Tag Archive: founder

  1. 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

  2. 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).