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How to Do Things That Don't Scale for Sales Obsessed Founders

Written By @RajenSanghvi

· Sales Hacking,Deal Progression,Lead Generation

For most of you early stage founders, you're likely familiar with Paul Graham's famous essay: Do Things That Don't Scale. If you're not, I'd highly recommend taking a few minutes in reading that first. At a tactical level, the essence of this essay encourages startups to really get their hands dirty; to be willing to do the manual, tedious, and perhaps annoying (but necessary) work, to really get things off the ground. The following quote from the essay, is my favourite from a sales standpoint:

A good metaphor would be the cranks that car engines had before they got electric starters. Once the engine was going, it would keep going, but there was a separate and laborious process to get it going.​ - PG

As a founder, you need to be that crank to your startup's sales engine. Or perhaps you're a sales person working at a larger organization; then think of yourself as running the "startup" of your own sales territory. Either way, the only thing that matters is moving the revenue metric forward, and that means doing everything in your power to make it happen. Lately, I've found myself repeating many of my own unscalable sales stories to the companies I work with, and decided to turn it into a post. So with that said, here are a few unscalable sales tactics broken out by each stage of the B2B Sales process.

Lead Generation with Conferences & Trade Shows

Be The Last to Leave - If you're attending a trade show where your prospects are exhibiting, it's tough to find time to talk to them. By being the last person to walk the trade show floor as things are wrapping up, there's a good chance you'll run into them when they have a bit more free time. Use this time to connect with your prospect, maybe grab them a coffee, and set up some time to chat at a later date. 

Do a Little Competitive Reconnaissance - Be the first person in the morning to get on the trade show floor and take a walk. There is a good chance that your competitors that are also exhibiting there, and will have their booths set up with nobody around. If there's free marketing collateral or case study flyers lying around, take one. If they have screens up with customer logos on them, pull out your phone and take a picture. Guess what, now when you prospect that competitive account, you can reference what you know they're already using today to your advantage.

Be a Volunteer - There are so many benefits to being a volunteer at a trade show in the early days. The best volunteer role to hack sales, is running the registration booths early in the morning. In addition to getting a free pass, there's also a good chance you'll get insider access to attendee lists to see who's attending. This can be incredibly useful when you're trying to map out an organization.

Lead Generation with Inside Sales

Make Middle of the Night Mapping Calls - Call the main office of a prospect account in the middle of the night. With nobody around to answer the call, there's a good chance you'll get an automated system that will direct you to the person (or department) whom you want to speak to. This works especially well when the automated system gives you a message like: "Transferring you to Bob Smith, Extension 227". Then take the time to listen to his voicemail and look him up on LinkedIn. Guess what, now you know how to reach Bob directly and likely his title too. Use this tactic to map out and create a little prospecting org structure.

Conduct Prospect Research like a Stalker - Anything that gives you a leg up in a conversation or build rapport with a client is worth the time. This goes beyond the company website, recent news, and the individual's LinkedIn profile. Treat the prospect you're about to get on the phone with, as though you're about to go on a first date with them. That's right...this means Facebook stalking, Googling their name, viewing their recent activity on LinkedIn, reading any articles they were mentioned in, scoping out their Twitter account (and then reading what they're reading), everything. When you feel confident in understanding the company's goals and knowing your prospect, before getting on a call, you can increase the chances of having a meaningful conversation. Read more on meeting prep and building rapport here.

Engage in Hyper Personalized Email Outreach - Instead of trying to come up with the optimal template to generate email responses, go manual. Use some of the research you've done, to draft an incredibly personalized email that increases your chances of a response. As you do more of these, and start seeing more responses, you'll now have some better data around what's working and what's not to create a template that's actually useful.

Follow Up with Hustle - Don't be afraid to keep following up, and don't expect your product to sell itself. Your prospect may say call me back next week, or next month or next year. Keep doing it, keep following up. As an example, I've once followed up over 30 times over the span of 6 months before getting an opportunity to demo to a prospect. While I wasn't spammy in my emails or telephone calls, I did have to find creative reasons to reach out every single time. Sometimes you'll even find prospects that actually appreciate your hustle; they'll chuckle every time you call them, and so long as your polite and trying to create value, eventually they'll feel like you've earned their time and agree to a meeting.

Opportunity Progression

Try to Poke Around A Little On-Site - If you're on-site, intentionally take a bit longer to pack up your laptop. Usually there is someone (typically junior) who's been assigned to walk you out of the office. By taking long to wrap up, the other individuals in the room will leave giving you a bit of 1 on 1 time with that junior individuals. Take advantage of this 1 on 1 time to get their feedback on how the demo went, try and uncover who your decision maker is versus champion versus influencers etc. In addition, if it seems like they have the time, ask them for a short tour of the office. This is an opportunity for you to learn who else does what, perhaps shake a few more hands and get your tentacles deeper into the organization.

Do Some 'Wizard of Oz' Magic in Your Demos - While this will vary depending on the nature of what you're selling, ANYTHING that you can do to create a more customized demonstration of your product is something worth considering. I'm not talking about just swapping out names and logos (as that's kind of table stakes nowadays anyway), but going above and beyond to really wow your prospect. Is it possible for you to get some sample data from your prospect to illustrate the point? Can you scrape the company's website to bring in the images they are using versus stock photos you have internally? Can you create a custom demo environment to illustrate integration between specific tools they are using in house that you work seamlessly with? I know this stuff takes time and I get founders have a lot on their plate, but if you're growth metric isn't increasing at the speed you need/want it to, closing even 1 or 2 deals can help. Give yourself the best chance of doing so.

Try and Manufacture Serendipity - When prospects go silent, it's typically not a good sign. You can either way to get the bad news, or you can try to get ahead of the situation. Knowing your customer well enough to know where they have their morning coffee or typically grab lunch, and then serendipitously "bumping" into them is one way to get back into the game. By the way, this also works over the phone. If you're trying to get a hold of a key decision maker and they've been ducking you, try calling the receptionist and learning what time they get into the office. Then use a blocked number, and try calling them first thing in the morning when you know they get in.


Experiment with Pricing - If you're a pre-product/market fit company, there's a good chance you're still figuring out your licensing model. When qualifying your prospect, don't be afraid to experiment with your pricing model by trying to charge more. It's more important to figure out your true value and get paying customers, than it is to adhere to some arbitrary pricing model that you've put in a slide deck.

Negotiate with "Free Stuff" Instead of Money - Come up with a few additional offerings that you can give away as "free stuff" instead of reducing the pricing of your SaaS subscription. For example, consider waiving a setup fee, or giving away a custom training package as a way of providing additional value to your clients. If you've done a good job of qualifying the opportunity and articulating the value of your product, at this stage, your prospect will care more about getting a good deal rather than getting a specific pricing discount.

Go Face-To-Face When It Matters - Whether you have to make a long drive, or get on a plane, if you're in the critical stages of a deal, really consider going to meet your prospects in person. I totally understand the risk and it's a lot easier to say 'get on a plane' than it is to fork out the cash. However, you can be tactical about this in making the most of your investment. For example, if you're about to spend $1500 on a roundtrip flight and an AirBnB trying to close a deal, pick up the phone and start booking other meetings in the area. Whether that's with other prospects, or influencers you want to meet for a coffee, there are ways to meet people in growing your business in every city. I guarantee that with the right hustle, you'll be able to book up your calendar. 

Quick Note on Customer Success - The post sale Customer Success process, is a whole section I've intentionally left out here. This is largely because much has been written about doing everything you can to provide your clients with a phenomenal experience as a startup. 

Do you have any other tips for doing things that don't scale with respect to sales? Let me know as I'd love to add to this list! Feel free to email me at or leave a comment below. Thanks.

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