Should You Sell To Enterprise Customers?

Money. The more the better, right?

Customers. The bigger the better… right?

When you’re a bootstrapped start-up, you quickly realize that neither of those assumptions are correct. Of course you want more income. You’re trying to keep the lights on, after all. And of course you want customers who are going to be stable, loyal and paying enough to be worth your investment of time and resources.

But an interesting conversation begins here, as the dilemma of whether or not to sell to enterprise customers arises. Could a high-paying, prominent customer’s demands lead you make decisions you’d have otherwise avoided in order keep them happy? Maybe.

Should you have a hard and fast rule that you avoid enterprise customers? Some would say so, but I’d argue absolutely not. These customers can be good for your business, in moderation. It’s all in how you handle your sales process and your client relationships. It’s in how you decide to serve the enterprise customer, and who at the enterprise you serve.

The Argument Against the Enterprise Customer

Jason Fried made a great case for why a handful of high-paying customers can spell disaster on a small company in its early days. From “Don’t let anyone overpay you:”

We’d much rather have hundreds of thousands of companies paying us a small monthly payment than a few huge accounts covering that same amount. A diverse customer base helps insulate you; a few large accounts can leave you vulnerable to their whims.

He’s right on a number of points. True enterprise sales can be highly distracting to a team that is still trying to define its own products and place in the market.

It’s no small feat to land and keep that enterprise customer.

  • The networking alone can require fancy suits, steak dinners, travel and extensive negotiations.
  • Once the paperwork is signed, extensive software customizations, custom implementations, custom training, solution architecture and more may be required – all taking time and resources from the development you intended to focus on for your larger customer base.
  • Large companies—brand names you want to say you work with in your marketing and sales initiatives—can be tempting to bend over backwards for to keep happy, leading to extra client relations time spent managing the account.

And once you’ve spent all that time on the one or two big enterprise names you land, you risk finding yourself in the position of having these two companies dominate the majority of your revenue. What if one client decided to walk?

It’d be a bad day. Probably a horrible one that taxes your small group of employees tremendously.

And that’s why certain protections have to be made when you engage with such a powerful client.

Don’t Abandon the Enterprise

As a small bootstrapped company, you can sell to enterprises without these negatives, if you structure your mindset and your offering correctly.

Selling only to customers paying you $25, $50 or $75 per month can be extremely hard, especially as you’re building your business. You need an incredible volume of customers to be sustainable at those rates. Meanwhile, having a few higher revenue customers can give you more flexibility in these early growth stages.

So, how do you embrace the enterprise? Selectively! Find a few special cases that not only provide you with profit, but that also allow you to scale for them with limited hurdles and customizations. Find the enterprise cases whose needs and intentions best match where you’re already headed. By doing so, you can sell very profitable, large contracts without most of the extra work and expense required with typical enterprise customers.

You can work with the big customer, without losing sight of the big picture.

Truthfully, your enterprise work is best done if you start… small.

Define Your Target Enterprise Customer

“We want the enterprise customer.”

Correction. We want the customer at the enterprise.

When we say enterprise, we’re not talking about solutions that’ll cover the entire Fortune 500 company. Only in the rarest of cases will you be able to make those sales (and if you do, enjoy spending all of your attention on Company X’s Version Of Your Product, instead of developing Your Product).

We’re too small to manage the processes required to sell and manage the bit of software used by every employee in a 40,000-person company. In our earliest stages, with our 2, 4 or 8 employees, most of us are too small to provide such a substantial bit of software that’s at the core of that company’s functions, on top of all of our other customers’ needs.

But we can get our fill of the enterprise, by nibbling at the edges.


At HelpSpot, we look at departments, groups or slices of functionality at large companies, and identify which sectors we can immediately impact.

We ask: What tasks can we assist with through smarter software solutions? How can we partner with them to make key processes within their part of the enterprise more efficient?

We then connect with a key decision maker within that space of the enterprise, and introduce our solution to them.

It’s not always an easy sell. That enterprise employee may not have immediate clearance to purchase your services, but you will have a much easier time implementing your service for 10 people, or even 40 people, than the 40,000 company-wide.

And that’s okay, because providing your service to 10 People Who Work At An Enterprise does not have to be dramatically different than providing your service to 10 People Working At Your Small Business Customer.”

Make Your Mark On The Enterprise

At HelpSpot, we’ve provided tickets management for individual retail location managers across a 500+ location customer, one by one. We’ve also worked with IT groups within enterprises, and directly supported internal maintenance groups. We’ve provided ecommerce support for a large record label where e-commerce was an important yet secondary revenue stream.

We work with groups within enterprise companies, without incurring the massive headaches and demands that come with the typical enterprise contracts. We provide value to them, while they also provide tremendous benefits to us.

By dipping our toes in the enterprise water, we learn quite a bit about our processes and our products. We learn whether we can sink or swim serving the big brands. We get stronger. We begin building better products, buoyed by the financial support of customers who can afford our top offerings. All the while, they offer us a bit of a flotation device to get us through our worst growing pains.

Enterprise customers don’t have to be the heroes or the enemies of bootstrapped companies. They can simply be customers that help drive your business forward, right along with all of the other companies you strive to work with day after day.

Q&A: What is the best free & open-source customer ticketing software? (“Zendesk clone”)

Disclosure, I’m founder of HelpSpot a help desk app!

I’ve had a bit of a hobby keeping up with open source help desk software apps since I started HelpSpot in 2005. I keep a list of them at Open Source Help Desk List (started that in 2006!).

Now, you’re not going to find any open source help desk systems that are anywhere close to Zendesk in terms of capability. That said, there are a few that are OK. Some of the better ones have become quasi commercial focusing on support and services around their open source apps. Very few of the “pure” open source options with no commercial support are going to be sufficient for all but the most basic of needs.

In no particular order here’s some that aren’t horrible 🙂

  • RT as you mentioned in your description has been around a very long time
  • OTRS – You almost can’t even find their free version on the site but it is there.
  • Helpy – This is a much newer one that’s Rails and has a more modern UI.
  • OS Ticket – Another quasi-commercial old time solution but it is actively maintained which is all you can really ask for in the wasteland of modern open source help desk software.

Honorable Mentions

These aren’t open source but they are free which unfortunately people often use interchangeably.

  • Spiceworks – Ad supported and does a bunch of other stuff besides help desk.
  • Bug trackers: Mantis, Bugzilla – A bug tracker has about 80% of the things a help desk needs (hence why many commercial bug trackers position themselves as help desks also). Many organizations can get buy using a bug tracker as a help desk if they must.

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Q&A: What type of software engineers are high in demand?

Cameron Moll recently had an article suggesting that tech hiring is down about 40%. We run a job board for primarily Laravel PHP Developers and we haven’t seen that same drop off, however, we’re in a more niche group that’s growing fast.

Still, regardless of the specifics I think that software engineering is still a great field with strong growth. I wouldn’t be worried so much about any specific area, it’s really more a choice of what’s right for you.

If you’re into getting a high level of education before starting (or re-starting) your career then Data Science or Machine Learning are probably great areas. As would be Logistics specializations or anything with a focus on serious math + programming really.

If you need a job now or are more interested in entrepreneurial endeavors a Full Stack focus (frontend + backend + some devops) is something we’ve seen a big surge for on LaraJobs. If you have some demonstrated ability in this area you won’t have any trouble finding work. Practically every business in the world now needs at least a few of these, plus you have startups, consultancies, and established software companies all heavily hiring these folks.

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Q&A: What are some tips for a new Tech Support Representative?

Much of what you have to know in a tech support job is dependent on what you’re supporting. There will be seemingly infinite details to learn about the products and/or systems you support.

That said, there’s a few elements that tend to cut across nearly everyone working in tech support. We actually built a help desk training course around them, but I’m happy to share the core elements here.

1) Focus on creating an easy experience for the customers you support. Especially when you’re just getting started, it’ll be hard to learn every system and know every detail. Focusing on doing tasks that help make the customers life easier is a great way to start. Something you can focus on which is often not tied to specific knowledge but rather in putting in extra effort, keeping in constant communication with the customer, and so on.

2) Really get to know your product. It’s kinda obvious, but you need to put in the time to get to understand it at a deep level. Here’s a few tips on that.

  1. Read the documentation (really!)
  2. Check out old support requests – There’s a treasure trove in there. Read through them as you can.
  3. Read “canned” responses – Other staff have taken the time to craft these replies. Reading through them lets you learn about the product as well as be aware of what replies exist for your own use.
  4. Browse your company’s blog – Especially if it’s an active blog. Even if it’s “just” marketing you can learn a lot there.

3) Brush up on email etiquette. – We go deeper on this in the course but a few things to watch out for:

  1. Pay attention to tone. It’s easy to end up sounding robotic in support emails.
  2. Apologize! Flat out saying your sorry about a messup is often highly disarming to customers (in a good way). Just when they’re ready to lay into you, your coming out and saying yeah we screwed up we’re really sorry humanizes you. It cuts through in a way trying to sidestep never does.
  3. Ask for clarification instead of assuming. Yes, this may cause you a few more back and forth emails, but if you’re unsure about anything on the customers end (a system configuration, what version of a product they’re using, etc) get clarification
  4. Read your email out loud. You’ll be surprised at how well this roots out unnaturally sounding phrases.

4) Keep your cool when things go wrong. Everything is going to go wrong! It happens. A lot.

  1. Don’t take a customer’s bad behavior personally.
  2. The customer is not your enemy. The enemy is the problem.
  3. Your job is to solve the problem.
  4. Make time to “move on”. After a rough case, take a walk. Grab a coffee. Chill out for a few before jumping back in if at all possible.

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Q&A: How does one go about raising seed investment for a tech startup?

If you have enough capital to launch you have all the capital you need for now. Get out in the marketplace and see if people actually want to buy what you’re selling. Is your marketing angle right? What features is the product missing? What are customers telling you sucks?

Get that stuff figured out.

Once that’s done, you can take a breath and see if raising capital is even important anymore. Are you break even or profitable? Great! Then you just got the best seed round ever from your customers.

Not profitable or are but see a HUGE OMG opportunity that truly requires large sums of cash today to beat competitors to the space. I’m going to say this is actually extremely unlikely. But, if you’re the special flower where it is the case then go ahead and start talking to angels or VCs at that point.

If you’ve got sales and a vision that’s OMG HUGE raising money won’t be a problem.

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Q&A: Entrepreneurs and Salespeople: What is missing from your current CRM? What would you change about it?

CRMs are a bit of a relic from a bygone era. In the “old days” you had a few channels for leads. The CRM simply had to be a place to track those leads.

Today, on the internet alone you have dozens, hundreds, maybe thousands of inbound lead sources. You also have all the traditional locations as well potentially (cold calls, etc).

Worse, you’d like to be able to track people through the complete funnel. Tracking is hard in B2B because the person who finds you may not be the ultimate buyer.

Worse still, the CRM isn’t the only software involved as it was back then. Now you’ll want that data into mailing list managers, help desk tools, report systems, the bug tracker, everywhere.

It’s a total freaking mess.

Huge CRM tools simply try to do everything and you get a complex nightmare. Lightweight tools don’t do nearly enough.

Personally, I think there probably needs to be a paradigm shift in the overall thinking on what needs to be tracked and how. Not a better mouse trap, but a new way to get mice to where you want them to be.


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Q&A: What was the mistake that killed your last B2B sales deal?

Some mistakes I’ve made in which have lost us B2B sales over the years:

  1. Lack of follow up. Make sure you have a process in place to follow up on every deal. It’s really easy in a small company to lose track of these deals, but it’s even easier for big enterprise buyers to lose track of you! Especially early in the process.
  2. Not understanding that you’re selling a solution. You think you’re selling software, but they’re not buying software at the enterprise level. They’re buying a solution. This is REALLY hard if you’re a small co. who won’t be sending consultants on-site to help them implement, etc. But some things you can do which helpful:
    1. Offer product training via webinar on a regular basis
    2. Offer bespoke customer on-boarding (for an extra fee)
    3. Try and convey the ongoing relationship you’ll have with the customer, product roadmap, touch points with support, etc.
  3. Not building trust. It’s often said that enterprise customers are not paying with their own money. That’s true and it’s great, but that doesn’t mean nothing is being spent.

    In fact, what the internal buyer is doing is often more stressful for them than a founder buying a software product. The founder buys and if it doesn’t work they move on. The internal buyer buys and if it’s a disaster they lose their job.

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