How To Sell
Sales at a startup is counter-intuitive.
This post contains everything I wish I’d known, before I started, about doing sales at a startup. It’s really hard to find good information about sales without a lot of fluff, so I set out to write down as much as I could about it.
The biggest mental shift I had to make to sell successfully was to realize that:
Your job is not to “sell”, your job is *qualification*.
The actual “selling” process goes extremely smoothly if you’ve qualified the person correctly. Most pain is caused by people not doing this qualification process correctly, overselling or underselling their product, and then being mystified by the inevitable “no” / being ghosted by their customer.
Once you’ve qualified somebody as a good fit for you, actually selling to them is remarkably easy and seems to “just happen” effortlessly. This is one of the most surprising things about sales.
Qualification means asking the correct set of questions to determine if the prospect is a good fit for your product or not. Once your startup has product-market fit, you will have a good sense of what these “qualification questions” are. In our case at GoCardless [1] (where I learned how to do this), these were questions such as: “how many payments do you take every month?”, “how do your customers pay you at the moment”, “where are your customers physically based”; these quickly enabled us to figure out how big the customer/prospect was & whether they were the right fit for the specific payments solution we had.
The #1 rule of doing a sales call is: be quiet.
Most people talk way too much in sales calls. You should aim to be talking for about 20% of the time, with your customer talking about 80%. If you didn’t get this ratio, it wasn’t a good sales call. Sales is fundamentally about listening, not about talking.
Why is this true? Sales is a process of matching: somebody with a certain pain point or need finds a product that meets this need for the right price, and goes away happy. To figure out if somebody has this pain point and needs your product, you need them to tell you about their business and how they currently solve this problem.
Since people do not typically have a well-formed list of things they want out of a product in their head — often they’re just curious / have a vague sense that something is wrong and have just heard of your product from press or whatever — you need to elicit information from them so that you can help them figure out if your product is the right fit. Hence: they need to do most of the talking.
Every sales call needs a structure.
Not only should you have a structure laid out in front of you on a notepad/paper, but you need to lay this structure out verbally from the outset.
The structure we used was:
Introductions
Current process
Pain points & Ideal solution / requirements
Your solution
Next steps & timeline
We made sales reps print out worksheets with these sections on them along with key elicitation questions / soundbites, and they had to physically fill out these worksheets for their first hundred or so sales calls. If you miss out any of these sections, it’s typically a bad sales call.
As an aside, the most helpful book I read on sales was “SPIN Selling”. I didn’t use the specific framework in the book, but it has a lot of valuable stuff around the mental shift you need to make to do sales correctly.
0) Pre-call research
10-15 minutes of prep makes a world of difference. LinkedIn is still the main method here: search the person, find their title, Google them, Google their boss, try and construct a clear picture of the org chart. For example, if their title is “Head of Payments” figure out if there is a “VP” level in the org (typically more senior) — you could try searching {company name} + “payments” as an example and get everyone with the word “payments” in the title.
You want to have a clear picture of how senior the person is i.e. whether or not they have buying power and who they would need to convince to get the deal done; more on this later.
The smaller the business, the more important it is to be talking to the Founder/CEO; the larger the business, the more you want to be talking to whoever specializes / is in charge of the function you are targeting.
Now, onto the call itself:
1) Introductions
Very important and often not done correctly.
First, always ask if it’s still a good time to chat — “we have 30 minutes scheduled to chat, is now still a good time to chat?”. Yes, the meeting was scheduled so it probably is, but there is a nice element of asking permission here and getting someone’s consent here and getting them settled into the call. It also shows respect for their time.
Second, once they’ve said yes, you want to:
Briefly introduce yourself and your title/role at the company
Set out exactly the things you want to talk about. Something like: “So I was hoping to run through: your current process for XYZ, any pain points or issues you have with it, your ideal solution or requirements for a new thing, and then run through next steps if that makes sense. Is there anything else that’d be useful for you to run through?”
Ask if they have anything else they want to add.
This, again, has the benefit of consent: nothing is going to be a surprise; you have freedom now to ask exactly the questions that you want to ask under those categories, and if they want the call to go a different way, they can just say so.
More importantly, laying out the call like this signals that you’re a competent and respectable counterparty who knows what they’re doing. This “signalling effect” is super important: orgs are much more likely to buy from you if they actually think the salesperson was smart and competent, so signalling that you are increases your likelihood of success.
2) Current process
This is by far the most important part of the call. If you do this part correctly, then you know exactly what they do at the moment, whether they are a good fit, and whether they’re likely to convert. In sales this part is most of “qualification”: understanding if somebody is a good fit for your product or not. (If you don’t have this figured this out yet, then you are probably not ready to scale up a sales process).
The key rule for this process is to ask questions that aren’t “yes/no”, i.e. get people to describe what they do right now, expansively.
So if you’re working for Zoom, you want to ask something like “how do you currently do videoconferencing?” Or “how would somebody at your company currently take a video call?” You would then get them to expand on their answer using prompts like “can you tell me a bit more about that?”
Get them in the mindset of telling you the story. Once they finish one part of the answer, you can cue them by saying “OK, so sounds they do X first, what happens then?”
The success criterion for this phase is: by the end of it, you should be able to “play the movie” in your head of exactly how the relevant process you’re targeting looks.
If you’re selling Zoom, you know exactly how they take remote calls. If you’re selling Box, you know exactly how they share files with each other. If you’re a payments provider, you know exactly what their payment flow looks like and you can draw it.
At this point, if somebody clearly isn’t a good fit for your product, tell them so, and refer them to the best companies (sometimes your competitors!) that would be a good fit!
This counter-intuitive point is one of the best things I learned about doing sales. It has a host of benefits: honesty; people are often pleasantly surprised; it builds so much good will that you often get referrals out of it; and it saves everybody time. A lot of sales heartache comes from ignoring this rule and trying to “convert the sale” anyway when it’s clearly a bad idea for everybody involved.
For example, at GoCardless there was a time when we didn’t support customers who used paper instructions, so if a business wanted to take payments from customers where >10% of payments by volume were paper-based, they weren’t a good fit for us. In those cases I’d simply cut the call short and say something like: “A couple things to note: it sounds like you need paper payments support, and we actually don’t support that, so we’re probably not the best fit for you here. If you want recommendations for who else to talk to about that, we recommend chatting to {competitors} as they’re very good.”
One last thing: if you’ve done this part right, you should have some hypotheses for what they’re looking for / what’s bothering them about their current solution. That will come in handy for the next part...
3) Pain points & ideal solution/requirements
Once you’ve figured out their current process, you need to understand what’s broken about it. Note that these can be two discrete sections, but I found they typically blended into the same thing. The key questions for this section are:
What’s the biggest thing you want to fix about your [videoconferencing, payments] at the moment? (-> Why that thing? etc.)
So obviously you’re on the phone with me, and we’re talking about [payments, videoconferencing] How come you chose to take this call today?
What are you looking for? If you could wave a magic wand and have the perfect solution here, what are the top 3 things that come to mind?
What’s important to you here? (If they’re blanking, you can feel free to suggest, but *only if they’re really blanking*. You can say something like “E.g. speed? Support for European countries? Mobile/iPad support? API integration?”)
(Note that these are in my voice; you should adapt them to your voice rather than say them verbatim.)
If none of these are working, you can try and get more specific by referencing their current process — “so you mentioned that people typically do this to start with. Is that a pain point for you?” I usually don’t find this works so well — you’re fishing at this point — but it is worth doing just in case it elicits additional information.
This phase has been successful when you have clear conviction in the 1-3 things they care about most. This has the additional benefit of better qualification: if those 1-3 things are the things you are best known for, great! If not, they may not be a great fit. For example, customers who really cared about a clean/easy API integration were a perfect fit for GoCardless since that was our main advantage early on — a nice REST API. Conversely, if what they really care about is “high touch support” or something like that, then they might not be right for you. Etc.
4) Your solution
You’ll note that at no point thus far have you done a “sales pitch”. Well, if you are ever going to do one then now is the perfect time to do it. That said, “sales pitch” is the wrong way to think of it.
At this point in a call, the person either clearly IS or clearly ISN’T the right fit for you. Moreover, they’ve given you a bunch of information if you’ve done their job right, so typically they’ll be expecting more information from you by this point, so you have “permission” to talk (in any conversation, people get uncomfortable if the ratio is too out of whack, i.e if either person is talking too much).
I hate aggressive pitches so at this point I’ll usually lead into it with something soft like “Great! That gives me everything I need, and [sounding pleasantly surprised here] I actually think we’re a great fit for you based on what you’ve said. Do you have any questions about us / have you had a chance to read up, or do you want a quick 1 minute intro and go from there?”
The “quick 1 minute intro” avoids the dread from their end of some salesperson droning on forever about their thing. This also helps because some people have in fact done research and just want to know a few specific things, whereas others are just curious and need more education.
If they want my blurb at this point, I just tell them what the company does, and then the “pitch” part is easy: confirm the 1-3 things they care about back to them, and then explain how your thing meets those needs, with credible proof points.
“So if I heard correctly, it sounds like you care about a quick/easy technical integration, payments resolving within a day, and France support — is that right?” → give them a chance to confirm
Then go through each trait…
“You mentioned that you care about XYZ. That’s actually a big strength of ours, [clear proof point].” For example — “you mentioned that you care about easy technical integration because you don’t have a ton of developers. Since we’re a tech company, we actually have a really easy REST API that usually takes people less than 2 hours to integrate. I’ll send you the link to the docs after this call so you can take a look.”
5) Next steps and timeline
Don’t forget this part.
The main thing here is you want to leave the call with definite next steps to the extent that you can. E.g. if they need to talk to some other people (typically true) then you want to know exactly who those people are and roughly when they’ll talk to them. You then want to get verbal consent for a follow up call in whatever timeframe makes sense — something like “would a follow-up chat next Monday work for you?”
This is all very contextual at this point and depends on how they’re responding, some people are more non-committal at this stage and then you don’t want to be too pushy about scheduling a call but you do want to be pushy about what information they need to make a decision and how exactly they’re going to proceed here. If they’re not telling you those things, they’re extremely unlikely to end up buying and mostly just want to politely save face / soft decline. (Note that this lesson extends well beyond just sales).
Conversely, if you’ve done your job right and they’re a good prospect then they’ll typically like and trust you by this point and want to get the deal done, so they become your ally and give you the information on what they’re doing next, how long things take, etc. Best case they really give you the inside info on who exactly needs convincing, how to convince that person, how to get on their calendar, etc and will make intros / set up follow up meetings for you. The latter piece obviously becomes more important in larger enterprise sales (a separate topic).
6) Follow-up
Always follow up same-day. No excuses. Do not leave your follow-ups till tomorrow. Just get it done then and there, it shows you’re on top of things and the signalling value is super important, plus lags are the death of sales so you always want to take care of your end of things as quickly as is humanly possible.
Your follow-up should be short, gracious, and include a clear call to action for the agreed next step. For example, if you decided a follow-up call made sense, you want something along the lines of “You mentioned a call next Monday afternoon would be good; I’ll send an invite for 3.30 and just let me know if you’d prefer a different time.”
Finally — follow up relentlessly. People drop off the radar even when the sales call went incredibly well, and it’s usually just because they’re busy, not because they hate you. I can’t tell you how many big deals I closed where I had to follow up >15 times to get the deal done. Be shameless here — you want to get a clear “no” or a clear “yes” or a clear “I’m doing XYZ and it will take me 5 days, follow up next week”. I usually followed up every 3 days or so, but people differ and the specifics matter here.
Thanks to Sarah Constantin, Alexey Guzey, and Nikhil Krishnan for reading drafts of this.
Footnotes
[1] About me: I was first BD/salesperson at GoCardless, a YC 2011 company that’s now a large payments company backed by GV, Accel and so on. I set up and ran the sales, BD and marketing teams and closed deals with many companies you’ve heard of (Box, the UK government, The Guardian, TripAdvisor, SurveyMonkey, etc.) as well as thousands of small/mid-size businesses. I’ve taken many hundreds of sales calls & trained sales reps.
However, I am more of a generalist and do not consider myself a sales “expert”; treat this as “the core basics to get you from technical/non-technical founder to decently good at sales”.