Chamber 🏰 of Tech Secrets #7

The secret of selling your product to enterprises

The Chamber of Tech Sales Secrets is open. This week we hit a different class of topic: enterprise sales. My hope is to share some perspective with salespeople about what it feels like to be on the enterprise side and to remind people on the enterprise side about what it feels like to be selling.

I’d like to give a special shoutout to my friend Spencer Huang for reading an early draft of this post and giving me some fantastic feedback about what it’s like to be on the sales side of the equation. This post would be less useful and less empathetic without additions inspired by his comments. 🙏

How it feels to be a target 🎯

I have never had an enterprise sales role, so what business do I have writing about this topic? Well, I am a popular “target” for enterprise sales. In a random week I generally see 15-30 sales emails and 5-10 LinkedIn connections / messages that are sales-driven per day. My all time favorites are the ones selling to Architects… that build houses. 🤣

How does it feel to be on the receiving end? What works? What doesn’t? What advice do I have for those who want their product to flourish because they are passionate about their vision? Let’s dig in.

What to Know About Enterprises

First, some things to remember about enterprises [the buyers]:

• We are people: Big companies are still composed of normal people. It’s obvious but easy to forget. We get busy. We get stressed. We have limited time to accomplish things.

• We often plan really far in advance: In my company, we already finished our essential budget planning for 2024. Yes. In April. Long sales cycles are just part of the game. If we come up with a great idea later this year, we might be able to find money to act. Or we might be ready to spend in 2025.

• Legal takes time too: You already knew this, but in big companies the legal process can be tedious because there is a big brand to protect. Protecting that brand is truly also protecting a bunch of people. See point #1.

• Delete, delete, delete: Based on chats with friends in similar (or higher-level) roles to mine (internally and in other companies), it’s important to accept that most sales emails are going to get deleted without being read, especially if it’s immediately clear they are not relevant to the person’s job. Everyone is busy and there isn’t time to read and reply to everything. If I replied to every message, that would be my full-time job. Literally.

• We can be overwhelmed with volume: Calendars are busy, we get lots of internal and external emails, LinkedIn messages, etc. Be aware that we have lots of things on our minds and aren’t just thinking about your product. If you are overly persistent, you could create a negative brand image by being a tiny addition to a big pile of stress. The straw that breaks the camel’s back. 🐪 I am a low stress person and I can get a little stressed when my inbox is loaded with stuff and I want to be able to kindly dismiss a lot of things, but just don’t have time.

• We like POCs / we are slow at POCs: we like trying things out and seeing how the product really works. We don’t expect to get your product for free. [In sharing this with a friend in enterprise sales, it sounds like they have a lot of bad experiences with long, long-term POCs and our way of working at Chick-fil-A may not match every other company]. Sometimes it takes us a while to actually do a POC successfully because of focus and dependency issues. We may plan to focus but have something that pulls us away. We may not have the data we ended up needing to explore the product. I respect driving a sense of urgency for us to make a decision and to ensure we don’t waste your time. Your time and product is valuable too. Be patient with us though. Play the long game as much as you can. Not every POC goes forward—that’s why we do them to learn. For those on the buying side, I think we need to remember POCs can be an expensive endeavor for the vendors side (time, money, opportunity cost) and we should be as honest and transparent as we can about our plans.

• Your product may help us have a breakthrough: Your product could be a huge game changer for us, and if it is we really do want to know about it.

• We like finding products vs having them pushed on us: If you are selling a product, can you show up in the places we intentionally direct our attention? Physically at conferences? Virtually in blog posts and research reports and such? Whenever possible, I think it’s better to create an insatiable demand for your product so that we come knocking on your door instead of you trying to knock on ours. Less than 1% of the inbound attempts I get lead to partnerships, but the vast majority of outbound (we call you) lead to long-term partnerships. We know what we’re looking for (but sometimes may not know your product exists). I’ll share my favorite places to gather industry info in a future Chamber 🏰 of Tech Secrets.

Most importantly, remember that long-term, value-creating relationships with Enterprises are very lucrative and our spend tends to increase with value-added over time. We also have a lot of really great people you could build relationships with and have a lot of fun with. Play the long game.

5 Snarky Suggestions (of things not to do)

There are a few tactics that I find to be consistently unsuccessful. No offense to those who have tried them, but I’d just like to give an honest perspective about what it feels like to be on my side of the fence.

Source: https://blog.hubspot.com/sales/sales-memes

1. I do not have time tomorrow or later this week: I get a lot of messages with “are you available for a call tomorrow at 10:30am to discuss how _______ can help you ______?”. Honestly, I am never available tomorrow. I have a window of time (2-4pm EDT) where I allow for outside meetings and it usually is booked several weeks out. To be honest, these messages make me feel like the person sending them thinks I only exist to respond to their inquiry. I know that is not the intent. A better approach would be to share just enough [but not too much] about your product’s value add in an initial email, but wait until I have expressed interest and confirmed your product is a fit to even broach the topic of scheduling a meeting. I debate if sending a calendly is helpful: it is if I am interested (or I’ll send you mind in return) and its neutral if I am not. Oh, and please do not send cold meeting request invites and email read receipts. 🙏

2. Don’t reply to your own email over and over and over: I have seen “threads” with 10+ replies, all of the salesperson replying to their previous message. While we’re on that topic, the “Any thoughts Brian?” reply is not very helpful either. Avoid these tactics. Instead be patient and seek to add value. Some companies I have talked to have sent helpful videos or articles about their product or the industry and stepped away to leave the ball in my court. I appreciate this approach a lot.

3. Try not to weaponize quarterly timelines: Some organizations apply pressure to us as customers to try and close a deal on their quarterly timeline. I’m financially literate and I get booking revenue and new customers to meet quarterly targets. It feels really transactional though. I am looking to work with companies that are thinking long-term and want to build a partnership where we both get value over a long time… not companies that want to rapidly close a deal to book revenue and move on. The tactic of “well if we don’t close by the end of the quarter we’re going to have to remove those discounts we agreed to” might occasionally get you your outcome, but it leaves us feeling like we’re not building something long term together. I understand that these pressures may come from executive leadership, be completely true, and be out of the salesperson’s control. Perhaps sharing this bullet will help salespeople have discussions like this with their boss in the future?

4. Replace “professionally persistent” with “patiently persistent”: In the systems world we have a technique called “backoff and retry”. When a request fails, we retry the request again after a certain amount of time has passed, with progressively longer intervals between retries. This allows the server or service to recover from errors or overload conditions. Consider a non-reply to be a “failure” in this case, and begin a backoff and retry cadence until you get a response. I would suggest (in days) 1-10-30-60-90-120-360. This ensures “persistent” doesn’t become “annoying” to potential customers but still lets you follow up in the event your message was missed. Remember your lead could be having internal server errors and be experiencing overload conditions. 🤣 Timing is key, and this approach would raise chances of hitting at a good time.

5. Don’t belittle the primary contact you’re working with: Asking to ladder-up to executives who are going to give approval to the deal can be insulting to the people who are your biggest advocates and are critical to your product’s success in an enterprise. Switch shoes real quick: if you try and jump to an “executive” you’ve made someone who might be very excited about your product feel like they are small and that you are big. On my team, we pick the solution(s) that our best technologists like and recommend. Bottom up. Not top down. Don’t go around those people.

6. Dial people up on the phone the old fashioned way: I never answer cold calls and I can’t think of a single time I have ever responded to a cold call voicemail. If I were in charge of sales, I would focus energy elsewhere. Maybe calls work in some cases? I don’t know. I’m just giving my perspective. Texts are the same. They feel more invasive. Email and LinkedIn seems “appropriate”.

What should you do?

Given my experience on the receiving end and in selling within my own company, here are a few suggestions:

1. Master your product: I reached out to Company A because I was interested in their product and thought it would be a good fit for our enterprise. In 25 minutes (including intros) the salesperson answered every single technical question I had. 🤯 I was shocked with their knowledge of the product and understanding of how it would fit our business. They followed up via email within about 10 minutes and provided everything we needed to move forward with next steps. Wow.

2. Master your customer: read everything they have ever written. Be a customer of their business. Think about what you would do if you were in their situation and might have a need for your product. Rather than assuming they need the hammer you have to sell, consider what nails they might be trying to whack and see if there’s a fit. You might find they actually need a screwdriver (not a hammer) and you don’t have one to sell. If you aren’t sure, just politely ask and seek to understand. Showing up in this way builds trust that can lead to future relationships even if it’s not the right time right now.

3. Bring a friend: if you are selling to someone like me, it’s really helpful to have a technical person available from day 1. If you can’t master the product (which I understand) plan to bring a friend. Tell your boss you need someone who is incentivized by sales outcomes to be your technical partner. On the enterprise side we have limited time, so being able to truly maximize each meeting is important, especially in the beginning.

4. Make a friend: Company B reached out to me and offered to connect when they were in my area of town. They weren’t pushy; they were kind. I agreed to meet. After understanding our usage of an open source version of their product they realized selling right now probably wasn’t the answer and spent the conversation learning about our business and how we work. You can’t sell something that someone doesn’t need… and even if you could… should you? Instead, this person started building a personal relationship over both work and non-work topics. The next time this person emails me, whether at their current company or a future one, you can be sure I will read and reply. Company C reached out to see if we might be interested in their startup. They had a good understanding of what we did and thought it might be a good fit. It turned out it wasn’t the right time for us. I just had dinner with one of Company C’s founders a few days ago and we just talked technology in general and built a more personal relationship. Zero mentions of their product. If there is ever a right time to partner, I know Company C and they will be top of mind.

5. We can all learn from each other. We can all add value to each other’s lives: for my friends who are not in sales, remember that you have a human on the other side of the emails in your inbox that is trying to do their job. They might be able to teach you something new. If nothing else, remember to treat them with kindness. We can all add value to each other, whether through new products or new friendships. There is a power in saying “yes” even when you’re busy.

There has been a lot of hype about AI personalizing sales emails. I expect that is the future. This is likely to increase noise for people like me and may make the entire email channel irrelevant. Think about how to keep making human connections in this ever-changing environment. They will rise above the “cheap” chatter.

One last secret

Let me tell you a secret. You might not realize it, but I am a salesperson, too. Yes, it’s true. While my type of sales is a little different, my role in Enterprise Architecture is very much about developing an idea (my product) and selling its value to others who choose to buy it, either with their decisions to invest in the idea with money / people or by letting it inform the way they work. I have to sell to everyone from software engineers to business leaders, and in between. I am a sales person.

I imagine people selling are facing rejection, fear, leadership pressure, deadlines, timelines, concerns over their job, concerns over reaching goals and quotas, and a host of other concerns. In many of those cases, I can relate.

For those selling, I hope this helps you see my side. For those buying, I hope you’ll be extra kind to folks doing these tough jobs. When we open ourselves to connecting without pressure, we may be surprised at the long-term value we unlock together.

Bonus: my hand written (not ChatGPT) cold email:

This is what I would write to myself as a potential lead. Remember I have never been in this type of sales role so take it for what its worth…

Hi Brian,

I work in sales for SuperDuperCompany. I have been following your blog about The World’s Greatest Project and found is really intriguing. My company has an awesome service/platform called SuperDuperService that has features that do SuperThingA, SuperThingB, and SuperThingC. I think these could be valuable to you so I would love to connect with you and see if we could partner together. Would you be open to an initial conversation?

I’m a big fan of your company and wish you all the success possible.

PS: In case you're unable to respond at this time, I'll follow up in 10 days. Please feel free to reach out to me anytime using the contact information below.

Have a great week!
Brian Salesman

<CONTACT INFO>

** please don’t copy / paste this email and send it to me. 🤣

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