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How to Sell – a guide for SaaS startups (entrepidpartners.com)
303 points by jhchen on May 30, 2018 | hide | past | web | favorite | 44 comments



> Common mistakes made by salespeople and founders:

> - Thinking their goal is to close a prospect on the first call

> - Giving a full demo and presenting pricing on the first call

> - Prematurely trying to shorten the sales process

These are mistakes? Having been on the receiving end of many "sales processes" I would say the shorter the sales process, the better. I often feel like companies who are too deep into doing high touch sales don't really respect my time and are shocked when I tell them to cut to the chase and yes, I do expect to hear about pricing on the first call, otherwise there won't be another call.

Disclaimer: I have zero patience for abundant sales processes.


These rules only apply for higher-cost products and / or enterprise clients (in which the latter implies the former, anyway).

Your sales team can only spend as long on the customer as the ROI of having salespeople allows. If you're selling £19.99/pm software to individuals, you probably don't even need a sales team. But if you're selling enterprise software to Fortune 500, you'll need a dedicated salesperson, or account manager, to look after and nurture prospects over months or years.

So yeah, there are products and price points where if you're not closing first call you're probably wasting money.


If you're selling cheap software you don't want a sales team, you want a marketing team.


Main goals of a salesteam include building accurate pipeline, and closing that pipeline as quickly as possible.

In B2B, level of touch definitely depends on the size of the deal. Excellent discovery + qualification done quickly is super important for larger companies.

E.g. signing up for Dropbox for my 2 person company is (and very much should be) self service, with transparency around price and what it will look like as I grow in the short run.

Signing up for Dropbox for an enterprise company for thousands of licenses, each with different apps, permissioning, environments, infrastructure, etc should be a much in depth conversation. Typically enterprise clients with volumes also expect to have discounts due to their scale (they know they're worth $$$), and in order to have a properly managed negotiation, a sales team needs to full understand who they're selling to, what they care about, what levers can be moved, decision maker, timing, etc. All of these attributes are typically much more distributed in large companies vs leaner entities with 1 decision maker.

First call closes are great, what I can say is that I've never heard of a $1mm deal close on just one call.


Yep exactly. And for the enterprise company it's never going to be a single sign off. You'll need to get IT involved, maybe legal, probably finance, maybe procurement. Every company has a different process, and everyone will want at least a few people saying "yes" when the price is high enough. Enterprise sales is more project management and scheduling than it is about learning the magic words that close any prospect.


I agree if what the person is selling is solving a well understood problem. But what if it's something that you hadn't really thought much about before and need to take some time to wrap your head around? In sales, I think it's generally a mistake to talk about pricing until you've established the value of what you're offering first, which is where I think this advice is coming from.


Then I would never sell you a thing. Ever. Anyone that buys on price is a worse customer than a person that buys on education, and churn of bad customers is a silent killer. That doesn't make you a bad person of course, so please take no offense. It just makes you an unideal customer for pretty much everything I've ever sold in 20 years.

High touch sales processes exist to provide certainty when making a big purchasing decision. Prospects often think this is for their benefit, all this interaction and courting. But it's also for the benefit of the company courting you. Making sure there is no charge-back and that the client is set up for success is a big part of being a successful salesperson.


> Prospects often think this is for their benefit, all this interaction and courting.

I am sorry, but I fail to see how taking many hours out of my productivity does benefit me.

Yes, I do want to know if this is the right purchase decision. So I request a trial and a live session with an engineer who can answer my questions as we go over the product in real time. I get to ask questions related to our workflows and discuss solutions and even workarounds.

This helps me build understanding for their product the way my brain works and not the way their demo is designed.

Demos are designed to impress, to highlight the strengths and hide the weaknesses of a product. They do not mention the corner cases, and often are oblivious of our workflow so do not cover our needs.

The process I described is ultra efficient for both parties.

Wooing me, playing games, mentioning my name every 90 seconds, qualifying every question I ask as "great"... all of these quickly and drastically decrease my trust in the company and the product.


I agree completely: all the "tricks" in the world (mentioning the name every 90 seconds, every question is "great") is generally a waste of time. I roll my eyes as much or more than you when I get Sandler-ed or Spun or whatever the newest training advises.

But the process you've described (demo with an engineer) is far from ideal and not always efficient. That process solves the problem you know you have. That's ok, I guess. But "the problem you know you have" is never the full problem...ever. There is always something behind that problem and something behind that one and so on.

A good salesperson may let you see the demo, close the deal and sell you a solution to the problem you have identified yourself. A great salesperson will first get you to invest the time in understanding the entire picture and then sell you the solution for that. Sometimes that is a LOT more expensive and expansive. And sometimes, believe it or not, an honest salesperson will sell you something less than what you originally came for. It's why some people buy $10 web hosting and some people buy $X,000 web infrastructure. Education, process, understanding. Weighing benefits and costs. Understanding risks and assurances.


I understand your point, and you aren't wrong, but you are short-sighted. You may only sell to big clients now, but you are also leaving a lot of money on the table for yourself, not your company, yourself.

You've been selling for 20 years? How many of your customers have you had for longer than 3?

Now I can hear your mind churning, 'but I'm at a different company now! I don't sell the same thing!'. It doesn't matter. Sales is sales. And the best sales people foster relationships for years before they really sell the big bucks. And can go back to those same clients and sell different products and it's easy because those clients know them and trust them.

Ever get that little pang of jealousy wondering why that guy you know in sales plays golf every day with clients and doesn't seem to do much else? It's not because he's just that good. He's not. He might even suck. It's most likely bc he has been building relationships with those clients for years and they would buy a cactus as a new pillow if he asked them to.

This attitude of telling the little guy to piss off bc he isn't your type of client might make for some ok sales now, maybe you even have a shiny BMW, but it doesn't make for long term relationships with people who trust you. Once those people at that big company move on to bigger and better things, you'll be stuck grinding it out with whoever they replace them with.

I take it you work hard. You're certainly passionate. But after 20 years in sales, you shouldn't have to be working hard. Whether you changed companies and products every six months or still work for the same company, you should have been building relationships.

Instead you are content writing off the little guy as a waste of your time. The same senior management you grind it out to sell to now who was a little guy 20 years ago. And the same little guys who will be senior management in 10 - 20 years.

I imagine you'll still be grinding it out every day then also, instead of playing golf like you should be.


I'm not sure your post was meant for me even if you think it was. I dont write off the little guy, I write off the person that just wants to know about price price price.

My churn rate is low precisely because I take time to learn what they want then provide what they need. I work with clients that are a good fit in both directions and got out of the "anything for a buck" game years ago.

I work hard building my businesses, but I don't have to work hard at sales precisely because of what you said - I've built relationships and skills that make it fun for me to sell. I work about 5 hours a day, travel a ton and play lots of golf. ;)


agreed. Whether someone cares only about price, is a separate trait from whether that person is a big/little guy

in the very original comment, it said "I do expect to hear about pricing on the first call, otherwise there won't be another call. Disclaimer: I have zero patience for abundant sales processes."

this person isn't asking about price because he/she is "little" and can't afford it. Even if the person is a big guy with a lot of $, he/she will still haggle you on price, because that's his/her worldview.

besides, it's unclear that a little guy with a "zero-patience policy" that fixates on price price price as a principle, will likely become a big guy some day.

Even if they did become a big guy some day, you would still have a lot of problems making money from them.


I agree with absolutely everything in your (really well written) post when applied to a random salesperson who fits the description - and I'm sure there are many, many, many.

But I don't think goatherders wrote anything to indicate he was in that category. I read his comment as saying he wouldn't sell to anybody who was completely disinterested in a relationship, not that he wouldn't sell to a less senior person.


This sounds really good in theory, but unfortunately it's just not true.

There are sales reps that play golf with clients. They've been selling to CxOs for years at some of the largest companies like IBM, Oracle, and now Google. They have the relationships because they've worked with the CxO before, selling another massive piece of software. It is not because they immediately shared pricing and cow-towed to whatever the prospect said at the very first meeting when the CxO was a Devops eng or a FTE without budget.

The majority of sales is opportunity cost and focusing your resources on the deals that matter. Working hard and fulfilling every wish of every prospect is a waste of time and the easiest way to fail in sales.


As a Solutions Engineer, we always want to conduct a "discovery" session so we can tailor a demo to your context. Otherwise we don't know what is interesting to you and we are effectively throwing darts blindly hoping to hit close to what matters.


Another data point to support your view: I'm the same way. In fact, I want to hear about pricing in the first email you send me before we do a sales call, and maybe a short demo video. If I need help, then we can do a full demo. Otherwise, just take my damn money 'cause I desperately want you to solve my hairy problem.


I went into a furniture shop and the guy was pressuring me to buy the couch almost immediately even after I said that I am just browsing what's available and didn't plan on buying until I move places. It was so damn aggressively annoying that I'd not buy from him on principle alone.

There are definitely good ways to go about the sale process and shortening the timeframe when it suits the customer is absolutely fine. when they don't respect that it's not. It's all about the customer and doing the right thing for them... if that means that you suggest someone else's product or service then so be it(and is actually a good way to get referrals and trust from the customer who still might buy from you).


> I have zero patience for abundant sales processes

What? You forego the steak dinners and golf outings?


When you do that, you’re sending a buy signal. If they’re a good salesperson, they will find out if you are a decision maker.

The high touch salespeople have a few hard jobs — match client to solution and figure out WTF makes a decision.

A lot of times, the big mouth in the room is just loud. They need to balance keeping you happy with selling a far more lucrative solution/vision to the guy with the money.

I usually play the direct guy role in these sorts of negotiations, and we do it because once you anchor to a price ($n-x%), you need to fight for every marginal dollar. When you start with the big bundle with the business vision guy, you start at $5*n and negotiate it down by 60%.


>When you do that, you’re sending a buy signal

I don't agree with that. I also don't have any patience for tedious sales processes. If I'm talking to vendors, it's because I at least want to buy something, and I always talk to a few of them. My goal in talking to them is only to get the information I need to make a decision. Being expected to sit through a sales script before my questions are answered is very frustrating, and usually sends me a "our product doesn't actually do what you want" signal.


SaaS founder here. I share your preferences when I'm on the receiving end, but some of our customers have taken months to bring onboard, including a couple of our lighthouse customers. It's my decision to accommodate onboarding cadence from minutes to months, primarily because this fits our GTM strategy. You're being alienated by process, and it's not impossible that in some cases that's a deliberate choice to segment a market by customer culture.


As a consumer, completely agree.

As a buyer in a B2B context, completely disagree.


I found this ~20 page guide Fog Creek put out a few years ago and it got me excited about switching from a technical role into sales. I'd recommend it to anyone who wants a high level understanding of Enterprise sales.

https://www.fogcreek.com/guide/The-most-basic-things-your-co...



i've worked with Tyler and Entrepid across multiple of our portfolio companies at Axiom Zen and been super impressed every time

ZenHub wouldnt be where it is today without Tyler (we have dozens of Fortune 500 companies as customers)

Tyler is a close friend so at this point i am biased, but Entrepid has built a team of humble, holistic thinkers with deep expertise in sales and high-touch growth strategy


Nice guide for high-touch sales.

I'd love to see something similar for low-touch/no-touch sales SaaS.


"Low touch / no touch" sales is also known as "marketing." I don't know you or your intentions so this may not be directed at you, but I've found that most people looking to develop a low-touch sales engine are really saying "Ew...sales...I don't want to have to do that. Maybe if I blog enough and my site looks good I won't have to actually, you know, TALK to potential customers."

I also find that anything above about $70/month MRR is going to require talking to the person. $70 is a limit that most companies will allow to be expensed without much question. MAYBE you can get that number to $100 in the right market. Above $100? Good luck. And if you are selling a $100+ product with no-touch then you are really missing out on TONS of business that could come your way if you just put in some actual sales effort.


If I could offer some perspective from someone in the sales trenches:

Cold calling does not work. No matter how good your script is, your email, your personality, your talk track, your data sources, your persistence, cold calling does not work. It is a poor ROI.

All real sales are made either through the customer opting in to communicate (response to an email blast, inbound lead from the company phone, a referral etc)... or through nepotism and cronyism and ivy league networks of multi millionaires. Hint: this is how Oracle is alive to this day.

If I was in charge of selling a product over $100, I would create the most awesome, viral content you would ever see about our product. I would release a free version to 99% of the world that is truly usable and awesome.

This is what join.me did to compete with Webex and Skype for Business and GoToMeeting.

Remember: if you don't have an existing network, you don't have any business.

Start marketing before you start selling.


Bryan from Entrepid Partners here... we find that highly targetted, outbound cold emails are actually the best place to start prospecting.

In our experience, if you do the extra work to personalize the email and focus in on why your product/service is relevant to the buyer's pain points, we've seen response rates as high as 30% with the majority of those replies turning into an intro call with the buyer.


Hi Bryan :)

>highly targeted, outbound cold emails...

...are neither scalable nor calls, in my mind. Here's my opinions:

1) I am currently manually building my own unsolicited email list for the purpose of marketing my b2b service. I have good, quality data sources with no bounce rates and right personas, but it is neither cheap nor simple to enter this data manually

2) even if I send these people highly targeted and well-crafted emails that are friendly and insightful and pithy, it is a slow process with diminishing returns...

3)... because most people add me to their spam filter these days. It is trivial to do so.

I would infinitely prefer to invest my time in creating excellent, viral content and offering users a free entry level service with few restrictions.

I would then spend all my time obsessively devoting myself to those users who have a big budget and greatly desire to receive communication from me.

Lastly, I dare say that someone who responds to a cold email will probably just end up kicking tires.

Tire kicking is automated away with my free demo.


Certainly more than one way to do this, but I agree with Bryan.

Highly targeted email lists are scaleable enough and there is plenty of tech to make them more personal than ever. I disagree a great deal with the idea that cold respondents "end up kicking tires." 100% of my marketing is cold email. 100% of the marketing I do for clients is cold email. I'm happy with my ROI and so are they.


I do Chef and Ansible development. I'd love to know how to sell and find more good customers. I have a long-term customer who's had me on what amounts to a staff augmentation project for 3 years. I know it won't last forever. How would you go about finding more projects like this?


Email me and I would be glad to have a back and forth for free. Good sales process comes down to patience and persistence and I can coach you through both if you dont mind the sometimes-slowness of email.


Kudos to you guys. Please report back in a few weeks with the metrics on the number of leads this created for you. I'm in the same space and this content marketing is golden.


This actually scares me.

I want to bootstrap an SaaS company focused on enterprise / b2b soon and being bootstraped I can't afford to hire an sales rep/ account manager (or be one myself while working on the product) for what looks like a long process.

This is definitely a scary thought in my opinion.

Fingers crossed, I hope that's a good problem to have.


We are exactly at this stage right now. Bootstrapped, enterprise SaaS, ready for initial sales. This post could not have been more timely for me.

I'm not sure if this is possible in your niche, but we are partnering with a consulting company which provides services in the same industry/niche. We will give them a cut from the sales to do this exact process. Many leads will come from them as well. I could not imagine doing this any other way at the moment. Eventually we will certainly hire a full time salesperson.

edit: we got really lucky that this consulting company had some biz dev people who used to do SaaS sales at a previous employer.


You have to make time for sales. You HAVE to. To say there is no time because you are busy developing is dangerous. Even one hour per week can be meaningful. But you have to do it. No one knows your product, service or vision the way you do.

One of my companies builds the sales funnel for SAAS and digital agencies. We handle the entire top of the funnel (lead gen and nurturing) so by the time it's a qualified opp it's actually a prospect that has an identified pain, time line and budget to go with an understanding of our clients solution to their problem. But we dont ever close the business precisely because in digital and SAAS the results are so much better from the heartbeat then the hired gun.


In our experience, the founder should close the first 3-10 enterprise deals on their own. When you chose to outsource, you may close some deals, but you lose out on the early customer product feedback.

The relationships with your early customers are key. You need to make your early customers your biggest fans to show how your product changed their business through references and/or mini-case studies.


Oh, I am definitely in on all calls at this point. And thanks for the rest of the advice, I am trying to follow it already.


As Joel Sposky said, even the best, most necessary product doesn't sell itself magically. Setting up a website, selling on Amazon basically won't make you close a single sale.

You must devote a day or two a week to sales and marketing, making noise on LinkedIn and a blog, and awesome videos, then connect to people and propose them a demo of your service. That's crucial to market fit, you must have at least some prospective customers to be sure your products solves an actual pain for them.


Is there an awesome list for business that this can be added to?

--edit nevermind, here it is:

https://github.com/cameronroe/awesome-marketing

it's not added to the main awesome list, so I'm making a pull req for that too.


Excellent guide - rings true.


This is super helpful!


I'd recommend also reading this: https://medium.com/@fairpixelsco/b2b-growth-strategies-by-in...

It's an analysis of successful growth strategies used by B2B SaaS Startups that are listed on Indiehackers.com

As well as the Saastr podcast. Full of gems on how to sell.




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