main issue I see with Account Executive hires is that most just want to make money and close deals (this is a great thing and you want salespeople to make a ton of money), but Founders are often caught by surprise when Account Executives aren’t proficient with the product and fall back into their traditional ways of “selling the way [I’ve] always sold.” It’s incredibly difficult to get this right, but what I recommend is finding ways to make your developer experience, customer experience, and product absolutely top-tier, so it becomes obvious for world-class Account Executives to want to join and collect paychecks by selling the value and true ROI of all the amazing things your product can do.

If the prospect doesn’t have a solution yet

• You should ask: “If you decide to do nothing, what would happen?”

• Why this matters: If the prospect can stick with what they have and your solution is only slightly better, it’s usually easier for the prospect to stick with what their doing. What you need to do next is  find out their workflow to uncover the potential root cause of their challenges today. 

If the prospect is already using a competitor

• You should ask: “It’s always going to be easier to stay with {{competitor}} since you already have an agreement. It sounds like we are uniquely different for X and Y reasons. If we can solve what we discussed, how likely are you to switch to us?”

• Follow up question: It’s best practice to ask, “when is the renewal for {{competitor}} and do you plan to replace them before or at the time of your renewal?” We see teams get burned all the time by not asking this question. They run an amazing evaluation only to find out they’ll need to wait 8 months to replace their competitor who now knows you are a threat and have 8 months to fix their product and keep you out of a deal.

• Why this matters: Although you may know exactly why a prospect should use you because your competitor has an inferior product, it’s always much easier to stick with whatever solution the prospect already has than to purchase something new. You must get the prospect to identify a set of criteria in which they will evaluate your solution that proves how and why it is better and different than the competition. You as the Founder and/or seller must prove it is better by helping define the success criteria that allows you to stand out in comparison to the previously chosen vendor. 

If the prospect is on open-source and wants to purchase your solution

• You should ask: “We make open-source easy for you to get value and unless you need {{differentiated Enterprise offering(s)}} why would you purchase from us?”

• Why this matters: Your open source offering is there for letting people build. If they haven’t built enough to know the value of your offerings, why would they then move to a commercial solution not having tried open source first? If they are already using open source, do they have any legitimate issues that would cause them to buy from you? 

If you have a self-service / free option and a hand raiser requests the Enterprise tier

• You should ask: “It sounds like you’re already getting plenty of value from our current tier, which we love to hear. Given this upgrade to Enterprise will require an evaluation and formal process, what prevents you from staying on the current plan?”

• Why this matters: You’d be surprised how often customers don’t realize how far they can get and how much they can pay your company without needing to run a formal sales evaluation. You will build immediate trust and eventually drive much larger deals if you get the prospect to value quickly, get a technical win with very few obstacles (ie your sales process), and then build a business case for $100k+.

There are a multitude of other steps required to execute a deal but to prevent expending too many calories and effort on a deal just to find out you lost it can be prevented by asking questions like the ones above.

There of course can be scenarios where it’s out of your control but teams should only make that excuse after they’ve pulled all of the stops on a deal. Here are some resources to dig into based on given scenarios to make sure you have done the things in your control first: 

1. Ensure you have the technical win (and confirmed it) 

2. Build a mutual action plan without being awkward to clearly define the key stakeholders and steps to reduce risk in your deals (it should never feel like homework for either side) 

3. Know the difference between the signer, budget owner, and buyer and that you have access to the right person (are you sure you know the difference?)

4. Align  with the end user and an executive sponsor

5. Devise a thorough internal security process to avoid failing security reviews (SOC 2 Type 2 is just a starting point)

6. Build a close plan (handling internal sales is as important as handling external sales)

7. Define a business case that will work when it lands on the CFOs desk (I also love this post on the topic and highly recommend) 

8. Accurately forecast based on the deal size and the stakeholders involved to ensure you know how long the deal will take to close

9. Build a Partnership Onboarding Plan to avoid presenting pricing only to learn the prospect needed to spend a lot less to get started

10. Sell a roadmap but do not underdeliver – the best teams know how to position “what can we sell now, what can we prove, and what about our vision can we get the customer excited about post-purchase?”

11. Align the pricing proposal with expectations vs. pushing for the big-ticket deal upfront

Founders with sales teams should do the following:

1. Make sure you hire(d) the right Account Executive

2. Created a safe space for the team to share learnings and blockers to avoid getting caught by surprise on issues you should have known about sooner

3. Make sales a team sport in your company

Questions? Feedback? Let us know.

What ended up happening? People would receive a handmade version of what they had envisioned for their homes, which delighted the customer but likely made the artisan cringe, knowing what could have been possible. This highlights a disconnect between the customer's vision and the true value of handmade goods.

What does this have to do with enterprise software? I see Founders and sellers asking customers to lead the discussion and it’s a backward way to run any customer engagement. If there’s only one takeaway from this post, let it be this: stop asking your customer, “So, what do you want to do with our product during this POC?” or “What do you think is a good next step?”

If you don’t inspire and guide your prospect in how they should engage with your business, expect scenarios and responses like but certainly not limited to:

• “Let me get back to you once I talk to my team. Can you send the recording?”
  (They didn’t talk to their team, and they probably forgot the recording existed.)

• “Hey, we really enjoyed the conversation, but we decided to evaluate [Competitor] because they have features X, Y, and Z.”
  (You’re frustrated because you have those features too, but the prospect didn’t get it. Now you’re spending time convincing them the competitor isn’t as good, and you never hear back.) You must demonstrate and inspire what’s possible at every step of the customer engagement process—from your documentation to your website to your sales approach.

  • Reminder: you must be objective. Do you have the features, and do you offer true differentiation compared to alternatives? If not, is this a “product issue” or a “sales issue”? It’s likely a combination of both, but good discovery will help you understand your true limitations in the deal.

So, where do you start? Begin by reviewing how you conduct discovery and pitch your product (avoid asking for pain, instead walk them into it). By the end of your first 1-2 calls, do you fully understand your customer’s workflow?

Start with the workflow

When it comes to workflow, the most successful teams present a diagram or workflow using tools like Excalidraw or FigJam to visually show the customer where their company fits into the value chain. This approach also helps uncover challenges in certain areas. For example:

Rather than relying on vague success criteria, guide your customers on how they should be using and testing the product. Encourage them to focus on your differentiators and unique features. Don’t assume they will immediately understand or appreciate these on their own.

For instance:

“We think your focus on ease of use is great, but let’s define this based on what you’ve shared with me so far. Specifically, what makes this easy?” “Great, so customers like ours use us because we automate that entire process end-to-end, whereas you're doing it manually. Let’s make sure you try that and compare it to how you’re doing it today.”

This approach helps you get more specific about their success criteria and highlights how your product stands out as a vendor.

Lastly, there are three key steps to earn a POC, win a POC, and ultimately secure a customer:

1. Deliver what people expect and want – This starts with strong positioning and a strong pitch. How often are people seeking clarification on what you do and why? 

2. Get the technical win – Prove the product’s value and demonstrate true differentiation (technical wins, win deals).

3. Sell roadmap – People aren’t just buying what you offer today; they need to be inspired by what’s possible and what they can expect from you as a long-term partner, so sell your roadmap.

Remember, people buy from people!

The most common person companies/sellers have access to is someone who can get internal approvals done to purchase your software. This is not the Buyer.

Let’s break down each key persona: 

The Economic Buyer

They have veto power to push the project forward or to stop it regardless of other stakeholders position such as your Champion/Counter Champion.

Their focus is in line with the strategic objectives of the organization. You are likely to be able to read about their role or initiatives in the annual report.

They have access to discretionary funds that aren’t budgeted.

They are likely to have profit and loss responsibility.

They will sign your contract, or be a part of the approval process leading to signature. - Source: meddicc.com

As a Founder/Executive, you should have access to the person who can push the project forward. You can leverage this alignment at strategic parts of the deal rather than trying to sell to them directly throughout the sales cycles. Remember, this person will still likely ask “What does my team think?” 

What I want to highlight here that’s incredibly important is “they have access to discretionary funds that aren’t budgeted.” You should never lose on budget if you have a compelling business case and alignment with a buyer. 

They “will sign your contract, or be part of the approval process leading to signature” for every deal, you should know who signs the contract. It is not always the Buyer. 

The Signer

To avoid confusion, when working with the primary decision maker — or even someone who says, 'The business is following my recommendation, it comes from my budget, and I want to move quickly' — ask a straightforward question: 'Okay, that’s great to hear. So, if we meet your requirements by X date, can you sign the agreement?' If the answer isn’t a direct 'yes' and they can’t walk you through the entire approval process leading to the signature, you need to identify the Signer. You can also leverage a Mutual Action Plan to make this line of questioning more specific and collaborative. 

Let’s say Finance is The Signer in this case. As the Signer, they are the final team/person to authorize a purchase by reviewing your budget, need, and other internal guardrails to avoid frivolous purchases. This means you need clear justification on why a purchase is being made so the signing process is a breeze. This does not mean that Finance is the Economic Buyer. This also means you still need to know who makes the final approval on the Buyer side to ensure your software “is in line with the strategic objectives of the organization” per the definition of the Economic Buyer above. 

I highly recommend this post (not mine) for all Founders and ellers. It’s a fantastic primer on how to approach and get signatures by Finance. 

The Budget Owner

Can a Budget Owner be the Signer? Maybe. Can a Budget Owner be the Economic Buyer? Perhaps. But it’s incredibly rare for a Budget Owner to be all three — let’s figure out how to discern. Often, there are a list of approval steps to complete before signing. Anyone who has sold software has gone through this frustrating experience: you work with someone who says, 'I’ve got this, and I promise to get it done before the end of your quarter,' but the deal doesn’t close until three weeks later.

The Budget Owner may only be able to purchase up to a certain dollar amount and may not even be able to make any purchases without approvals from: 

• Their Boss (may also not be a “Buyer.” Example: VP of Engineering may be able to sign up to $75k without any approval but anything above that must be approved by the CTO who also needs to get Signing authorization from Finance) 

• Finance (see above)

• A peer they actually share a budget with because it’s “a bit of a slush fund” and most teams are actually terrible at managing their P&Ls and budgets – they split this on a quarterly basis and no one really knows how much they have. (Ever been asked if you can “reduce it down by $2k?” Ever wonder why?) 

To identify the persona you are working with, use this walkthrough as a way to get comfortable asking while not putting the Budget Owner on defense but instead leverage them as a collaborative partner to help facilitate the transaction smoothly and turn them into your biggest Champion and Advocate in the process. 

The above may feel a bit obvious in hindsight but as you work with any prospects going forward, ask them to walk you through their entire signing process and you’ll learn a lot about who you’re actually working with and how you can get that deal you really need to celebrate at the end of the quarter. 

Good luck out there! 

If you’re a Founder learning sales (or have experience in sales), hold yourself accountable so you can learn this inside and out and enable your team with the same mindset when you’re ready to hire your first Account Executive (AE). While none of this is groundbreaking, it's a valuable reminder to always approach calls with a plan. No plan, no solution! If you already have AEs on your team, ensure they are properly preparing before entering any customer conversation. We recommend asking them the following questions about their upcoming calls to gauge their readiness. If they can answer these questions clearly, your team is well-prepared.

What does the company we’re talking to do? 

• It's one of my favorite questions to ask. Most people don't truly understand what their prospect does or how their solution could support the prospect's workflow. You'd be surprised how often teams fail to conduct a thorough review of their prospect's business. At a minimum, this should be your primary step before any discovery call.

  • As an example, if you're an ML infrastructure company, it's crucial to understand how machine learning integrates into your prospect's organization. You should know:

    • How does ML fit into their organization today? Is it a primary or secondary focus? 

    • How does ML make a positive impact on their business? What examples do they publicly showcase? 

    • What is table stakes to their organization? Do they have a high bar (very largely scaled team), or still learning how to leverage this in their company? 

Without knowing this, or coming in with a hypothesis, it will be difficult to build a compelling business case around your technical win, even if your champion loves your product

Who are we talking to (Name, Link to LinkedIn, Title)

• You’d be surprised how often people skip detailed preparation going into a call. You want to know more about this person. Their motives, who else they know, and most importantly, where they fit within the organization. Are they likely influential, a user, a buyer? How do you know?

Relevant Roles on their Job Boards

• If the company is actively hiring for a relevant position you would need to sell to, do some additional research: 

  • Is there anyone at the company with the relevant experience I need to sell to yet? Else, am I selling to a company working on a new or existing initiative? 

• Job boards and job descriptions tell you so much about a company: 

  • What they’re looking for and why

  • Vision and forward outlook on the company

  • Tech stack (if they don’t support your tech stack, how much is this work pursuing?) 

  • Types of people who are a fit for the role (are they typically the type of person you need to get a deal done?)

  • (Occasionally) the hiring manager. This sometimes signals the buyer or the more influential stakeholders you need to sell to 

Their team — who else should we potentially talk with?

• Do some digging on LinkedIn after you learn the above – you’ll be surprised what you find! 

  • You’ll often hear folks encourage “multi-threading,” which is always an important part of driving sales cycles, but you should know or have a strong hypothesis on who these folks are to get in-roads to 

Goals of the Call

• No goals, no outcomes! Come in with a plan

Good luck out there!

Why “starting with the buyer” is typically a failure mode for startups

“What does my team think,” is what every good executive will ask. You must build trust with developers and the end-users of your product to win deals. You need the technical win first, and then the sales prowess to translate that into a compelling business case. 

“While they may not hold the final decision-making power, their influence has grown exponentially. Today's developers wield significant sway in the procurement process, acting as key influencers who can make or break a deal.”

“We just need to build pipeline” 

Your community and users are your untapped revenue potential. You need to engage them correctly in order to justify how to build real revenue and real pipeline. This takes time and likely the requirement of new skill-development in your company. 

“The evolution of DevRel into the more robust Developer Marketing approach is intrinsically linked to broader economic shifts. The era of zero interest rates fostered a climate where DevRel teams could operate without strict revenue-related KPIs, focusing primarily on community building and engagement. However, as economic realities have shifted, new times called for a more revenue-focused approach. Companies like PlanetScale and MongoDB recently restructuring their DevRel teams to re-align their focus on measurable growth goals are other tangible signs that reveal the decline of DevRel in favor of a more attributable approach to developer GTM.”

​​”By harnessing data and AI, companies can now create outbound campaigns that resonate with developers' specific needs and interests, transforming what was once seen as intrusive into a welcome source of personalized support and information.“

Buying ZoomInfo, setting up a CRM first, and mass-volume is a thing of the past

Use Clay, Apollo, Koala and other world class tools to execute on how to outbound to developers. Read the “Developer-Led Outbound, Done Right” section several times and figure out how to use some of the takeaways in your business. 

Now, you may say “we have zero pipeline, or a very small funnel.” That’s okay. Outbounding to developers and technical organizations means researching and finding the watering holes they drink from. You must know what tools do they use, what communities are they in, and how to find your relevant audience coupled with masterful messaging (we say it all the time here that “messaging is strategy!”) Have you tried reaching out to companies who are leveraging the same tech stacks you’ll need them to be on?

We often hear Founders and their salespeople say, 'we’ve met the signer and it’s the CTO.' While it's great that you now have an executive touchpoint, the signer often isn't the person who will be using the product, nor do they care about many of its features. It's rare for software to be evaluated or decided upon through a top-down initiative unless you're offering a solution specifically for leadership, like Salesforce, Workday, etc. One failure mode we see a lot is “we had a relationship with the CTO and they were ready to buy but a disgruntled engineer thinks they can build it themselves.” This very well may be true, but how much time did you spend with the person who would be implementing the software? If it isn’t “a lot,” then you’ll most likely get stalled in most evaluations. When buying software, good executives will always ask “what does my team think?” 

Executives love to be advisors and sherpas, so use them as such. Rather than running aggressive discovery, leverage them as a peer to get their guidance on how to best sell into their organization assuming your product solves a real pain after an evaluation. 

Aim to have the first call 1:1 and start by introducing and explaining your goal for the call: “My goal of this call is to better understand how [their company] may benefit from the problem we solve, which is: [your problem]. Our solution is typically leveraged by [specific end users or departments at companies like X], so what I’m hoping to do is show you what we’re doing for your feedback, better understand from your POV how I should best position my solution for companies like yours, and who is best from your team and company that could potentially benefit from what we’re doing. Does that sound good?” 

This is a disarming way of starting to align at the executive level, building a relationship and leveraging their tangible feedback on how to sell your solution to their organization. By the end of the call, you want to identify and accomplish: 

• Who are the right people to work with, and why? You’re looking for the person whose opinions are most valued in making important decisions

• What is the best way to meet with these people

• What is the best way to collaborate with their organization (slack, calls, async, etc.) 

• Get an introduction (don’t press too hard, but always make the ask. Don’t ask, don’t get!) 

• Ask for their guidance along the way – rather than forcing them to stay in the entire sales process, keep them informed on progress and re-leverage them later in the buying process as you need to secure a contract

When you get users hooked on the product, you can start to prioritize getting the Technical Win, enrolling executives and other folks within the organization to start multi-threading your opportunity, and leverage your Mutual Action Plan without it being awkward or a homework assignment for your prospects/design partners. 

Let us know how this works for you!

A common frustration I hear from Founders is the cost of events or the experience of "spending a ton of money on a booth, getting a bunch of leads, and gaining nothing from it." Like any good workout regimen or diet, success is about consistency. It’s also about being at the conferences where your actual target audiences are. A good example of a "hit or miss" conference is RSA. It’s typically filled with buyers and executives, which can be useful, but not if you need developers to be excited about your product. Black Hat and other conferences that attract people more interested in hands-on work may be a better fit for your needs. Alternatively, you could complement your strategy by attending both types of events to engage both users and buyers.

Note: events are awkward and uncomfortable for both extroverts and introverts. The way to improve upon this is to start doing it more and make it feel more comfortable for you. As you improve this muscle, you’ll also make others around you more comfortable. Awkward is hard, not impossible…! :) 

Events are one of the best ways to build face-to-face connections with customers and prospects and this can be done on any budget. The main goals are to build brand reputation, gain trust, and foster familiarity with your target audience, while consistently following through. You need to be in the watering holes of your target users and buyers as often as possible. Companies like Datadog may now have the largest booth at re:Invent, but even when they were just getting started, they participated in dozens of small-budget events throughout the year. As they saw results, it justified the larger spend.

What we’ll focus on in this post is how to start building pipeline activities to justify attendance for an event and/or how you can start building more rapport with your target prospects. Future posts will break down how to leverage a budget regardless of your company size (you can be incredibly successful with just the purchase of a plane ticket and hotel room near the venue). 

How to start building pipeline with events:

• Find all of the upcoming events this fall and winter where your target users and buyers will be attending

  • First, you should have a sense of who your most influential decision makers are in your sales cycles (the end user, the buyer, or both). If you’re still trying to validate the hypothesis, then find ways to meet with both. 

    • To find people, you should start looking at conferences your audience typically go to. Thanks to ChatGPT, Anthropic, Perplexity, and others, you can now do something as easy as the following prompt to find the right events: 

      • “help me find developer conferences where i'm most likely to find people who would be interested in my software based on my company description: [paste a simple description of your company or past your company URL for reference]” 

        • “This is great. What about if I'm trying to find executives and buyers based on my company description. where could I likely find them?” 

• Create outbound sequences mentioning you plan to be at the conference and asking if they will be there. Share a brief overview about what you do to get the prospect intrigued. You’re aiming to manufacture responses like:

  • “I plan to be there, but not sure of my schedule, we are actually looking for a solution like this, so let’s plan to meet.” 

  • “I don’t plan to be there, but Stephanie cc’d will be joining this year to represent our team. Maybe you two can meet during the event.” 

  • “Our team is not attending this year, but we are actually looking for a solution in this space. Let’s schedule time in the coming weeks for a demo.” 

• Tell your investors and network you’re planning to attend – seek intros, and also piggyback their budgets and events. Most will be willing to help you when you position the ask and do the leg work on who you want to meet with and why (more on this later) 

Things to keep in mind:

• You don’t need a booth. You won’t be at the booth most of the time anyway, so focus on filling your calendar with meetings around the venue 

• Do you need to purchase a conference badge? Debatable. Buy one if you need to talk to people at their booths or where all the vendors are. Else, you can probably schedule all of the necessary meetings without stepping foot in the conference venue itself

• Alternatively, or in addition to the above, find all of the best parties and sign up. Conferences and parties can feel awkward when attending alone, but a good way to take advantage of them is by asking others if they are also attending. This creates another touchpoint and gives people an opportunity to tell you they'll be there if the timing works. Else, they might invite you to join or visit another party. Perfect!

  • Note: Very aware this too can be uncomfortable. It’s why trying to prepare early and handle over email, text, etc. puts you in the position to show up to events and parties expecting to meet others vs. gazing and badges asking “what brings you to this event

• Asking people if they plan to attend a conference is a better way to build a pipeline than asking for a demo. People want to hear from founders and learn about the latest cutting-edge ideas

• Whether digital, remote, or in person, people buy from people. They seek connections with the brands and companies they purchase from, so be the face of your brand to delight prospects

Get out there, start prospecting, and pound the pavement. Events are the way to build your pipeline quickly. 

We see it all of the time that Founders and scaling sales orgs think they have the “security step” covered, until additional topics come up post SOC 2 review, especially when a questionnaire is involved. The great companies like Vanta, Drata, Secureframe and others have helped companies reach compliance faster and provide early-stage and late-stage companies security best practices. That said, there are still a lot of internal steps you can take to ensure you can meet the security standards of your prospects and customers. 

Over the past few years, I’ve constantly shared the SaaS CTO Security Checklist originally created by the folks at Sqreen. It’s still super relevant today but to make this a bit more actionable, we turned it into an interactive Notion doc you can use with your team internally. We’ve also made some refresh changes and additions to this checklist based on guidance from amazing CTOs and Security experts at the best startups in software. 

Let us know what we missed, should include, and how to make this better. We all want to simplify our security step in sales cycles…! 

You can start thinking about offloading your prospecting and pipeline building when:

• Your messaging is working — A CTO (and Founder) of a publicly traded company once told me “Messaging is Strategy” and this is absolutely true. You as the Founder must create and know the messaging and positioning that resonates with prospects. You cannot outsource this or your team will deviate from your value proposition and vision of why you built the company. 

• The “profile” of company and account who fits your product — Yes, you can consider this an “ICP,” but even companies at $10M+ are still learning who their ideal customer is. Focus more on learning the problems, profiles, and desired outcomes of your ideal customers and document them so future hires can follow. 

• There are few surprise objections  — You know how to handle 95% of objections that come up to unblock the mindset or education requirements for a customer to understand the value of your solution in comparison to their alternatives (including no decision!)

• You know how people want to engage with your company and buy from you — What are the steps for someone to want to learn, understand and use your product? This includes when someone asks “so, how much does it cost?” 

• You know your GTM stack — You want to know how all of your systems work rather than hiring someone to think through how to solve things outside of the scope of their role. AEs and SDRs should not be responsible for building systems. 

Note: If you have the good fortune of having a huge top of funnel from inbound leads and/or product-led lead, you still need to know a similar set of the above requirements. The same type of qualification process needs to be learned to ensure you’re building a qualified pipeline this month, quarter, and year.  Having worked with some of the best PLG companies in the world, I’ve seen many teams attempt to offload sales to inexperienced folks with limited enablement which led to a swift “restructuring” down the line.

If you haven’t figured out the above yet, a “young hungry person” is likely set up for failure. They may work incredibly hard, show some early signals of wins, but as the Founder, you are responsible for creating their path to success. You should show a clear path for them to follow vs a “figure it out along the way” mindset. SDRs and AEs don’t know what you know about the market, your vision, and why people will ultimately buy your product. You’ll start to see how stark of a difference their knowledge of objection handling in your market is as you hear the basics being missed – this is normal and why enablement, training, and front-line management exists in sales. If you have none of that yet, you must be incredibly cautious of who you hire and how you offload such an important part of your future revenue streams. 

From experience, we feel more strongly about hiring a qualified Account Executive as your first hire who can run full-funnel sales. With the above, if you feel good about your pipeline building process, you as the leader of your revenue efforts can decide which areas are your biggest bandwidth constraints. 

What about outsourcing to experts? 

An outsourced firm never works for early stage companies. They really only “work” for transactional products (non-technical fast sales-cycle SaaS) and/or when they are following a color by numbers framework that you expect them to follow and not deviate from the script. Even then, you are losing full control over the most important lifeblood of your business: the pipeline that allows you to hit your revenue goals. 

There are clever and great approaches outsourced firms take but you should own your pipeline. Rather than outsourcing outbound, learn best practices on how to build pipeline the modern ways through resources like Clay University, Koala University, and other best practices shared from companies like Apollo. 

Get started now, it will take you no longer than 2 hours to start owning pipeline building:

• Work on your outbound messaging – you need one value prop email with two reasonable follow ups. It will not be perfect. Just get started (1 hour)

• Think about subject lines that align with your value proposition  (10 minutes) — Why this matters: as you start outbounding, you can see which titles are willing to engage with your email regardless of response. For example, if VPs of Engineering are consistently opening your email 50% of the time and not responding, you know your “hook” works, now you must figure out what will initiate the response. 

• Set up an Apollo account (10 minutes)

• Build your first prospecting list (20 minutes)

• Set up your sequences with your messaging (10 minutes) — Bonus, strong recommendation: Add LinkedIn outbound to your sequences and/or use LaGrowthMachine (extra 15 minutes)

Review your results daily (block 10 mins)

• Review the metrics and performance of your campaigns daily 

  • Open Rates

  • Reply Rates

  • Profile reviews: 

    • Who is opening (titles, company size, etc)

    • Engagement per profiles (any surprises?) 

  • Which subject lines and emails perform better than others?

    • Anything that signals where you should double down? 

• Share the results with your team

  • Seek feedback, share reactions, learnings so the team feels enrolled and wants to help participate

  • Prospecting is a team sport! Get your team involved – it’s fun and an incredible way to grow your business as you start to learn what works. Enroll your leadership and get going. You can also leverage your investors in a more effective way too :)

Maybe you’re already doing this and still feel strongly you need to take this off your plate. If you feel like you’re doing the above well and won’t need to coach someone step by step through the process daily, then start thinking about who you’re going to hire that can do this exceptionally well and can see very similar results quickly. 

Note: Do not give up. It takes 6+ months to see signal of effective repeatable pipeline growth. Experiment every week. Don’t rotate too much on too many experiments at once. Pipeline building is like dieting – you won’t see results unless you’re consistent. 

One piece of advice I often see is asking your customers, “Why did you buy, and what were you hoping to accomplish?” If you are asking this after the purchase, you’re already behind. This is not a best practice for a startup at the early stages. This advice is more suited for a new leader or account owner at a scaled organization where the data about the customer is scattered or you’re seeking clarification on specific topics that need further validation.

In the spirit of this post, we’ll assume you know the following about your customer. If not, you know where to start before the rest of this post is relevant!

• What does the customer do? – What is their business model, and how do we impact it?

  • Most obsess over “ICP,” but don’t think about why your solution matters to their company. If you are an AI company, you should know how your model allows their business to do something mission-critical. Otherwise, why would they stay next year?

• Why did they buy from you compared to their alternatives?

  • Why this matters: Aside from the obvious reasons, you should assume that even after winning the deal against a competitor, the competitor isn’t going to relent. No competitor? Someone will come after you eventually (including the disgruntled user who thinks they can build an alternative)

• Why did they buy now instead of later?

  • Why this matters: “Compelling event” or “urgency” is usually the sales meme that justifies a purchase. That said, if the customer needed it for something this year, but it was a one-off case, do you have a clear line of sight on how you’ll retain this customer next year?

• What was the deal value ($)? 

  • Why this matters: Did they underbuy or overbuy? Not sure? You want to make sure, at the very least, you can retain the revenue that is equivalent to the perceived value at purchase. Otherwise, you’re going to be in a tough spot come renewal time

• Who signed the agreement? 

  • Why this matters: You should always know who signed the contract. Most of the time, people think they know, but I’d encourage you to review each of the contracts your customers have signed in the past 12 months and check if you have a relationship with each signer. Remember, you are the CEO. The executive who signs is your peer.

• Who owns the account on a daily basis? 

  • Why this matters: You need to know who is going to request the budget next year. Additionally, you want to be careful about what happens if this person leaves. Do you have anyone else who is an advocate? Often, you’ll hear the recommendations of “champion development” and “multi-threading.” This is why it matters post-purchase as much as it matters pre-purchase.

What we see often is that Founders have an “oh shit” moment when they realize a renewal is coming sooner than they realize. Timing and bandwidth is difficult, but I promise trying to find another customer in place of a churned one is far more painful than proactive management. 

On a more positive note, some Founders are still in survival mode worried about winning customers, forgetting how much better their product has improved over the past 3+ months. They’re too close to the day-to-day of building and are pleasantly surprised when they try to position upsells. 

How do you know when you’re in retention mode or growth mode? Start with this frame of reference. If you can’t fill this out confidently, start reviewing with your team how you can start to gather this information for each customer. We encourage you first prioritize renewals in the next 90 days, but over time you should be able to review each customer with this level of detail on a weekly basis: 

• Customer

  • Name of Customer

  • Who we are working with

• Renewal Date

  • Prioritize annual contracts, if you are still an MRR-driven business, prioritize the companies that matter most to you from dollar amount and “logo value” (ie your lighthouse accounts)

• Deal Amount

  • Straightforward

• Customer Health

  • Prioritize product adoption and active usage as the most important metric

    • Are people using as expected? 

    • Have there been complaints or walls being hit in slack? 

    • Happy or unhappy customer? 

  • Do they use the product for what was discussed pre-purchase? 

Recommendation: Use PostHog, LogRocket, or something similar to monitor usage and actual sessions to ensure customers are using the product as intended. You can typically catch potential issues you would have missed without a phone call or asking specific questions. 

• Likelihood of renewal

  • If their contract renewal were today, how confident are you they would renew? 

• Upsell potential?

  • Are they using all of your features? 

  • Are they hitting the growth goals you set together? 

  • Are they using your service a ton but “underpaying?” This is super common, talk about it amongst your co-founders and/or leadership team and put together a plan to discuss upsell plans with a customer. You’ll be surprised by what you can come up with :) 

• Technical Blockers/Risks

  • Your product isn’t perfect (It’s fine if your product isn’t perfect!!).  But you should know where the customer has expectations or requirements in order to get more value or meet their expectations in order to renew. This should be your main obsession and balance on where time allocation goes in regards to your product roadmap. You can also leverage this to identify “is this a good customer for us based on what they expect and what we can deliver?” 

• Contractual Blockers/Risks

  • Some customers share their contractual concerns (usage, cost, etc.). Have you gotten ahead of any potential concerns? 

  • Do you have access to the person who owns the product? The signer? 

    • Is there a new signer this upcoming year? 

    • Do you have buy-in from all the relevant stakeholders? 

• Next Steps

  • Have someone own the next steps and touchpoints with each customer based on the topics above. Share the ownership amongst the team vs. shouldering it all yourself. Make this a team sport! Helpful resources include Mutual Action Plans and Close Plans (these apply to post-sales efforts too)

The above will help you have a much more productive revenue-focused conversation about your customers. Your Engineering and Product leadership teams may already talk about some of the technical needs and capabilities, but this allows you to have a more holistic view of what will impact your revenue streams on a consistent basis. 

Here’s a template if you need one.