Author Archives: Ayala Ples

  1. Building an outbound sales motion

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    This is the third in a series of articles based on “Crane Foundations”, an instructor-led course on how to build founder-led go-to-market, originally created for early stage B2B companies in the Crane portfolio.



    As a founder, a strong indicator that the time is right to start testing an outbound sales campaign is when you are unable to generate enough opportunities from either your inbound leads or your bottom up motion.

    Defining “who”

    The first step when embarking on any outbound sales campaign is to define your target market.  

    This is a list of companies and individuals that you want to get meetings with so you can try and validate your Ideal Customer Profile hypotheses.

    Including companies of different sizes in your target market is a good idea as it helps with this validation and also maximises your chances of hitting your revenue goals.

    Once you have compiled your initial list of companies, the next step is to identify potential Economic Buyers and Champions using something like the Miller Heiman model.

    Aim to identify multiple people per company to get meetings with, with 200 to 400 individuals being a realistic amount to compile without needing much additional help. 

    A typical outbound campaign will contain a much larger number of individuals than 200 to 400, but for an initial outbound test, this number should be sufficient.


    The campaign “how”

    Having compiled your target market and the list of who you want to get a meeting with, the next step is to work out how to get in front of them.

    This stage of an outbound campaign can be frustrating for founders as it often feels like they are hitting a brick wall of unresponsiveness.  This is quite common, so the first type of outbound campaign we will look at is one designed to address this common frustration.


    The power of introductions

    The goal of an introduction campaign is to replace the brick wall of unresponsiveness by asking for introductions from people in your (and your co-founder’s) network who have direct connections to your targets, or at the very least to someone who might be able to get you in front of the target person.

    As with every other part of the sales process, getting an introduction needs to be a managed activity, with message personalisation and follow ups being tracked and measured. To make this more manageable you might want to consider starting with just the top 50 most important prospects from your target list. 

    List of persona types

    Figure 1: Introduction Campaign tracking spreadsheet

    Whilst it is by no means a “silver bullet”, an introduction campaign can be an effective shortcut to getting meetings with the right people and closing some early deals. 

    However, you should keep in mind the following tips to ensure that the campaign has the best chance of success –

    1. Ask for specific introductions from specific people. The main reason introduction campaigns fail is because founders ask potential introducers something broad like “do you know someone at this company or in this industry?”. The key to success is to ask for introductions from specific people to specific people. As you will likely be using LinkedIn for your preparatory work, keep in mind that potential introducers are often connected to people they do not really know so try to identify several people to ask for a particular introduction.
    2. Send them some sample text they can use. If someone in your network says that they can make an introduction for you, be sure to send them some sample text, making sure the text is clear about –
      1. What your ask is 
      2. What the benefit would be for that person to speak with you
      3. Avoid filling the sample text with what you do. Instead, describe the problems you are looking to solve. Also ask the introducer to keep you copied (cc’d) into the introduction from the start.
    3. Keep the introducer in CC. If the prospect responds to the introduction, put the person who made the introduction into CC (not BCC) until the meeting has been booked. This may sound counterintuitive but our experience shows you will get better and quicker responses this way.
    4. Use use of your investors for introductions. Investors are often very well connected but underutilised by founders as a source of introductions. Using part of every board meeting to go through a list of introductions, allocating approximately 10 per investor can be very effective (so long as you make sure to follow up with them regularly).
    5. Ask existing customers for introductions. If you plan to ask any of your existing customers for an introduction then it is important to do this in person as these introductions are much more valuable but also more sensitive to ask for.


    Example emails

    The following example can be used as a template to ask for an introduction. Be sure to include LinkedIn profiles of the people you want introductions to to make things easier for the introducer –

    Hi <name>, 

    I noticed you’re connected to the people below and I’m hoping you might be able to introduce me?

    • Person 1 <LinkedIn profile link 1>
    • Person 2 <LinkedIn profile link 2>
    • etc…

    We’re trying to get introduced to as many people in the roles as we can to ask them for 15 minutes of their time to get feedback on what we’re building. 

    Do you think you’d be able to make an intro to any of these people? I can provide some text about us if you’re happy to make any intros.

    Many thanks


    Example email 1: Asking for an introduction

    If they are open to making the introduction for you, you can then send them something like the following. Again, make sure it is not a description of what you do, but is a succinct and compelling summary of the business value you deliver to the person you want to meet with.

    Hi XXX,

    I hope you’re doing well. 

    One of the companies I work with / <or description of how you know them> has asked if I can make an introduction to you. 

    They have a solution in your space aimed at solving <problem X> and delivering <value Y> and would like to get some feedback on it – they’re asking for 15 minutes of your time.

    I thought you might find it interesting to hear about what they do and have included a short paragraph describing it below.

    Let me know if that would work for you?

    Many thanks



    Example email 2: Sample text for your introducer

    Introductions tend to deliver much higher rates of meetings than any other outreach method so it is worth trying to drive as much value out of your and your co-founder’s networks as you possibly can.


    Cold outreach

    A cold outreach campaign is when you are trying to reach people that you do not have any connection with.

    Email, LinkedIn, webinars, events, direct mail, online communities and phone calls are just some of the myriad of channels available for cold outreach. 

    We will focus on two of the most common and readily accessible ones for this kind of campaign – email and LinkedIn, but you should expect that a given person will need several prompts across a number of different channels before they respond.

    Regardless of the channel and number of prompts, the most important thing for making any cold outreach campaign successful is personalisation.


    Keeping it personal (emails)

    When crafting a personalised cold outreach email, keep the following tips in mind to maximise your chances of getting a meeting – 

    • Subject line.  Personalisation begins with the email’s subject line. If your recipients do not like the email subject they are very unlikely to open your email. There is no way of telling what subject line will work until you start testing options so it is important to be able to measure email open rates using platforms like Hubspot, Apollo, Salesloft, Outreach etc . Ideally, you are looking for a minimum open rate of 50%, with 60% or above being ideal.
      • Emails with generic subject lines tend to get deleted without being opened, so personalising it to the particular persona and keeping it short (5 to 6 words at most) tends to lead to better results, as does picking out a short phrase from the body of your email and using it as the subject.
    • Email body. As with the subject line, everything about the body of your email needs to be tested and iterated on to find what really works. The following guidelines perform consistently well and should help you to get started –
      • Keep the email to 3 short paragraphs followed by a clear call to action
      • Get to the point quickly and keep the total length of the email to 150 words or less
    • Paragraph 1. Many email clients preview the first few lines of an email, so your opening paragraph, together with the subject line, has additional work to do in order to get their full attention such that they open and read the entire email.


    The best way to get their attention is to personalise the opening paragraph to the specific person you are contacting. However, try and avoid this form of generic personalisation –

    Hi <name>

    I can see that you’re <Role> in <Company Name> so I’m sure you care a lot about <This Problem>.

    This type of opening paragraph will likely result in no replies (and may very well end up getting filtered as spam). Instead, try to focus on creating something truly personal to the recipient – 

    Hi <name>,

    Congratulations on the merger with ACME. You and William have built a great company and it’s good to see XXXX becoming the largest <their industry> company in Europe.

    This type of personalised first paragraph has clearly been written specifically for the recipient and demonstrates the sender has done some research about them and the company they work for.

    • Paragraph 2. If the first paragraph is designed to get your prospect’s attention, then the second paragraph has to tell them what is in it for them. 

    You can do this either by highlighting the pain that you solve or by showing the value you provide to the person you are emailing. 

    Again, this should not be a description of what your company does, it should be what’s in it for them specifically to engage with you further in order to find out more. 

    • Paragraph 3 is about showing the relevance to them and their company along with some “social proof” – real examples of the value you provide that demonstrate you can deliver what you say you do.
    • Call to Action (CTA). The final part of the email should be a clear call to action which in most cases will be a request for a quick call.


    Tying it all together

    Subject: Your Recent Merger With ACME

    Hi <Name>,

    Congratulations on the merger with ACME. You and William have built a great company and it’s good to see <their company> becoming the largest <their industry> company in Europe.

    When I talk to operations leaders like you, there is one question that ALWAYS comes up: how do I make sure that all my onboarding, claims and maintenance processes are on track and completed on time, with excellence?

    I’m asking because we recently helped <competitor>, in the first month, to automate 9 out of 10 steps of what used to be an entirely manual process, dramatically decreasing turnover time and improving the quality of their operations. 

    Do you have 15 minutes to explore this further in the next week?


    Example email 3: a good personalised outreach email

    Personalisation and outreach volume are inversely proportional, so this level of personalisation should ideally take no more than 5 – 10 minutes per email, otherwise you will not be able to send enough emails to be effective. 

    It is also why it is important to continually run rapid iterative outbound tests to identify the right level of personalisation and message content that delivers the greatest response rates with the minimum of effort.


    Keeping it personal (LinkedIn)

    In our previous article on managing inbound sales we recommended sending LinkedIn connection requests without a note.  

    Although this sounds counterintuitive, especially in light of the importance of personalising messages, we generally see higher acceptance rates when the connection request does not contain any additional information.

    If the connection request is accepted, then the same personalisation for emails applies to your follow-up message and, as with emails, if the follow up message is not relevant to the person or their role you are unlikely to get any responses.

    Personalisation is more challenging with LinkedIn as your message needs to be very short, ideally no more than 50 words (or about a third of the length recommended for a personalised email).

    This is why you may want to consider experimenting with LinkedIn Voice Notes and include a 30 second voice recording to your outreach sequence for your follow up message.  



    Whether you are running an introduction campaign or doing cold outreach, it is important to define what your outreach sequence or cadence will look like.

    The “Agoge” sequence pioneered by Sam Nelson is a great way to track your outreach cadence as it is designed to maximise your response rate while minimising the personalisation work required.

    Figure 2: A reduced Agoge sequence

    A full Agoge sequence includes 15 outreaches or “touches” over a period of 27 days so is best suited to larger companies that have dedicated lead generation teams.

    A reduced Agoge sequence like the one in Figure 2 is therefore much more appropriate for an earlier stage business as it only requires 3 personalised messages, two of which can be based on the research conducted for the first personalised email in the sequence.

    There is no ideal outreach cadence, so just as with every other aspect of running an outbound campaign, as a founder you will need to track and test different aspects to see what works. For example, over time you may realise that you need to have different sequences for different priority prospects.


    Metrics that matter

    For any personalised outreach, founders should aim for an average open rate of over 50%. Anything below indicates you need to start testing different subject lines or the initial 10 to 20 words of the first paragraph. 

    If you are seeing open rates of 20% or lower, then it is highly likely that some of your emails are getting filtered as Spam.

    In terms of getting responses to your personalised outreach, a response rate per sequence of over 10% (with the majority of these being positive responses) and a meetings booked average of over 5% per sequence is what you should be aiming for.

    And to reiterate, in order to get anywhere close to these metrics you will need to personalise your messages and use multiple channels.


    A final word: enrichment

    Once you have compiled your initial target market and identified an initial 200 to 400 people, you may need to do some additional enrichment to gather more complete information about them to support your personalisation efforts.

    Tools like Zoominfo, Cognism, Apollo, Lusha and Hunter along with a multitude of others are available, all at various different price points. Our experience has been that a single tool is rarely enough and a combination is usually required to get a complete set of information about your potential prospects.

  2. The 4 steps to managing inbound sales

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    Ben Wright on the 4 stages of managing your inbound sales motion


    This is the second in a series of articles based on “Crane Foundations”, an instructor-led course on how to build founder-led go-to-market, originally created for early stage B2B companies in the Crane portfolio.



    As a founder you will almost certainly need to employ a variety of different sales motions throughout the lifetime of your start-up, so in this and the following article in this series we will be covering how to manage the most common ones, starting with an inbound sales motion.


    Sales repeatability recap

    In our previous article we covered why, regardless of whatever sales motion you adopt, the key to sales repeatability lies in a founder being able to identify an initial beachhead ICP market.

    As you embark on finding this market and establishing your initial go-to-market motion, you can be fairly certain that any early hypotheses you have developed on who is most likely to buy from you and be successful will either be partially or completely wrong.

    This is very common and part of the normal process of establishing product market fit.

    It is also the reason why, as a founder, it is important to embrace the idea that identifying markets that you can sell into successfully is a never ending process of iterative testing.

    Even if you happen to get lucky and establish some early sales repeatability, it is very unlikely that that initial motion will work the same way in six or twelve months’ time because as your start-up evolves, so does the market.

    This is why the process and steps described in Figure 1 continue to apply even when you scale to tens of millions in revenue.

    Figure 1: The continuous iterative process of testing markets


    • Step 1: You develop a hypothesis about who is most likely to buy from you and test it by getting as many meetings as possible with prospective customers.
    • Step 2: You test every part of this hypothesis rapidly, from your outreach messages and communication channels, call scripts, meeting agendas, discovery questions, demos, stakeholder engagement, value proposition etc. 
    • Step 3: You rigorously measure the effectiveness (or not) of every aspect of your testing, such as email open and response rates, the number of meetings booked, through to the number of demos delivered, how you have gained access (or not) to important stakeholders and ultimately the number of won and lost deals. 
    • Step 4: You review what you’ve learned, keeping what works, and stopping what doesn’t and then go back to Step 1 to begin testing your next hypothesis. 

    And most importantly, you should embed this process into the way you operate right now, even if you are the only person doing the work, because it will ensure that your Go-To-Market (GTM) motion continues to be fit for purpose as you scale.


    The goal of every sales motion

    Whatever sales motion you begin with or adopt over time, the goal of each of them is the same: to generate meaningful revenue*, with the first and most important step to achieving this goal being to secure meetings with the right people.


    As a founder, you are likely to encounter a variety of different people or personas in your sales meetings, so being able to identify them and understand their role in the buying process maximises your chances of securing meaningful revenue.

    Understanding buyer personas also helps make effective use of your (and their) time and effort.

    The Miller Heiman model provides a simple way to categorise four key personas you are likely to encounter in these meetings –

    • Economic buyer (EB) – this is the person who actually owns the budget to pay for your solution and will normally have the final sign off. The level in the organisation hierarchy where you will find your Economic Buyer depends on the price of your solution, as budgetary sign-off authority varies from level to level, and from company to company. A common mistake is to assume that the person you are speaking to in a sales cycle is an Economic Buyer, when the true EB is actually higher up in the management hierarchy.
    • Champion (C) – a Champion is not just someone who is enthusiastic and will advocate for purchasing your solution, they also need to have sufficient authority and / or influence to get you in front of the Economic Buyer. Your goal when meeting potential Champions is to build trust by helping them understand the value you can bring to their company, department and to them individually. If done correctly, they will become a Champion and actively advocate for your solution internally, bringing or introducing you to the right people. Common pitfalls to avoid are believing your Champion is the Economic Buyer when in reality it is likely to be their boss (or even their boss’s boss), and to assume their enthusiasm means they also have the necessary authority or influence.
    • User Buyer (UB) – this is typically the person or group of people who will use your solution day to day and evaluate it based on their user experience. User Buyers often contact you directly (“come inbound”) as they are actively looking for something which makes their own work easier. If you offer an open source, freemium or free trial version of your solution it will invariably be User Buyers that download it or sign up. A common pitfall with User Buyers is to mistake them for a Champion because they are often very enthusiastic about your solution. No matter how much they love what you do, if they lack the authority or influence to help you navigate the business and get in front of the Economic Buyer, they cannot be considered a Champion. User buyers are also the persona most likely to visit your website and although you will have to work hard to navigate from them to a Champion and then to an Economic Buyer, engaging them can often be a great source of learning and information for you (assuming they are willing and able to introduce you to a potential Champion).
    • Technical Buyer (TB) – this person or group evaluates whether it is feasible or safe to implement your solution. They can be from IT or Information Security, or could also be from Legal, Finance or Procurement. A Technical Buyer could veto the purchase of your solution for any number of reasons so it is important for you to understand who the Technical Buyers are and to engage them at the right time in the buying process.  

    Now that we have covered the kinds of personas you are likely to encounter in a sales process, for the remainder of this article we will take a look at managing an inbound sales motion**.


    Capturing details

    An inbound sales motion is one where prospective customers have contacted you, usually by interacting with your website in such a way that you are able to capture details about them and their company. 

    Downloading gated content, asking to be added to a waitlist, requesting a demo or signing up for a free trial are just some of the ways to capture details on inbound leads.

    With your limited capacity and resources, capturing the following details allows you to efficiently prioritise inbound leads for further engagement, with any leads that are a match (or close match) to your ICP hypothesis being the highest priority – 

    • Name 
    • Company
    • Work email address
    • Phone number (optional)

    Whilst most inbound leads will not leave their phone number, any that do are likely demonstrating that they have a high degree of interest in your solution. Once you have done some research on the person and their company, if they turn out to be a match or close match to your ICP, you should not hesitate in picking up the phone and speaking with them. 

    Also, depending on your solution you may also want to consider capturing their role and/or department, however it is the company they are from that is the most important detail needed for prioritisation, hence why you should mandate a work email address. 

    Without knowing what company they are from, it will be impossible for you to prioritise your inbound leads which increases your risk of spending precious time and effort on leads that are unlikely to yield any meaningful revenue.

    Figure 2 describes the flow and steps of a typical inbound sales motion with the ultimate goal being to maximise your chances of generating meaningful revenue by securing meetings with the right people. 



    Figure 2: Inbound lead to meeting flow


    • Step 1: Examine the details captured to determine if their company is a match/close match for your ICP, and use the company and person’s name to determine their role, using the Miller Heiman model to categorise them as either a User Buyer, Champion, Technical Buyer or potential Economic Buyer.
    • Step 2: Having compared the inbound lead to your criteria for an ideal company and persona, triage it into High, Medium or Low priority.
    • Step 3: For anyone you have determined to be a low priority lead you can send them an automated sequence of emails focused on helping them get the most out of your solution. If they have signed up for a free version or free trial then directing them to more online content may work better then sending emails. Low priority leads might include people you cannot identify or people who work at companies that are not a fit for your solution. 

    Medium priority leads could be people from a company that matches your ICP  but the person is not necessarily your ideal persona. In this case putting them into an automated “nurture” sequence of emails and LinkedIn messages where you send them product details interspersed with an occasional personal outreach asking if a meeting might be of interest works well. If you do not have many high priority leads it is also worth considering doing a more personalised outreach instead.

    High priority leads are a match/close match to your ICP. If you offer a free signup or download, check to see if other people from the same company have also signed up / downloaded as that could be an indication that a broader evaluation of your solution is taking place. Regardless, for anything you have determined to be high priority, you should spend some time researching the company, person and any mutual connections so you can send them a highly personalised outreach email or LinkedIn message suggesting a meeting. You also want to reach out to them as quickly as possible because there is a strong chance they will also be looking at your competitors and the company that engages with them first will often set the agenda for everyone else.

    If your volume of inbound leads is low you may want to consider a broader set of prioritisation criteria to optimise for more meetings.

    Conversely, if you have a high volume of inbound leads you should consider stricter prioritisation criteria to make the best use of your limited time and resources.

    The important thing to note is that the key to making an inbound sales motion work is to have a clear strategy for how you want to prioritise, categorise and engage with each inbound lead.



    The goal with high priority inbound leads is to engage them in a meeting for deeper sales discovery, so it is important to reach out to them with a highly personalised message as quickly as possible (within 2 hours is a good target to aim for).

    Research their company and the person and try to find something that will demonstrate your request for a meeting is not a generic message, and that you are a real person reaching out to them specifically.

    If you offer a free trial or freemium product that they have already signed up for, then including some details on their usage can also be a very helpful way to personalise your message.

    You should also consider using a variety of different channels to engage your high priority leads. As previously mentioned, if they have provided a phone number then you should aim to call them right away, otherwise connecting and messaging them on LinkedIn as well as sending a sequence of personalised emails works well (counterintuitive tip: sending a LinkedIn connection request without a note tends to have a higher acceptance rate). If they accept your connection request, think about sending a LinkedIn voice note as part of your outreach as they are intrinsically personal and often very effective.

    If you are targeting developers, emails are unlikely to be successful, but LinkedIn and engaging them in Slack or Discord developer forums should yield better results. 

    Even though they have “come inbound”,  do not be surprised if it still takes multiple outreaches across different channels to elicit a response from high and medium priority leads (we recommend trying a minimum of 4 outreach attempts).

    Depending on your volume of high and medium priority leads, multiple outreaches across multiple channels could be a lot of work so if you are getting a 100+ high priority inbound leads a month, engaging a team member or hiring an intern to help filter or “rinse” the inbound leads can work very well. 

    The important thing to remember if you elicit someone’s help is that any outreach must look like it is coming from you the founder, so you should consider setting up an additional email account and grant them access to your LinkedIn to send messages on your behalf – just remember to always approve the content they are sending.



    In the next article in this series we will look at building and managing an outbound sales motion along with examples of effective outreach messages, but for now, the four key steps to successfully manage an inbound sales motion are –

    1. Capture: as much as detail as you can about your inbound lead
    2. Compare: that detail to your ideal customer profile
    3. Prioritise: triage, prioritise and engage each inbound lead based on a clear strategy 
    4. Personalise: research your high priority leads and reach out to them quickly with a highly personalised sequence of messages across multiple channels


    *Meaningful revenue = in the tens or hundreds of thousands per deal

    ** An outbound sales motion will be covered in the next article in this series

  3. Launching “Crane Foundations” with “The key to repeatable sales”

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    Ben Wright on finding your narrow ICP


    This is the first in a series of articles based on “Crane Foundations”, an instructor-led course on how to build founder-led go-to-market, originally created for early stage B2B companies in the Crane portfolio.

    The counterintuitive “why”

    As the founder of an early stage start-up who has raised, or is looking to raise an initial funding round, a large total addressable market (TAM) worth billions of dollars has no doubt been a part of your pitch to investors.

    Post securing initial funding, the natural inclination of many founders is to try and concurrently sell into as many different companies, industries and geographies as possible within that large TAM.

    This seems logical, especially if your product is applicable across multiple industries, companies and personas.

    The reality however is that the software industry is littered with thousands of start-ups who tried this approach and failed because they ended up spreading their limited resources too thinly and ran out of money before they could develop any kind of sales repeatability.

    A lack of sales repeatability is one of the most common reasons start-ups fail to raise their next funding round and / or ultimately fail as businesses.

    This is why the approach of nearly every successful start-up has been to avoid trying to sell to everyone and anyone in their TAM, and instead (somewhat counterintuitively) begin by focusing on a small subset of the market before expanding further.

    The foundational “what”

    Founders who have successfully built sales repeatability did so by relentlessly working to identify this small subset or Ideal Customer Profile (ICP) market.

    In practical terms, identifying this ICP market is a process of working out –

    Who is most likely to buy from you and be successful, so you can focus all your resources on selling to them

    The answer to this question invariably involves a lot of hard work, testing and iteration, but remaining relentlessly focused on it has immense benefits which we will cover in more detail later.

    The iterative “how”

    As an early stage founder, you probably have some initial ideas about who is most likely to buy from you, however don’t be surprised (or disheartened) if your initial hypotheses turn out to be partially or even completely incorrect.

    This is very common, so the goal is to test your hypotheses quickly to determine if your proposed ICP market contains –

    1. People who have a real “hair on fire” pain, and are willing to pay in order to solve it. This is the single most important part of identifying your ICP market.
    2. A single, identifiable economic buyer who has access to a budget (and sufficient authority to divert some or all of it away from other areas if needed).
    3. People who are happy with a “complete enough” solution, i.e. one that addresses the immediate pain sufficiently, without necessarily having all the functionality of a “complete” solution.
    4. No dominant incumbent. Competition in any given market is to be expected, however if your prospective ICP market already has a de-facto owner, you are unlikely to find much success here unless your product is demonstrably 10x better and/or 10x cheaper.

    The next step in testing a potential ICP market is to secure as many discovery meetings* as possible with people you believe match these criteria, using each meeting as an opportunity to discover more about their specific pain and your ability (or inability) to address it.

    It is important to keep in mind when meeting that it is not your definition of the pain that matters, but rather the prospective customer’s. If there is a mismatch, or if they are unaware or do not care enough about it to pay to solve it, then this is unlikely to be a successful ICP market for you.

    A pattern should emerge relatively quickly from these meetings about whether this proposed ICP market is a suitable candidate, or if it’s better for you to concentrate your limited time and resources elsewhere.

    Beachhead benefits

    A useful way to think about your ICP market is as a beachhead — a secure foothold in part of the larger market where you can build some initial success before expanding further.

    Even with seed funding you are still likely to be resource constrained, so this beachhead needs to be small enough for you to have a chance of winning, but large enough to service your short to medium term revenue needs**.

    Focusing on a beachhead brings significant operational benefits that would not be available if you were attempting to address the entire market at once. These include –

    • Increased network effects — in a beachhead market, people tend to know other people working at similar companies. This makes referrals and introductions easier as word of mouth amongst peers speeds up the process of getting in front of the right people.
    • Increased expertise — a beachhead helps you develop specific expertise about what potential buyers really care about, and more importantly what their specific pains are. This learning means you are able to demonstrate a deeper understanding and competence with prospective buyers which should help you to close more deals.
    • Improved content — content creation and targeting becomes simpler as it is tailored for specific buyer personas, resulting in better quality leads. Similarly, product marketing materials, case studies, and other sales collateral can be tailored for the beachhead to achieve maximum effectiveness.
    • Improved outbound campaigns — a beachhead allows you to focus on quick A/B tests of outbound messaging, landing on what works in a much shorter time frame than if you were trying to address the whole market.
    • Improved digital marketing and events — marketing campaigns and events can also be more targeted and effective as they are now based around messaging that is specific to the prospective buyer’s pain.

    These benefits make the best use of your limited time and resources and compound over time, resulting in your sales process becoming increasingly efficient and repeatable and eventually leading to a more stable and predictable revenue footing.

    Finding the beachhead

    The following variables provide a good starting point to narrow down from your large TAM to an initial beachhead or ICP market –

    1. Industry — are there particular industries where you believe there could be a significant pain that you can address? An industry focus has advantages because if you are able to secure some initial deals, other prospects should prove easier to engage as they will only really be interested in what their industry peers are doing.
    2. Geography — are there particular geographies you believe could have a significant pain or a better understanding of the pain? Or, where competition is weaker or non-existent? A geographical focus does have practical considerations, including time zones, language, business culture and travel requirements so focusing closer to home until your ICP is better understood may make more sense.
    3. Company profile — is one the most common variables used to find a beachhead. This could include the size of the company by revenue or number of employees.

    Whilst these provide a starting point, it is really important that you also consider any specific variables that are relevant to your solution, such as –

    • Use case — are there specific business problems or workflows that repeatedly resonate because of the pain they cause?
    • Technology stack — are companies that are using (or not using) particular technologies more likely to be experiencing a pain you can solve?
    • Regulatory requirements — are specific companies or departments subject to regulatory pain? And are there particular geographies where that regulatory pain is more acute?
    • Specific departments — are companies with (or without) a specific department more likely to be experiencing a relevant pain? Or, are departments of a specific size relative to the overall company size an ideal target?

    Finding the right mix of specific variables is your ultimate goal, and the more granular you can be, the greater clarity you’ll have about whether the ICP market is suitable and which types of people and companies to target.

    Company size considerations

    Company size is a particularly important facet of the company profile for you to consider because the buying processes, complexity and length of sales cycle vary greatly between companies of different sizes.

    Segmenting companies by size is particularly helpful in determining where you may have the best chance of initial success. For example –

    1. “Rabbits” — are the smallest size of company you would consider selling to. Whilst the deals may not be large, they will typically have shorter sales cycles and fewer people involved in the buying process. Rabbits can usually go-live and demonstrate your product’s value quickly, providing valuable feedback and insight. Some companies in this segment may also punch above their weight in terms of brand recognition, providing more credibility with other prospects.
    2. “Deer” — are mid-market companies which have the potential to deliver larger size deals than rabbits. These types of companies can have huge variability in terms of early adoption, so it’s important to assess if there is early adopter behaviour amongst individuals involved in the buying process. As deals will likely take longer in this segment, assessing how “hair on fire” the pain is becomes even more critical.
    3. “Elephants” — are larger, often global companies that have huge revenue potential but are typically harder (and take longer) to win because they have complex approval processes and multiple stakeholders who need to be convinced. For example, it is not uncommon for a $100K deal in this segment to take a year, which is why it is vital to ensure that there is a genuine hair on fire pain and that all the stakeholders involved are aligned on the need to solve it. In this segment it is also worth considering if landing an initial smaller “deer” sized deal e.g. $25K, and expanding to something bigger over time is a faster option (although deer sized deals may still take just as much time as a $100K one in this type of company).

    Segmenting by company size is relative to your product, for example, a 1000 person company for some start-ups will be a “rabbit” whereas for others it will be an “elephant”.

    Regardless, segmenting is important because of the different needs, buying processes and length of time and effort involved, and because a good balance of different company sizes in your sales pipeline gives you the best possible chance of hitting your revenue goals.

    Metrics matter

    As with any type of testing, recording and reviewing your learning and tracking key measures is the key to success.

    The learning from discovery meetings will help you to refine your ICP hypotheses and variables, and key measures such as –

    • How many discovery meetings are being attended by prospective customers
    • The conversion rate of meetings to qualified opportunities
    • The conversion rate of qualified opportunities to closed deals

    Will help you to determine whether it is worth focusing more effort and resources on this part of the market or if it is time to move on and test another.

    The pain is worth it

    The process of finding an ICP market is often frustrating, requiring persistence and intensive effort.

    However, founders that persevere, testing their hypotheses with discovery meetings, tracking their metrics, recording learnings and refining their mix of variables, will eventually be rewarded with a secure beachhead that will put them on the ideal path to sales repeatability and that all important next funding round.

    *Techniques for securing meetings will be covered in the next article in this series.

    **Paraphrased from Geoffrey Moore’s “Crossing the chasm”

  4. Paid’s Journey to Building an Enterprise Sales Motion

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    In this interview, we spoke with Natasha Foster, the co-founder and COO of Paid about the evolution of their go-to-market (GTM) strategy. This Q&A applies to any founders building products for the enterprise and looking to transition away from founder-led sales. 

    Sneak peek – 5 takeaways:

    1. You can’t build a best in class sales journey without a Customer Success team to drive a best in class customer experience. Customers buy from people and want to know they’ll be taken care of
    2. To close enterprise deals, encourage the customer to share their ideas for the future of the product & make them feel part of your product growth journey. Treat them as design partners!
    3. Agree KPIs with the customer before kick starting the pilot! Set timelines, front-load as much of the commercial negotiation and get all decision makers on the mid trial review
    4. Qualification and selling is all about shaping the process around your prospects’ needs, not yours (as tempting as it may be to drive your own agenda)
    5. Ask the hard questions on qualification calls and during the pilot to get to the nitty gritty of the customer’s pain. “What’s your nightmare scenario? What would prevent you from adopting the solution?”


    Who are you and what’s Paid’s mission?

    I’m Natasha, co-founder and COO of Paid. My co-founder and CEO is Tom Howsman and we founded the Company in 2019. We help enterprises procure from small suppliers. Today, the procurement process for large enterprises is lengthy and manual. That’s why it’s frustrating and a real blocker for business. For example, onboarding a new supplier usually takes months! With Paid, it’s done in minutes.  

    Paid injects magic into procurement and turns it into a process that people love. How? It creates certainty and security on the supplier side. On the buyer side, it allows you to gain control of your business and turn procurement into a profit centre. Your team can finally focus on what matters and add value, by negotiating mega discounts rather than dealing with non-strategic suppliers. What we really want is to take procurement out of procurement – to enable permissionless procurement for low risk contracts.


    Where are you in your GTM journey (company size, traction, who’s selling, how you got there so far?)

    Tom and I started as a duo, in the trenches together leading sales to large enterprises from the get-go (2020). We realised that only one of us needed to be accountable. I had no background in sales. But I can speak to our procurement buyers as a peer, having worked in large corporates and seen the supplier onboarding process first hand. I also know what it feels like to be a small supplier, having worked at a small company partnering with large corporations. Naturally, I turned out to be the one driving sales. Founders need to own sales initially to deeply understand the product and pain point.

    Our first commercial hire was a Business Development Manager (‘BDM’). We had no playbook so early in our journey. That’s why first commercial hire was working with me 50% on SDR-style work and 50% on strategic GTM support (driving analytics/research, AB testing our messaging, testing sales tactics). We also brought in an ex consultant early 2021 to help us push the process along. Those initial sales efforts led us to landing 3 very large enterprise clients, including BT and ISS. 

    Onboarding those clients made us realise that we couldn’t build a best in class sales journey without a Customer Success team. We recruited a CS expert to be laser focused on the customer experience and community. 

    Throughout each sales process and onboarding, we learned which stakeholders we should be targeting, how to adapt our communication with them and how we help them achieve their goals. Today, we feel we deeply understand our prospects’ challenges and pain points. At this point, we feel it’s the right time for Tom and I to transition away from founder-led sales. We plan to hand over sales leadership reins to a Head of Sales who will hire SDRs and other sales reps. We’ve actually tried to hire a sales leader early on, but it was just too early for them from a pure sales perspective. They’re usually driven by metrics and comp!


    What’s striking is that your very first customer is one of the largest organisations in telco. Many mature companies simply cannot close such a deal due to its complexity. Can you please share with us how you closed this first customer?

    It took a lot of cooperation, organisation and perseverance on both sides! We had strong champions within the organisation – both at a senior level (we got the most incredible support from the Chief Procurement Officer) and at the operational level (Procurement Manager implementing the software). 

    Although Paid has an easy integration and implies no change in users’ behaviours, decision making on the enterprise side is still highly complex. Plus, you need to find the right balance between pushing proactively to create urgency and exercising patience. Things take time in enterprise sales! You don’t need a sales background to understand that. 

    We spent a lot of time with our first and second enterprise customers to (1) truly understand the pain points they were experiencing (that we could solve!) and to (2) find where the cost associated with the pain points was located. We then tailored our proposal to customers based on what they’d find most attractive, and to match the pricing (and who paid for the product) with the location of the cost drain! 

    Finally, to close the deals, we were very flexible about the ‘art of the possible’. Whilst we were careful to avoid promising bespoke development, we encouraged the client to make ‘suggestions’ for our product roadmap, to get them excited about being part of the product’s developmental journey and to make them feel special in getting a software ‘just for them’ (even if from our side it actually wasn’t bespoke!)

    Also, once the deal is closed, you can’t leave the account to just become successful on its own. It was crucial for us to keep building deep relationships with customers post deal completion. This is why Customer Success is so important in enterprise sales.


    Do you remember the very first step you took as a founder to start taking your product to market?

    We were lucky to be introduced to senior procurement professionals by our investors. We sold the dream of what we could become, leveraging creative language to bring to life how our software would fundamentally change the life of procurement teams. This is despite the fact we didn’t have a product at the time!

    One of our very first initiatives was to build brand awareness by publishing Q&A blog posts. We looked for the most open-minded and innovative people on LinkedIn, deeply focused on transformation and change. We invited them to Q&A sessions. We got a 50% response rate on our cold emails! This validated our thinking around the fact that procurement truly is an under-appreciated function.

    Some of those conversations turned into sales opportunities and awesome sources of information to help us sell better. Ultimately, the Q&A evolved into our podcast “Procurement Trailblazers”. We love shining a spotlight to show the value Procurement teams deliver.


    We can’t really talk about enterprise sales without mentioning pilots. Pilots are an important part of the sales process for Paid. Can you walk us through the pilot process and the key learnings you’ve accumulated to increase conversion rate?

    In the beginning, we had the age-old dilemma about whether we should run free or paid pilots. 

    Our first pilot was free and we literally ‘let it happen’ – no prescribed process and success criteria. We only instigated commercial discussions towards the end of the pilot. We managed to close the deal but it took a lot longer than we wanted. We realised 2 things: 1/ it’s key to define KPIs upfront by flagging what clients are most excited about; 2/ if you structure the pilot well enough, having a free or paid pilot doesn’t matter too much.

    In our second free pilot, we proactively defined KPIs with the client before the pilot even started. The client signed an opt-in contract whereby they had to express consent at the end of the pilot to continue as a customer. This time we front-loaded the commercial discussions, but it still took an additional month to get everything finalised. 

    Lesson learned – we need to be laser focused on conversion half way through the trial (and not wait until the end)!


    How do you think about the role of Customer Success in pilots?

    The Customer Success team should work with the customer on the pilot from day 1. Paid is about adoption – training users to leverage the software even before the trial starts saves time. And the most important thing: you should hone in on what the users personally care about achieving, rather than the value you envision adding. 

    All in all, a successful pilot implies a close collaboration between CS and Sales – the Sales rep should identify the decision makers and how to secure time with them. Plus, don’t underestimate the importance of having all decision makers attend review sessions throughout the pilot, to secure their ultimate approval!

    Today, we moved on to paid pilots whereby we price the trial the same as the subsequent contract to create a smooth transition. We also run mid trial reviews with all decision makers in the room to share the value of our product. It’s a great way to get user feedback and solid quotes from users and suppliers.


    Putting things in perspective, what would you have done differently and why?

    We should have better structured the pilots from day 1, setting up clear objectives and timelines. We realised that the best way to sell is to deeply understand your prospects’ needs and drivers, and constantly show how your software helps them get closer to their goals (and not yours!). We learned it’s very important to understand the structure of the organisation and who’s going to see the value from Paid. Do your best to involve these people in the decision-making process (and the ones paying for the product!)

    Finally – don’t be afraid to ask the hard questions to get to the bottom of their pain points and needs – “What’s your nightmare scenario? What would prevent you from adopting the solution?” This is the only way you get into the nitty gritty of things and position your product efficiently.


    What’s been your biggest challenge and how did you deal with it?

    Our biggest challenge has been twofold:

    1. Reaching the “aha moment” with enterprise prospects: we needed to introduce demos earlier in the sales process to help them understand the value of our solution.
    2. Navigating the lengthy enterprise decision making and implementation process. This is still work in progress! To date we’ve tackled this through aligning our pilot and contract pricing, investing in rapid deployments and setting out a timeline for implementation & success criteria for trials. On this, Crane helped us think about pricing as a lever to accelerate the sales process. Their experience across pricing and GTM strategies got us to AB test approaches to achieve the right structure (for now). They challenged our GTM strategy where needed. Especially around the best way to transition from a trial to a full contract.


    What are the top GTM books that you’d recommend to other founders?

    • The main one is “Influence (the psychology of influence)” by Robert Cialdini, because I love the psychology of persuasion. Great read to understand how people are influenced to do things, all based on statistical surveys.
    • “Never Split the Difference” by Chris Voss. Great advice on structuring pricing and having commercial conversations.
    • “Drive” by Daniel Pink. Ephemeral – very interesting author. 

    All 3 books speak about needing to understand what the person on the other side actually wants (vs. what you think they want).